DPP系有机颜料的合成及颜料化研究
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摘要
本论文详细研究了DPP系颜料的合成和颜料化工艺。研究了催化剂种类、缩合闭环用丁二酸二酯种类等因素对DPP系颜料合成的影响。详细地研究了DPP254和DPP255的合成工艺条件。系统研究了催化剂、反应物配比、反应时间、反应温度等因素对产品颜料收率、色相色光以及其它重要性能的影响,并确定了合成高质量DPP254的最佳工艺条件:叔戊醇钠(mol):丁二酸二异丙酯(mol)为5.5,对氯苯甲腈(mol):丁二酸二异丙酯(mol)为1.95,反应温度为110℃,反应时间为4h。收率达85.3%。合成高质量DPP255的最佳工艺:叔戊醇钠(mol):丁二酸二异丙酯(mol)为3,苯腈(mol):丁二酸二异丙酯(mol)为2.4,反应温度为105℃,反应时间为3.5h。收率达62.5%。
采用溶剂法和添加表面处理剂相结合,分别在颜料合成过程中(一步法颜料化)和颜料合成过程后(二步法颜料化)对DPP254进行颜料化处理,系统研究了表面处理剂、溶剂、颜料化时间、颜料化温度等因素对产品颜料色相色光以及其它重要性能的影响,确定了较成熟的颜料化方案工艺条件。对得到的产品颜料进行了色相色光、遮盖力、透明度、晶型、流动性能等性能测试。测试表明,所得产品颜料颜色鲜艳、色光纯正、遮盖力强、流动性好、各方面性能优异,可与汽巴标样相媲美。
The present paper relates to the preparation of l,4-diketopyrrolo-[3,4-C]-pyrroles pigments, the influence of the reaction factors, such as catalyst, succinate etc. The paper researched the preparing of C.I. Pigment Red 254 (DPP 254) and C.I. Pigment Red 255 (DPP 255). Moreover, the influence of the reacting factors, such as catalyst, materials ratio, time, temperature etc on the yield, color, shade and other important properties of DPP pigments were studied. Then the factors were finally defined. DPP 254 was synthesized from 4-Chlorobenzonitrile and di-isopropyl succinate with high yield of 85.3%. The conclusions were drawn as follows: n(sodium tert-butylate):n(di-isopropyl succinate) was 5.5, n(4-chlorobenzonitrile):n(di-isopropyl succinate) was 1.95, the temperature was 110℃, the time was 4h. And DPP 255 was synthesized from benzonitrile and di-isopropyl succinate with high yield of 62.5%. The conclusions were drawn as follows: n(sodium tert-butylate) : n(di-isopropyl succinate) was 3, n(benzonitrile):n(di-isopropyl succinate) was 2.4, the temperature was 105℃, the time was 3.5h.
The paper adopted different conditioning methods, the solvent treatment and using different surface processors, to get the pigmentation of DPP 254 during the synthesis process of pigment (1 step pigmentation) or after it (2 steps pigmentation). The influence of the pigmentation factors, such as surface processor, solvent, time, temperature etc on the color, shade and other important properties of DPP 254 were studied. Then a kind of conditioning method was found and the factors were finally defined. The pigment was tested by color, shade, transparence, crystal shape, fluidity etc. According to the test, the pigment has fresh color, good hiding capability, high fluidity and other excellent capabilities. The pigment can compare beauty with Ciba standard sample.
The paper combined with acquired patent to create a new way of synthesis for preparing N-substituted DPP. Then a part of the synthesis method was attested that it's feasible.
采用溶剂法和添加表面处理剂相结合,分别在颜料合成过程中(一步法颜料化)和颜料合成过程后(二步法颜料化)对DPP254进行颜料化处理,系统研究了表面处理剂、溶剂、颜料化时间、颜料化温度等因素对产品颜料色相色光以及其它重要性能的影响,确定了较成熟的颜料化方案工艺条件。对得到的产品颜料进行了色相色光、遮盖力、透明度、晶型、流动性能等性能测试。测试表明,所得产品颜料颜色鲜艳、色光纯正、遮盖力强、流动性好、各方面性能优异,可与汽巴标样相媲美。
The present paper relates to the preparation of l,4-diketopyrrolo-[3,4-C]-pyrroles pigments, the influence of the reaction factors, such as catalyst, succinate etc. The paper researched the preparing of C.I. Pigment Red 254 (DPP 254) and C.I. Pigment Red 255 (DPP 255). Moreover, the influence of the reacting factors, such as catalyst, materials ratio, time, temperature etc on the yield, color, shade and other important properties of DPP pigments were studied. Then the factors were finally defined. DPP 254 was synthesized from 4-Chlorobenzonitrile and di-isopropyl succinate with high yield of 85.3%. The conclusions were drawn as follows: n(sodium tert-butylate):n(di-isopropyl succinate) was 5.5, n(4-chlorobenzonitrile):n(di-isopropyl succinate) was 1.95, the temperature was 110℃, the time was 4h. And DPP 255 was synthesized from benzonitrile and di-isopropyl succinate with high yield of 62.5%. The conclusions were drawn as follows: n(sodium tert-butylate) : n(di-isopropyl succinate) was 3, n(benzonitrile):n(di-isopropyl succinate) was 2.4, the temperature was 105℃, the time was 3.5h.
The paper adopted different conditioning methods, the solvent treatment and using different surface processors, to get the pigmentation of DPP 254 during the synthesis process of pigment (1 step pigmentation) or after it (2 steps pigmentation). The influence of the pigmentation factors, such as surface processor, solvent, time, temperature etc on the color, shade and other important properties of DPP 254 were studied. Then a kind of conditioning method was found and the factors were finally defined. The pigment was tested by color, shade, transparence, crystal shape, fluidity etc. According to the test, the pigment has fresh color, good hiding capability, high fluidity and other excellent capabilities. The pigment can compare beauty with Ciba standard sample.
The paper combined with acquired patent to create a new way of synthesis for preparing N-substituted DPP. Then a part of the synthesis method was attested that it's feasible.
引文
[1]孙德帅.耐光氧化有机颜料的研究[D].青岛大学.2002,2-4
[2]沈永嘉.有机颜料--品种与应用[M].化学工业出版社.2001,72-78
[3]莫述诚等编.有机颜料[M].化学工业出版社.1991,113-115
[4]缪建明.有机颜料概况与应用性能介绍[J].1997(1),1-5
[5]周春隆.有机颜料物理化学特性及其未来发展趋势(一)[J].染料工业,2000,37(4):1-6
[6]陈荣圻.有机颜料表面改性处理(一)[J].印染,2000,(2):38-40
[7]陈荣圻.有机颜料表面改性处理(二)[J].印染,2000,(3):43-44
[8]陈荣圻.有机颜料表面改性处理(三)[J].印染,2000,(4):44-46
[9]肖刚,孙朝晖.杂环有机颜料的新技术进展(一)[J].上海染料,2001,29(5):30-34
[10]鹏博.DPP系颜料近代进展[J].上海染料,1999,27(4):30-32
[11]周春隆,穆振义.有机颜料化学及工艺学[M].中国石化出版社.2002,98-101
[12]D.G.Farmum,G.Mehta.Process for the preparation of ditert-butyl succinate[J].Tetrahedron Letters,1974,29:2549-2552
[13]中国专利中有关染(颜)料及中间体部分简介[J].染料工业.2000.37(5):41
[14]周春隆.有机颜料工业新技术进展[J].染料与染色,2004,41(1):34-35
[15]周春隆.有机颜料物理化学特性及其未来发展趋势(二)[J].染料工业,2000,37(5):1-5;18
[16]周春隆.有机颜料物理化学特性及其未来发展趋势(三)[J].染料工业,2000,37(6):1-3
[17]梁兴国.1,4-二酮吡咯并吡咯颜料的研究[D].天津大学.1995,13-18
[18]穆振义.吡咯并吡咯二酮(DPP)类颜料及苯腈取代衍生物[J].上海染料,2004,32(5):30-34
[19]周春隆,穆振义.有机颜料--结构、特性及应用[M].化学工业出版社.1997,211-214
[20]周春隆.有机颜料在印刷油墨中的应用[J].上海染料,1999(1):15-17
[21]周春隆.有机颜料在涂料中的应用[J].上海染料,1998,(6):27-29
[22]沈永嘉.一些急待开发的中间体[J].精细化工原料及中间体,2004,(10):2-4
[23]穆振义.吡咯并吡咯二酮(DPP)类颜料及苯腈取代衍生物(二)[J].上海染料,2004,32(6):20-26
[24]Rochat alain C,Cassar Luigi,Iqbal Abul.Preparation of Pyrrolo[3,4-c]pyrooles[P].US 5479949,1986
[25]许剑平.复合型固体超强酸催化合成丁二酸二乙酯的研究[J].化工时代,2001,(9):32-34
[26]何节玉.硅胶担载硫酸铈催化合成丁二酸二乙酯[J].稀土,2004,25(2):10-12
[27]邓德华,许剑平.离子交换树脂催化合成丁二酸二乙酯[J].化工时代,2001,(11):37-39
[28]文瑞明,丁亮中,罗新湘.硫酸氢钠催化合成丁二酸二乙酯[J].广西化工,2002,31(1):3-4
[29]Vowinkl E.Preparation of carboxylic acid esters by oalkyl-N,N'-dicyclohexylisourea[J].Chem Ber,1967,100(1):16-22
[30]Crowe B F.Carbonylation of acetylene with carbon monoxide,hydrogen,and isopropanol[J].Chem &Ind,1960,79(11):1506-1507
[31]Shim S C,Huh K T,Park W H.Carbonylation of acetylene with carbon monoxide,hydrogen,and isopropanol[J].Synth Commun,1987,18(1):59
[32]Hirao N,Nishio S.Reaction of chloride with ethers[J].Kinki Daigaku Kenkyu Hokoku(Journal of the Faculty of Science and Technology,Kinki University),1976,10(11):63-65
[33]Martin Kudschus,Olof Wallquist.Process for the preparation of ditert-butyl succinate[P].US005914426,1998
[34]Parmar A Kaur.Esterification in dry media using ferric perchlorate adsorbed on silica gel[J].Synth Commun,1998,28(15):2821-2826
[35]Banerjee A,Sengupta S,Adak M M.Use of phosphorus pentoxide:Esterification of organic acids[J].J Org Chem,1983,48(18):3106-3108
[36]宋秀娟,覃志忠,张国亮,张凤宝.对甲基苯磺酸催化合成丁二酸二异丙酯[J].化学工业与工程,2006,23(1):93-94;封3
[37]#12
[38]Iqbal Abul,Pfenninger Johannes,Rochat alain C.Pigment blends[P].EP 181290,1986
[39]Jaffe Edward Ephraim,Babler Fridolin.Process for the manufacture of covering diketopyrrolopyrrole pigments[P].EP0337435,1989
[40]Iqbal Abul,Cassar Luigi.Process for dyeing high-molecular organic material,and novel polycyclic pigments[P].US4415685,1983
[41]Zambounis John S,Hao Zhimin.Pyrrolo[3,4-C]pyrroles[P].US5484943,1996
[42]Wettlaufer David G,Nemoto Peter A.(Pyrrolidinyl) phenyl carbamates and related compounds[P].US5591856,1997
[43]Jost Max,Iqbal Abul.N-substituted 1,4-diketopyrrolo-[3,4-C]-pyrroles[P].US4585878,1986
[44]Jahne Gerhard,Geisen Karl.Polycyelic thiazol-2-ylidene amines,processes for their preparation and their use as medicaments[P].US6288093,2001
[45]周春隆.有机颜料合成与颗粒极性调整技术(一)[J].上海染料,2005,33(1):21-31
[46]Hao Zhimin,Iqbel Abul.Two new crystal modifications of a diketopyrrolopyrrole pigment[P].US5646299,1997
[47]杜克生,李光源.颜料染料涂料检验技术[M].化学工业出版社.1988,65-69
[48]Hendi,Shivakumar Basalingappa Newark.Direct preparation of pigmentary pyrrolo-(3,4-C)pyrroles[P].EP0962499A2,1999
[49]韩瑞生,胡进勇,高东颖.对甲苯磺酸催化合成丁二酸二甲酯的研究[J].化学工程师,2000,81(6):3-4
[50]田华荣.丁二酸二甲酯合成工艺改进研究[J].常熟理工学院学报,2005,19(6):37-39
[51]林进,王兰芝,王昭煜.对甲苯磺酸催化合成丁二酸二乙酯[J].河北师范大学学报(自然科学版),1999,23(4):523-524,529
[52]信建峰,马吉海,张树芬,陈韶蕊,李海于.酰氯制备方法综述[J].河北化工,2006,29(11):16-20
[53]奚强,唐杜陵,廖桂茵.氯化亚砜在有机合成中的应用(Ⅰ)氯化亚砜使有机物氯化[J].荆州师专学报(自然科学版),1997,20(5):69-72
[54]蔡宝国,龚钢明,金东元,姜荫.双硬脂酸曲酸酯的制备及应用[J].化学世界,2003,(1):38-40,52-53
[55]韦建国,马向东,沈艳涛,刘江雏.丁二酸单乙酯酰氯的合成[J].应用化工,2002,31(5):20-21
[56]费学宁,贾堤,庄娉,李素清.C.I.颜料红177颜料化的初步研究[J].天津化工,2000,(4):6-7
[57]李梅彤.C.I.颜料红179的合成及颜料化研究[D].天津大学,2005,34-36
[58]周春隆.有机颜料物理化学特性及其未来发展趋势[J].染料工业,2000,37(5):1-5,18
[59]Terrence R.Chamberlain,Craig Thornley.Syntheses for preparing 1,4-diketopyrrolo[3,4-C]pyrroles[P].US6388093,2002
[2]沈永嘉.有机颜料--品种与应用[M].化学工业出版社.2001,72-78
[3]莫述诚等编.有机颜料[M].化学工业出版社.1991,113-115
[4]缪建明.有机颜料概况与应用性能介绍[J].1997(1),1-5
[5]周春隆.有机颜料物理化学特性及其未来发展趋势(一)[J].染料工业,2000,37(4):1-6
[6]陈荣圻.有机颜料表面改性处理(一)[J].印染,2000,(2):38-40
[7]陈荣圻.有机颜料表面改性处理(二)[J].印染,2000,(3):43-44
[8]陈荣圻.有机颜料表面改性处理(三)[J].印染,2000,(4):44-46
[9]肖刚,孙朝晖.杂环有机颜料的新技术进展(一)[J].上海染料,2001,29(5):30-34
[10]鹏博.DPP系颜料近代进展[J].上海染料,1999,27(4):30-32
[11]周春隆,穆振义.有机颜料化学及工艺学[M].中国石化出版社.2002,98-101
[12]D.G.Farmum,G.Mehta.Process for the preparation of ditert-butyl succinate[J].Tetrahedron Letters,1974,29:2549-2552
[13]中国专利中有关染(颜)料及中间体部分简介[J].染料工业.2000.37(5):41
[14]周春隆.有机颜料工业新技术进展[J].染料与染色,2004,41(1):34-35
[15]周春隆.有机颜料物理化学特性及其未来发展趋势(二)[J].染料工业,2000,37(5):1-5;18
[16]周春隆.有机颜料物理化学特性及其未来发展趋势(三)[J].染料工业,2000,37(6):1-3
[17]梁兴国.1,4-二酮吡咯并吡咯颜料的研究[D].天津大学.1995,13-18
[18]穆振义.吡咯并吡咯二酮(DPP)类颜料及苯腈取代衍生物[J].上海染料,2004,32(5):30-34
[19]周春隆,穆振义.有机颜料--结构、特性及应用[M].化学工业出版社.1997,211-214
[20]周春隆.有机颜料在印刷油墨中的应用[J].上海染料,1999(1):15-17
[21]周春隆.有机颜料在涂料中的应用[J].上海染料,1998,(6):27-29
[22]沈永嘉.一些急待开发的中间体[J].精细化工原料及中间体,2004,(10):2-4
[23]穆振义.吡咯并吡咯二酮(DPP)类颜料及苯腈取代衍生物(二)[J].上海染料,2004,32(6):20-26
[24]Rochat alain C,Cassar Luigi,Iqbal Abul.Preparation of Pyrrolo[3,4-c]pyrooles[P].US 5479949,1986
[25]许剑平.复合型固体超强酸催化合成丁二酸二乙酯的研究[J].化工时代,2001,(9):32-34
[26]何节玉.硅胶担载硫酸铈催化合成丁二酸二乙酯[J].稀土,2004,25(2):10-12
[27]邓德华,许剑平.离子交换树脂催化合成丁二酸二乙酯[J].化工时代,2001,(11):37-39
[28]文瑞明,丁亮中,罗新湘.硫酸氢钠催化合成丁二酸二乙酯[J].广西化工,2002,31(1):3-4
[29]Vowinkl E.Preparation of carboxylic acid esters by oalkyl-N,N'-dicyclohexylisourea[J].Chem Ber,1967,100(1):16-22
[30]Crowe B F.Carbonylation of acetylene with carbon monoxide,hydrogen,and isopropanol[J].Chem &Ind,1960,79(11):1506-1507
[31]Shim S C,Huh K T,Park W H.Carbonylation of acetylene with carbon monoxide,hydrogen,and isopropanol[J].Synth Commun,1987,18(1):59
[32]Hirao N,Nishio S.Reaction of chloride with ethers[J].Kinki Daigaku Kenkyu Hokoku(Journal of the Faculty of Science and Technology,Kinki University),1976,10(11):63-65
[33]Martin Kudschus,Olof Wallquist.Process for the preparation of ditert-butyl succinate[P].US005914426,1998
[34]Parmar A Kaur.Esterification in dry media using ferric perchlorate adsorbed on silica gel[J].Synth Commun,1998,28(15):2821-2826
[35]Banerjee A,Sengupta S,Adak M M.Use of phosphorus pentoxide:Esterification of organic acids[J].J Org Chem,1983,48(18):3106-3108
[36]宋秀娟,覃志忠,张国亮,张凤宝.对甲基苯磺酸催化合成丁二酸二异丙酯[J].化学工业与工程,2006,23(1):93-94;封3
[37]#12
[38]Iqbal Abul,Pfenninger Johannes,Rochat alain C.Pigment blends[P].EP 181290,1986
[39]Jaffe Edward Ephraim,Babler Fridolin.Process for the manufacture of covering diketopyrrolopyrrole pigments[P].EP0337435,1989
[40]Iqbal Abul,Cassar Luigi.Process for dyeing high-molecular organic material,and novel polycyclic pigments[P].US4415685,1983
[41]Zambounis John S,Hao Zhimin.Pyrrolo[3,4-C]pyrroles[P].US5484943,1996
[42]Wettlaufer David G,Nemoto Peter A.(Pyrrolidinyl) phenyl carbamates and related compounds[P].US5591856,1997
[43]Jost Max,Iqbal Abul.N-substituted 1,4-diketopyrrolo-[3,4-C]-pyrroles[P].US4585878,1986
[44]Jahne Gerhard,Geisen Karl.Polycyelic thiazol-2-ylidene amines,processes for their preparation and their use as medicaments[P].US6288093,2001
[45]周春隆.有机颜料合成与颗粒极性调整技术(一)[J].上海染料,2005,33(1):21-31
[46]Hao Zhimin,Iqbel Abul.Two new crystal modifications of a diketopyrrolopyrrole pigment[P].US5646299,1997
[47]杜克生,李光源.颜料染料涂料检验技术[M].化学工业出版社.1988,65-69
[48]Hendi,Shivakumar Basalingappa Newark.Direct preparation of pigmentary pyrrolo-(3,4-C)pyrroles[P].EP0962499A2,1999
[49]韩瑞生,胡进勇,高东颖.对甲苯磺酸催化合成丁二酸二甲酯的研究[J].化学工程师,2000,81(6):3-4
[50]田华荣.丁二酸二甲酯合成工艺改进研究[J].常熟理工学院学报,2005,19(6):37-39
[51]林进,王兰芝,王昭煜.对甲苯磺酸催化合成丁二酸二乙酯[J].河北师范大学学报(自然科学版),1999,23(4):523-524,529
[52]信建峰,马吉海,张树芬,陈韶蕊,李海于.酰氯制备方法综述[J].河北化工,2006,29(11):16-20
[53]奚强,唐杜陵,廖桂茵.氯化亚砜在有机合成中的应用(Ⅰ)氯化亚砜使有机物氯化[J].荆州师专学报(自然科学版),1997,20(5):69-72
[54]蔡宝国,龚钢明,金东元,姜荫.双硬脂酸曲酸酯的制备及应用[J].化学世界,2003,(1):38-40,52-53
[55]韦建国,马向东,沈艳涛,刘江雏.丁二酸单乙酯酰氯的合成[J].应用化工,2002,31(5):20-21
[56]费学宁,贾堤,庄娉,李素清.C.I.颜料红177颜料化的初步研究[J].天津化工,2000,(4):6-7
[57]李梅彤.C.I.颜料红179的合成及颜料化研究[D].天津大学,2005,34-36
[58]周春隆.有机颜料物理化学特性及其未来发展趋势[J].染料工业,2000,37(5):1-5,18
[59]Terrence R.Chamberlain,Craig Thornley.Syntheses for preparing 1,4-diketopyrrolo[3,4-C]pyrroles[P].US6388093,2002