杂环有机颜料结晶形态与调整技术(三)
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摘要
本文总结了杂环类有机颜料的结晶形态特性、晶格结构、晶体微观形貌对其颜料应用性能的影响,并讨论了片形、针形、棒形与球形等不同结晶形态有机颜料的获取途径。
The influences of characteristic crystal structure,crystal morphology and sheet-shaped of the heterocyclic organic pigment to their performance of application were summarized in the paper. Also the ways to obtain different characteristic crystal structure organic pigments such as sheet-shaped,needle-shaped,rod-like and sphere-shaped were discussed.
The influences of characteristic crystal structure,crystal morphology and sheet-shaped of the heterocyclic organic pigment to their performance of application were summarized in the paper. Also the ways to obtain different characteristic crystal structure organic pigments such as sheet-shaped,needle-shaped,rod-like and sphere-shaped were discussed.
引文
[1]周春隆.偶氮颜料晶格结构及其特性[J],染料与染色,2017,54(1):1-10;(2):1-15.
[2]Peter Erk.Crystal Desigen of High Perfomancene Pigments[M]//Edwin B Faulkner,Russell J Schwartz.High Performance Pigments.2nd Edition.WILEY-VCH,2009:105,120,395.
[3]Desiraju Gautam R.Crystal engineering:solid state supramolecular synthesis[J].Current Opinion in Solid State and Materials Science,1997,2(4):451-454.
[4]Peter Erk.Crystal design of organic pigments—a prototype discipline of materials science[J].Current Opinion in Solid State and Materials Science,2001,5(2-3):155-160.
[5]Natalia Panina.Crystal Structure and Morphology Prediction of Organic Pigments[D].PDF hosted at the Radboud Repository of the Radboud University Nijmegen,Chapter 6:90,Chapter 5:78.
[6]N Panina,R van de Ven,P Verwer,at al.Polymorph prediction of organic pigments[J].Dyes and Pigments,2008,79(2):183-192.
[7]N Panina,F J J Leusen,F F B J Janssen,et al.Crystal structure prediction of organic pigments:quinacridone as an Example[J]Journal of Applied Crystallography,2007,40(1):105-114.
[8]Natalia Panina,Crystal Structure and Morphology Prediction of Organic Pigments[D].Chaper 4,Polymorph Prediction of Organic Pigments,1982:47.
[9]Silke D Gumbert,Meike K9rbitzer,Edith Alig,et al.Crystal structure and tautomerism of Pigment Yellow 138 determined by X-ray powder diffraction and solid-state NMR[J].Dyes and Pigments,2016,131:364-372.
[10]Peter Erk,Heidi Hengelsberg,Mairi F.Haddow,et al.The innovative momentum of crystal engineering[J].Cryst Eng Comm,2004,6(78):474-483.
[11]N Panina,R van de Ven,P Verwer,et al.Polymorph prediction of organic pigments[J].Dyes and Pigments,2008,79(2):183-192.
[12]A Nangia,G R Desiraju.Supramolecular structures-reason and imagination[J].Acta Crystallogr:1998,54(6-1):934.
[13]J Mizuguchi.Crystal structure of trans-bisbenzimidazo[2,1-b:1',2'-j]benzo[lmn][3,8]-Phenanthroline-6,9-dione,C26H12N4O2[J].Zeitschrift für Kristallographie-New Crystal Structures,2003,218:137-138.
[14]J Mizuguchi,K Tojo.Crystal structure of N,N'-bis(3,5-xylyl)perylene-3,4:9,10-bis(dicarboximide)[J].Zeitschrift für Kristallographie-New Crystal Structures,2001,216(3):375-376.
[15]J Mizuguchi,K Tojo.Electronic Structure of Perylene Pigments as Viewed from the Crystal Structure and Excitonic Interactions[J].J.Phys.Chem.:B,2002,106(4):767-772.
[16]G Klebe,F Graser,E Hdicke,et al.Crystallochromy as a solidstate effect:correlation of molecular conformation,crystal packing and color in perylene-3,4:9,10-bis(dicarboximide)pigments[J].Acta Crystallographica Section B:Structural Science,Crystal Engineering and Materials,1989,45(1):69-77.
[17]Erich F Paulus,Frank J J Leusen,Martin U Schmidt.Crystal structures of quinacridones[J].Cryst Eng Comm,2007,9(2):131-143.
[18]J Mizuguchi,T Senju,M Sakai.Crystal structure of 5,12-dihydro-2,9-dimethylquino[2,3-b]acridine-7,14-dione,C22H16N2O2,at 123Κ[J].Zeitschrift für Kristallographie:New Crystal Structures,2002,217:525-526.
[19]Jin Mizuguchi.Correlation between crystal and electronic structures in diketopyrrolopyrrole pigments as viewed from exciton coupling effects[J].Journal of Physical Chemistry:A,2000,104(9):1817-1821.
[20]Jin Mizuguchi,S Matsumoto.Crystal structure of 3,6-bis(3-cyanophenyl)pyrrolo[3,4-c]pyrrole-1,4-dione,C20H10N4O2[J]Zeitschrift für Kristallographie-New Crystal Structures,2000,215(1):195-196.
[21]Jin Mizuguchi.3,6-Bis(4-tert-butylphenyl)-1,2,4,5-tetrahydropyrrolo[3,4-c]pyrrole-1,4-dione[J].Acta crystallographica,Section C:Crystal Structure Communications,1998,54(10):1482-1484.
[22]J Mizuguchi,A Grubenmann,G Rihs.Structures of 3,6-bis(3-chlorophenyl)pyrrolo[3,4-c]pyrrole-1,4-dione and 3,6-bis(4-chlorophenyl)pyrrolo[3,4-c]pyrrole-1,4-dione[J]Acta Crystallographica,Section B:Structural Science,Crystal Engineering and Materials,1993,49(6):1056-1060.
[23]J Mizuguchi,T Miyazaki.Crystal structure of 3,6-bis(4-biphenylyl)pyrrolo[3,4-c]pyrrole-l,4-dione,C30H20N2O2[J].Zeitschrift für Kristallographie:New Crystal Structures,2002,217(1):43-44.
[24]Jin Mizuguchi.J-aggregate-like Structure and Its Influence on the Electronic Spectrum of 1,4-diketo-3,6-bis(4-biphenylyl)pyrrolo[3,4-c]pyrrole[J].Journal of Imaging Science and Technology,2002,46(3):257-261.
[25]周春隆,穆振義,邱茂林.問答有機顏料[M].修訂版.臺北:福基管理顧問有限公司,2017:148.
[26]周春隆,穆振义.有机颜料化学及工艺学[M].第三版.北京:中国石化出版社,2014:280.
[27]西巴-盖尔基股份有限公司.1,4-二酮基吡咯并吡咯类的混合晶体和固体溶液:CN1066767(C)[P].2001-06-06.
[28]T Senju,J Mizuguchi.Electronic structure of thiazine-indigo pigment on the basis of the crystal structure[J].Journal of Physical Chemistry B,2005:109(16):7649-7653.
[29]T Senju,J Mizuguchi.Crystal structure of(2E)-7-chloro-2-(7-chloro-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-ylidene)-2H-1,4-benzothiazine-3(4H)-one,C16H8Cl2N2O2S2,at 93 K[J].Zeitschrift für Kristallographie:New Crystal Structures,2003,218(1):129-130.
[30]N Panina,R van de Ven,P Verwer,et al.Polymorph prediction of organic pigments[J].Dyes and Pigments,2008,79(2):183-192.
[31]M Bailey.The crystal structure of indanthrone[J].Acta Crystallographica,1955,8:182-185.
[32]CIBA SPECIALTY CHEMICALS HOLDING INC.Preparation of pigmentary 2,9-dichloroquinacridone:EP0643109(A1)[P].1995-03-15.
[33]Peter Erk,Josef Hetzenegger,Arno Boehm.Computer design of perfect additives for perylene red[J].European Coatings Journal,1997(10):906-910.
[34]SCHULZ GREGORY R,SUN CHEMICAL CORPORATION.Process for making perylene pigment compositions:US 20030167971[P].2003-09-11.
[35]CIBA SPECIALTY CHEMICALS HOLDING INC.Preparation of pigmentary 2,9-dichloroquinacridone:EP 0643109(A1)[P].1995-03-15.
[36]Liu Tang-Hao,Cheng Wen-Tung,Huang Kou-Tung,et al.Crystallization and morphology of indanthrone converted from latent pigmentin the solution with photo acid generator[J].Dyes and Pigments,2014,105:137-144.
[37]CIBA-GEIGY CORPORATION.Diketopyrrolopyrrole pigments in platelet form:US 5095122[P].1992-03-10.
[38]CIBA-GEIGY CORPORATION.Isoindoline pigments:US 4262120(A)[P].1981-04-14.
[39]CIBA SPECIALTY CHEMICALS HOLDING INC.Process for preparing a platelet form of 1,4-diketo-3,6-Diphenylpyrrolo-(3,4,c)-pyrrole:EP 604370[P].1994-06-29.
[40]CIBA-GEIGY CORPORATION.2,9-Dichloroquinacridone in Platelet Form:US 5084573(A)[P].1992-01-28.
[41]CIBA SPECIALTY CHEMICALS HOLDING INC,MAURER Marc,RAETZO Niklaus,et al.New 2,9-dichloroquinacridone in platelet form:WO 2008055807(A2)[P].2008-05-15.
[2]Peter Erk.Crystal Desigen of High Perfomancene Pigments[M]//Edwin B Faulkner,Russell J Schwartz.High Performance Pigments.2nd Edition.WILEY-VCH,2009:105,120,395.
[3]Desiraju Gautam R.Crystal engineering:solid state supramolecular synthesis[J].Current Opinion in Solid State and Materials Science,1997,2(4):451-454.
[4]Peter Erk.Crystal design of organic pigments—a prototype discipline of materials science[J].Current Opinion in Solid State and Materials Science,2001,5(2-3):155-160.
[5]Natalia Panina.Crystal Structure and Morphology Prediction of Organic Pigments[D].PDF hosted at the Radboud Repository of the Radboud University Nijmegen,Chapter 6:90,Chapter 5:78.
[6]N Panina,R van de Ven,P Verwer,at al.Polymorph prediction of organic pigments[J].Dyes and Pigments,2008,79(2):183-192.
[7]N Panina,F J J Leusen,F F B J Janssen,et al.Crystal structure prediction of organic pigments:quinacridone as an Example[J]Journal of Applied Crystallography,2007,40(1):105-114.
[8]Natalia Panina,Crystal Structure and Morphology Prediction of Organic Pigments[D].Chaper 4,Polymorph Prediction of Organic Pigments,1982:47.
[9]Silke D Gumbert,Meike K9rbitzer,Edith Alig,et al.Crystal structure and tautomerism of Pigment Yellow 138 determined by X-ray powder diffraction and solid-state NMR[J].Dyes and Pigments,2016,131:364-372.
[10]Peter Erk,Heidi Hengelsberg,Mairi F.Haddow,et al.The innovative momentum of crystal engineering[J].Cryst Eng Comm,2004,6(78):474-483.
[11]N Panina,R van de Ven,P Verwer,et al.Polymorph prediction of organic pigments[J].Dyes and Pigments,2008,79(2):183-192.
[12]A Nangia,G R Desiraju.Supramolecular structures-reason and imagination[J].Acta Crystallogr:1998,54(6-1):934.
[13]J Mizuguchi.Crystal structure of trans-bisbenzimidazo[2,1-b:1',2'-j]benzo[lmn][3,8]-Phenanthroline-6,9-dione,C26H12N4O2[J].Zeitschrift für Kristallographie-New Crystal Structures,2003,218:137-138.
[14]J Mizuguchi,K Tojo.Crystal structure of N,N'-bis(3,5-xylyl)perylene-3,4:9,10-bis(dicarboximide)[J].Zeitschrift für Kristallographie-New Crystal Structures,2001,216(3):375-376.
[15]J Mizuguchi,K Tojo.Electronic Structure of Perylene Pigments as Viewed from the Crystal Structure and Excitonic Interactions[J].J.Phys.Chem.:B,2002,106(4):767-772.
[16]G Klebe,F Graser,E Hdicke,et al.Crystallochromy as a solidstate effect:correlation of molecular conformation,crystal packing and color in perylene-3,4:9,10-bis(dicarboximide)pigments[J].Acta Crystallographica Section B:Structural Science,Crystal Engineering and Materials,1989,45(1):69-77.
[17]Erich F Paulus,Frank J J Leusen,Martin U Schmidt.Crystal structures of quinacridones[J].Cryst Eng Comm,2007,9(2):131-143.
[18]J Mizuguchi,T Senju,M Sakai.Crystal structure of 5,12-dihydro-2,9-dimethylquino[2,3-b]acridine-7,14-dione,C22H16N2O2,at 123Κ[J].Zeitschrift für Kristallographie:New Crystal Structures,2002,217:525-526.
[19]Jin Mizuguchi.Correlation between crystal and electronic structures in diketopyrrolopyrrole pigments as viewed from exciton coupling effects[J].Journal of Physical Chemistry:A,2000,104(9):1817-1821.
[20]Jin Mizuguchi,S Matsumoto.Crystal structure of 3,6-bis(3-cyanophenyl)pyrrolo[3,4-c]pyrrole-1,4-dione,C20H10N4O2[J]Zeitschrift für Kristallographie-New Crystal Structures,2000,215(1):195-196.
[21]Jin Mizuguchi.3,6-Bis(4-tert-butylphenyl)-1,2,4,5-tetrahydropyrrolo[3,4-c]pyrrole-1,4-dione[J].Acta crystallographica,Section C:Crystal Structure Communications,1998,54(10):1482-1484.
[22]J Mizuguchi,A Grubenmann,G Rihs.Structures of 3,6-bis(3-chlorophenyl)pyrrolo[3,4-c]pyrrole-1,4-dione and 3,6-bis(4-chlorophenyl)pyrrolo[3,4-c]pyrrole-1,4-dione[J]Acta Crystallographica,Section B:Structural Science,Crystal Engineering and Materials,1993,49(6):1056-1060.
[23]J Mizuguchi,T Miyazaki.Crystal structure of 3,6-bis(4-biphenylyl)pyrrolo[3,4-c]pyrrole-l,4-dione,C30H20N2O2[J].Zeitschrift für Kristallographie:New Crystal Structures,2002,217(1):43-44.
[24]Jin Mizuguchi.J-aggregate-like Structure and Its Influence on the Electronic Spectrum of 1,4-diketo-3,6-bis(4-biphenylyl)pyrrolo[3,4-c]pyrrole[J].Journal of Imaging Science and Technology,2002,46(3):257-261.
[25]周春隆,穆振義,邱茂林.問答有機顏料[M].修訂版.臺北:福基管理顧問有限公司,2017:148.
[26]周春隆,穆振义.有机颜料化学及工艺学[M].第三版.北京:中国石化出版社,2014:280.
[27]西巴-盖尔基股份有限公司.1,4-二酮基吡咯并吡咯类的混合晶体和固体溶液:CN1066767(C)[P].2001-06-06.
[28]T Senju,J Mizuguchi.Electronic structure of thiazine-indigo pigment on the basis of the crystal structure[J].Journal of Physical Chemistry B,2005:109(16):7649-7653.
[29]T Senju,J Mizuguchi.Crystal structure of(2E)-7-chloro-2-(7-chloro-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-ylidene)-2H-1,4-benzothiazine-3(4H)-one,C16H8Cl2N2O2S2,at 93 K[J].Zeitschrift für Kristallographie:New Crystal Structures,2003,218(1):129-130.
[30]N Panina,R van de Ven,P Verwer,et al.Polymorph prediction of organic pigments[J].Dyes and Pigments,2008,79(2):183-192.
[31]M Bailey.The crystal structure of indanthrone[J].Acta Crystallographica,1955,8:182-185.
[32]CIBA SPECIALTY CHEMICALS HOLDING INC.Preparation of pigmentary 2,9-dichloroquinacridone:EP0643109(A1)[P].1995-03-15.
[33]Peter Erk,Josef Hetzenegger,Arno Boehm.Computer design of perfect additives for perylene red[J].European Coatings Journal,1997(10):906-910.
[34]SCHULZ GREGORY R,SUN CHEMICAL CORPORATION.Process for making perylene pigment compositions:US 20030167971[P].2003-09-11.
[35]CIBA SPECIALTY CHEMICALS HOLDING INC.Preparation of pigmentary 2,9-dichloroquinacridone:EP 0643109(A1)[P].1995-03-15.
[36]Liu Tang-Hao,Cheng Wen-Tung,Huang Kou-Tung,et al.Crystallization and morphology of indanthrone converted from latent pigmentin the solution with photo acid generator[J].Dyes and Pigments,2014,105:137-144.
[37]CIBA-GEIGY CORPORATION.Diketopyrrolopyrrole pigments in platelet form:US 5095122[P].1992-03-10.
[38]CIBA-GEIGY CORPORATION.Isoindoline pigments:US 4262120(A)[P].1981-04-14.
[39]CIBA SPECIALTY CHEMICALS HOLDING INC.Process for preparing a platelet form of 1,4-diketo-3,6-Diphenylpyrrolo-(3,4,c)-pyrrole:EP 604370[P].1994-06-29.
[40]CIBA-GEIGY CORPORATION.2,9-Dichloroquinacridone in Platelet Form:US 5084573(A)[P].1992-01-28.
[41]CIBA SPECIALTY CHEMICALS HOLDING INC,MAURER Marc,RAETZO Niklaus,et al.New 2,9-dichloroquinacridone in platelet form:WO 2008055807(A2)[P].2008-05-15.
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