C.I.颜料红179的合成及颜料化研究
|
摘要
本论文研究了C.I.颜料红179及其中间体3,4,9,10-苝四甲酸二酐(PTCA)的合成工艺条件。以1,8-萘二甲酰亚胺为原料,选用最佳工艺条件合成高纯度的PTCA,收率达到了83.27%,纯度99.02%。并以一甲胺水溶液和PTCA为原料,合成C.I.颜料红179。系统研究了反应时间、温度、介质、物料比、催化剂等因素对颜料收率、色光、色力以及其它重要性能的影响,确定了最佳的工艺条件,使C.I.颜料红179粗品的收率达到了98.56%。
采用研磨法(捏合)和溶剂法相结合对C.I.颜料红179粗品进行颜料化处理,得到高遮盖力型易分散的C.I.颜料红179。又采用了球磨法、添加苝衍生物方法以及酸溶胀法的三结合对C.I.颜料红179粗品进行颜料化处理,得到高透明型易分散的C.I.颜料红179。对得到的两种型号的C.I.颜料红179,进行了色光、着色力、遮盖力、透明性、易分散性、粒度、晶型、热稳定性、耐迁移性、耐溶剂性、流变性能等性能测试。测试表明,所得颜料色光鲜艳、分散性好、着色力强、各种牢度性能优异。
The present paper relates to the preparation of C.I. Pigment Red179 and its intermediate 3,4,9,10-perylenetetracarboxylic dianhydride(PTCA). At first, under the optimum reaction factors, PTCA wassynthesized from 1,8-naphthalimide with high yield of 83.27% and highpurity of 99.02%. Thereafter C.I. Pigment Red 179 was synthesized bycondensing PTCA with monomethyl amine. Moreover, the influence ofthe reacting factors, such as time, temperature, medium, materials ratio,catalyst etc on the yield, shade, tinctorial strength and other importantproperties of C.I. Pigment Red 179 were studied. The final definedfactors make the yield of crude C.I. Pigment Red 179 up to 98.56%.
The paper adopted different conditioning methods and got twodifferent type of C.I. Pigment Red 179 finished, the good hidingpowder type is conditioned with salt ground(kneading) and solventtreatment, the transparent type is conditioned with ball milling, acidswelling and adding so-called X additive. Both types have gooddispersibility, high tinctorial strength and excellent fastness to solvent,migration fastness, weather fastness and light fastness and so on.
采用研磨法(捏合)和溶剂法相结合对C.I.颜料红179粗品进行颜料化处理,得到高遮盖力型易分散的C.I.颜料红179。又采用了球磨法、添加苝衍生物方法以及酸溶胀法的三结合对C.I.颜料红179粗品进行颜料化处理,得到高透明型易分散的C.I.颜料红179。对得到的两种型号的C.I.颜料红179,进行了色光、着色力、遮盖力、透明性、易分散性、粒度、晶型、热稳定性、耐迁移性、耐溶剂性、流变性能等性能测试。测试表明,所得颜料色光鲜艳、分散性好、着色力强、各种牢度性能优异。
The present paper relates to the preparation of C.I. Pigment Red179 and its intermediate 3,4,9,10-perylenetetracarboxylic dianhydride(PTCA). At first, under the optimum reaction factors, PTCA wassynthesized from 1,8-naphthalimide with high yield of 83.27% and highpurity of 99.02%. Thereafter C.I. Pigment Red 179 was synthesized bycondensing PTCA with monomethyl amine. Moreover, the influence ofthe reacting factors, such as time, temperature, medium, materials ratio,catalyst etc on the yield, shade, tinctorial strength and other importantproperties of C.I. Pigment Red 179 were studied. The final definedfactors make the yield of crude C.I. Pigment Red 179 up to 98.56%.
The paper adopted different conditioning methods and got twodifferent type of C.I. Pigment Red 179 finished, the good hidingpowder type is conditioned with salt ground(kneading) and solventtreatment, the transparent type is conditioned with ball milling, acidswelling and adding so-called X additive. Both types have gooddispersibility, high tinctorial strength and excellent fastness to solvent,migration fastness, weather fastness and light fastness and so on.
引文
[l] Kardos M. Vat dyes of the anthracene series. DE275220, 1913.
[2] Herbst. W, Hunger. K. Industrial Organic Pigments. Second Edition. Weiheim (Federal Republic of Germany): VCH Verlagsgesellschaft mbH, 1997: 477.
[3] 黄德音,段学辉,蓝闽波. 苝四羧酸类有机光电材料研究进展.感光材料,1996,(5): 3-11.
[4] 莫述诚,陈洪,施印华.有机颜料.北京:化学工业出版社,1988.
[5] 黄德音,段学辉,刘燕刚,等.苝四羧酸多联体化合物的合成及其光谱特性研究. 感光科学与光化学,1999,17(1): 10-16.
[6] Akasaki Y, Aonuma H, Nukada K, et al. Electrophotographic photoreceptor having an electric charge generating layer comprising a pyrylium compound. US5024911, 1991.
[7] Forrst S R, Kaplan M L, Schmidt P H. Organic-on-inorganic semiconductor contract barrier diodes. J. Appl. Phys. 1984, 55(6): 1492.
[8] Roland Stolarski. Krzysztof J.Fiksinski. Fluorescent perylene dyes for liquid crystal displays. Dyes and Pigments. 1994, 24(4): 295-303.
[9] Vanewyk R L. Anisotropic fluorophores for liquid crystal displays. Display, 1986, 10:155.
[10] American Cyanamid Company. Chemiluminescent composition. US4678608, 1987.
[11] Michael P, O'Neil, Mark P, et al. Picosecond optical switching based on biphotonic excitation of an electron donor acceptor donor molecule. Science. 1992, 257: 63.
[12] Katsume T, Hiramoto M, Yokoyama M. High photon conversion in a light transducer combining organic electroluminesecent diode with photoresponsive organic pigment film. Apple Phys Lett. 1994, 64(19): 2546.
[13] Malun sadrai. Lasing action in a family of perylene derivatives. J. Phys Phem. 1992, 96:7988.
[14] 李绍武. 汽车涂料用高档有机颜料的发展. 表面工程咨询. 2004,5.
[15] Ciba-Geigy Corporation. Novel modification of perylenetetracarboxylic acid-bis-(3,5–dimethylphenyl)imide. US4404385, 1983.
[16] General Aniline & Film Corporation. Preparation of N,N'-diaryl derivatives of perylene diimid. US2543747, 1948.
[17] Hoechst Aktiengesellschaft. New dyestuff of the perylene tetracarboxylic acid series. US2905685, 1971.
[18] BASF Aktiengesellschaft. Perylene-3,4,9,10-tetracarboxylic diimide pigment, its manufacture and its use. DE2545701, 1975.
[19] BASF Aktiengesellschaft. Perylene-3,4,9,10-tetracarboxylic diimide pigment, its manufacture and its use. DE2546266, 1975.
[20] Allied Chemical Corporation. Novel perylenetetracarboxylic diimide compositions. US3554776, 1971.
[21] Ciba-Geigy Corporation. Process for the manufacture of a red pigment of the perylene series. GB1370433, 1974.
[22] Hoechst Aktiengesellschaft. Process for the preparation of N,N '-dimethylperylene-3,4,9,10-tetracarboxylic diimide in high-hiding pigment form. EP0318022, 1988.
[23] 日本化药株式会社,苝类颜料的制造法. JP48-20007, 1973.
[24] BASF Aktiengesellschaft. Process for upgrading the color value of 3,4,9,10-tetracarboxylic acid N,N '-bis-methylimide. US4189582, 1978.
[25] 沈永嘉. 有机颜料品种与应用. 北京: 化学工业出版社,2001, 22～36.
[26] 朱骥良,吴申年.颜料工艺学. 北京: 化学工业出版社,2001, 27～41.
[27] 周春隆,穆振义. 有机颜料结构、特性及应用. 北京: 化学工业出版社,2002, 198～217.
[28] Herbst. W, Hunger. K. Industrial Organic Pigments. Second Edition. Weiheim (Federal Republic of Germany): VCH Verlagsgesellschaft mbH, 1997: 24～44.
[29] 周春隆,穆振义. 有机颜料化学与工艺学. 北京: 中国石化出版社, 1997, 241.
[30] 周春隆,穆振义. 有机颜料结构、特性及应用. 北京: 化学工业出版社,2002, 287～320.
[31] Herbst. W, Hunger. K. Industrial Organic Pigments. Second Edition. Weiheim (Federal Republic of Germany): VCH Verlagsgesellschaft mbH, 1997: 475.
[32] Ciba-Geigy A.G.. Process for the manufacture of a red pigment of the perylene series. DE2153087, 1972.
[33] Mobay Chemical Corporation. Process for the conditioning an organic pigment. US4432796, 1984.
[34] Hoechst Aktiengesellschaft. Process for the preparation of N,N′-dimethylperylene-3,4,9,10-tetracarboxylic diimide in high-hiding pigment formus. US5110931, 1992.
[35] 张天永,周春隆. 还原染料类颜料及其颜料化技术. 染料工业,1995,32(1): 11.
[36] BASF Aktiengesellschaft. Pigment colored compositions and mixtures. GB923721, 1963.
[37] Hoechst Aktiengesellschaft. Inner salts based on ammonium and sulfonate groups of perylene-3,4,9,10-tetracarboxylic andderivatives thereof. US5248774, 1993.
[38] Miles Inc. Process for the continuous preparation of perylenetetracarboxylic diimides. US5247088, 1993.
[39] Hoechst Aktiengesellschaft. Process for the preparation of 3,4,9,10-perylenetetracarboxylic acid diimide. US4588814, 1986.
[40] BIOS.1484, 21.
[41] P. Erk, J. Hetzenegger, A. B?hm. Crystal habit in paint pigments. Eur. Coating J. 1997, 906.
[2] Herbst. W, Hunger. K. Industrial Organic Pigments. Second Edition. Weiheim (Federal Republic of Germany): VCH Verlagsgesellschaft mbH, 1997: 477.
[3] 黄德音,段学辉,蓝闽波. 苝四羧酸类有机光电材料研究进展.感光材料,1996,(5): 3-11.
[4] 莫述诚,陈洪,施印华.有机颜料.北京:化学工业出版社,1988.
[5] 黄德音,段学辉,刘燕刚,等.苝四羧酸多联体化合物的合成及其光谱特性研究. 感光科学与光化学,1999,17(1): 10-16.
[6] Akasaki Y, Aonuma H, Nukada K, et al. Electrophotographic photoreceptor having an electric charge generating layer comprising a pyrylium compound. US5024911, 1991.
[7] Forrst S R, Kaplan M L, Schmidt P H. Organic-on-inorganic semiconductor contract barrier diodes. J. Appl. Phys. 1984, 55(6): 1492.
[8] Roland Stolarski. Krzysztof J.Fiksinski. Fluorescent perylene dyes for liquid crystal displays. Dyes and Pigments. 1994, 24(4): 295-303.
[9] Vanewyk R L. Anisotropic fluorophores for liquid crystal displays. Display, 1986, 10:155.
[10] American Cyanamid Company. Chemiluminescent composition. US4678608, 1987.
[11] Michael P, O'Neil, Mark P, et al. Picosecond optical switching based on biphotonic excitation of an electron donor acceptor donor molecule. Science. 1992, 257: 63.
[12] Katsume T, Hiramoto M, Yokoyama M. High photon conversion in a light transducer combining organic electroluminesecent diode with photoresponsive organic pigment film. Apple Phys Lett. 1994, 64(19): 2546.
[13] Malun sadrai. Lasing action in a family of perylene derivatives. J. Phys Phem. 1992, 96:7988.
[14] 李绍武. 汽车涂料用高档有机颜料的发展. 表面工程咨询. 2004,5.
[15] Ciba-Geigy Corporation. Novel modification of perylenetetracarboxylic acid-bis-(3,5–dimethylphenyl)imide. US4404385, 1983.
[16] General Aniline & Film Corporation. Preparation of N,N'-diaryl derivatives of perylene diimid. US2543747, 1948.
[17] Hoechst Aktiengesellschaft. New dyestuff of the perylene tetracarboxylic acid series. US2905685, 1971.
[18] BASF Aktiengesellschaft. Perylene-3,4,9,10-tetracarboxylic diimide pigment, its manufacture and its use. DE2545701, 1975.
[19] BASF Aktiengesellschaft. Perylene-3,4,9,10-tetracarboxylic diimide pigment, its manufacture and its use. DE2546266, 1975.
[20] Allied Chemical Corporation. Novel perylenetetracarboxylic diimide compositions. US3554776, 1971.
[21] Ciba-Geigy Corporation. Process for the manufacture of a red pigment of the perylene series. GB1370433, 1974.
[22] Hoechst Aktiengesellschaft. Process for the preparation of N,N '-dimethylperylene-3,4,9,10-tetracarboxylic diimide in high-hiding pigment form. EP0318022, 1988.
[23] 日本化药株式会社,苝类颜料的制造法. JP48-20007, 1973.
[24] BASF Aktiengesellschaft. Process for upgrading the color value of 3,4,9,10-tetracarboxylic acid N,N '-bis-methylimide. US4189582, 1978.
[25] 沈永嘉. 有机颜料品种与应用. 北京: 化学工业出版社,2001, 22～36.
[26] 朱骥良,吴申年.颜料工艺学. 北京: 化学工业出版社,2001, 27～41.
[27] 周春隆,穆振义. 有机颜料结构、特性及应用. 北京: 化学工业出版社,2002, 198～217.
[28] Herbst. W, Hunger. K. Industrial Organic Pigments. Second Edition. Weiheim (Federal Republic of Germany): VCH Verlagsgesellschaft mbH, 1997: 24～44.
[29] 周春隆,穆振义. 有机颜料化学与工艺学. 北京: 中国石化出版社, 1997, 241.
[30] 周春隆,穆振义. 有机颜料结构、特性及应用. 北京: 化学工业出版社,2002, 287～320.
[31] Herbst. W, Hunger. K. Industrial Organic Pigments. Second Edition. Weiheim (Federal Republic of Germany): VCH Verlagsgesellschaft mbH, 1997: 475.
[32] Ciba-Geigy A.G.. Process for the manufacture of a red pigment of the perylene series. DE2153087, 1972.
[33] Mobay Chemical Corporation. Process for the conditioning an organic pigment. US4432796, 1984.
[34] Hoechst Aktiengesellschaft. Process for the preparation of N,N′-dimethylperylene-3,4,9,10-tetracarboxylic diimide in high-hiding pigment formus. US5110931, 1992.
[35] 张天永,周春隆. 还原染料类颜料及其颜料化技术. 染料工业,1995,32(1): 11.
[36] BASF Aktiengesellschaft. Pigment colored compositions and mixtures. GB923721, 1963.
[37] Hoechst Aktiengesellschaft. Inner salts based on ammonium and sulfonate groups of perylene-3,4,9,10-tetracarboxylic andderivatives thereof. US5248774, 1993.
[38] Miles Inc. Process for the continuous preparation of perylenetetracarboxylic diimides. US5247088, 1993.
[39] Hoechst Aktiengesellschaft. Process for the preparation of 3,4,9,10-perylenetetracarboxylic acid diimide. US4588814, 1986.
[40] BIOS.1484, 21.
[41] P. Erk, J. Hetzenegger, A. B?hm. Crystal habit in paint pigments. Eur. Coating J. 1997, 906.