용매 열처리법을 통한 diketopyrrolopyrroles 화합물의 안료화 및 그 특성

김재환; 양석원; 김대성; 우관주; 이근대; 박성수; Jae Hwan Kim; Seok Won Yang; Dae-Sung Kim; Guan Zhu Wu; Gun-Dae Lee; Seong Soo Park

Applied Chemistry for Engineering, Vol.25, No.4, 357-362, August, 2014

Export Citation

용매 열처리법을 통한 diketopyrrolopyrroles 화합물의 안료화 및 그 특성

Pigmentation of Diketopyrrolopyrroles Compound through Solvent Thermal-treatment and Its Property

김재환, 양석원, 김대성¹, 우관주², 이근대 ², 박성수 ^{2, †}

(주) 퍼스트칼라
¹한국세라믹기술원
²부경대학교 공업화학과

Jae Hwan Kim, Seok Won Yang, Dae-Sung Kim¹, Guan Zhu Wu², Gun-Dae Lee², and Seong Soo Park^{2, †}

First Color Co. Ltd., Kyounggi-do 429-914, Korea
¹Eco Composite Materials Lab, Korea Institute of Ceramic Engineering & Technology, Seoul 153-801, Korea
²Department of Industrial Chemistry, Pukyong National University, Busan 608-739, Korea

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초록

본 연구에서는 높은 은폐력과 선명한 색상을 나타내는 diketopyrrolopyrroles (DPP) red 254 안료를 제조하기 위하여 미리 합성한 DPP red 254 crude를 용매 열처리 온도, 유도체 첨가 또는 볼밀링 조건들이 조합된 용매 열처리 공정을 통하여 얻어진 시료들의 물성을 비교 분석하였다. 시료의 특성은 FT-IR, UV-Vis 분광기, TEM, PSA, BET surface area analyzer, viscometer 및 spectrophotometer를 이용하여 분석하였다. 합성한 DPP red 254 crude를 볼밀링 나노화하고 용매 열처리하는 방법이 매우 효과적인 안료화 공정임을 확인하였다.

To prepare diketopyrrolopyrrole (DPP) red 254 pigment with high shield and bright color, DPP red 254 crude previously synthesized was treated at various thermal-treat temperature, addition derivative and ball-milling. The properties of samples were measured by the means of FT-IR, UV-Vis spectroscopy, TEM, PSA, BET surface area analyzer, viscometer and pectrophotometer. It was found that solvent thermal-treatment of the sample prepared after ball-milling as nano-scale was very effective method in pigmentation process.

Keywords:Diketopyrrolopyrrole;Pigments Red 254;Solvent treatment;Modification

[References]

Kim JT, Kim TW, Heo JJ, Eun SE, Joo JP, Chun JK, Ju CS, Korean Chem. Eng. Res., 44(2), 114 (2006)
Rochat AC, Cassar L, Iqbal A, Preparation of pyrrolo[3,4-c]pyrroles, US Patent, 4,579,949 (1986)
Lunak S, Vynuchal J, Vala M, Havel L, Hrdina R, Dyes & Pigments, 82, 102 (2009)
Faulkner EB, Schwartz RJ, High Performance Pigments, 2nd ed., 165-187, Wiley-VCH, Weinheim, DE (2009)
Cao DR, Liu QL, Zeng WJ, Han SH, Peng JB, Liu SP, J. Polym. Sci. A: Polym. Chem., 44(8), 2395 (2006)
Zhang GQ, Liu K, Li Y, Yanga MJ, Polym. Inter., 58, 665 (2009)
Rabindranath AR, Zhu Y, Zhang K, Tieke B, Polymer, 50(7), 1637 (2009)
Fischer GM, Zumbusch A, Daltrozzo E, Angew. Chem. Inter. Edit., 46, 3750 (2007)
Minashima H, Tomiya N, Murohoshi T, Process for producing dichlorodiketo pyrrolopyrrole pigment of the α modification, dichlorodiketopyrrolopyrrole pigment of the α modification produced by the process, and coloring composition using the same, US Patent, 7,431,762 (2008)
Sato T, Omura T, Murohoshi T, Takabatake Y, Ariyoshi Y, Alpha-diketopyrrolo pyrrole pigment, coloring composition containing the same, and red film, US Patent, 20,100,009,214 (2010)
Hao Z, Herren F, Iqbal A, Crystal modification of a diketopyrrolopyrrole pigment, US Patent, 5,591,865 (1997)
Ruch T, Wallquist O, Crystal modification of a diketopyrrolopyrrole pigment, US Patent, 5,871,575 (1999)
Herbst W, Hunger K, Industrial Organic Pigments, 3rd ed., 12-141, Wiley-VCH, Weinheim DE (2004)
Koo HS, Chen M, Pan PC, Thin Solid Films, 515(3), 896 (2006)
Kaul BL, Solvent-free process for the preparation of diketopyrrolopyrrole derivatives, US Patent, 7,728,139 (2010)
Shaabani A, Dabiri M, Bazgir A, Gharanjig K, Dyes & Pigments, 71, 68 (2006)
Saltzman B, Principles of Color Technology, A Wiley- Interscience Publication, 7-8. NJ, USA (1981)
Hunt RWG, Pointer MR, Measuring Colour, 33-37, 4th ed., John Wiley & Sons NJ, USA (2011)

[Related Articles]

[1] Kim JT, Kim TW, Heo JJ, Eun SE, Joo JP, Chun JK, Ju CS, Korean Chem. Eng. Res., 44(2), 114 (2006)

[2] Rochat AC, Cassar L, Iqbal A, Preparation of pyrrolo[3,4-c]pyrroles, US Patent, 4,579,949 (1986)

[3] Lunak S, Vynuchal J, Vala M, Havel L, Hrdina R, Dyes & Pigments, 82, 102 (2009)

[4] Faulkner EB, Schwartz RJ, High Performance Pigments, 2nd ed., 165-187, Wiley-VCH, Weinheim, DE (2009)

[5] Cao DR, Liu QL, Zeng WJ, Han SH, Peng JB, Liu SP, J. Polym. Sci. A: Polym. Chem., 44(8), 2395 (2006)

[6] Zhang GQ, Liu K, Li Y, Yanga MJ, Polym. Inter., 58, 665 (2009)

[7] Rabindranath AR, Zhu Y, Zhang K, Tieke B, Polymer, 50(7), 1637 (2009)

[8] Fischer GM, Zumbusch A, Daltrozzo E, Angew. Chem. Inter. Edit., 46, 3750 (2007)

[9] Minashima H, Tomiya N, Murohoshi T, Process for producing dichlorodiketo pyrrolopyrrole pigment of the α modification, dichlorodiketopyrrolopyrrole pigment of the α modification produced by the process, and coloring composition using the same, US Patent, 7,431,762 (2008)

[10] Sato T, Omura T, Murohoshi T, Takabatake Y, Ariyoshi Y, Alpha-diketopyrrolo pyrrole pigment, coloring composition containing the same, and red film, US Patent, 20,100,009,214 (2010)

[11] Hao Z, Herren F, Iqbal A, Crystal modification of a diketopyrrolopyrrole pigment, US Patent, 5,591,865 (1997)

[12] Ruch T, Wallquist O, Crystal modification of a diketopyrrolopyrrole pigment, US Patent, 5,871,575 (1999)

[13] Herbst W, Hunger K, Industrial Organic Pigments, 3rd ed., 12-141, Wiley-VCH, Weinheim DE (2004)

[14] Koo HS, Chen M, Pan PC, Thin Solid Films, 515(3), 896 (2006)

[15] Kaul BL, Solvent-free process for the preparation of diketopyrrolopyrrole derivatives, US Patent, 7,728,139 (2010)

[16] Shaabani A, Dabiri M, Bazgir A, Gharanjig K, Dyes & Pigments, 71, 68 (2006)

[17] Saltzman B, Principles of Color Technology, A Wiley- Interscience Publication, 7-8. NJ, USA (1981)

[18] Hunt RWG, Pointer MR, Measuring Colour, 33-37, 4th ed., John Wiley & Sons NJ, USA (2011)