Isoindoline계 황색 화합물의 환경친화적 합성 및 이의 특성

김송혁; 김재환; 양석원; 이원기; 이근대; 박성수; Song Hyuk Kim; Jae Hwan Kim; Seok Won Yang; Won-Ki Lee; Gun-Dae Lee; Seong Soo Park

Applied Chemistry for Engineering, Vol.26, No.1, 74-79, February, 2015

Export Citation

Isoindoline계 황색 화합물의 환경친화적 합성 및 이의 특성

Eco-friend Synthesis of Isoindoline Yellow Compound and its Properties

김송혁, 김재환, 양석원, 이원기¹, 이근대 ², 박성수 ^{2, †}

(주)퍼스트칼라
¹부경대학교 고분자공학과
²부경대학교 공업화학과

Song Hyuk Kim, Jae Hwan Kim, Seok Won Yang, Won-Ki Lee¹, Gun-Dae Lee², and Seong Soo Park^{2, †}

First Color Co. Ltd., Kyounggi-do 429-914, Korea
¹Department of Polymer Engineering, Pukyong National University, Busan 608-739, Korea
²Department of Industrial Chemistry, Pukyong National University, Busan 608-739, Korea

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초록

본 연구에서는 계면활성제를 사용하지 않는 친환경적 방법으로 붉은 계통의 노란 색상을 띄는 높은 내열성을 가진 isoindoline 화합물을 합성하기 위하여 다양한 반응 온도에서 여러 구조의 isoindoline 유도체를 첨가하여 합성한 후, 이를 고압 반응기에서 온도, 시간을 조절하여 결정화하였다. 시료들의 화학적 구조, 입자 형상 및 크기, 색상, 광학적 특성은 각각 FT-IR, FE-SEM 및 PSA, 색차계, UV-Vis 분광기, 제타 포텐샬을 이용하여 측정하여 비교 분석하였다. 유도체를 첨가한 후 결정화 처리하여 높은 내열성, 균일한 입도분포, 우수한 분산성의 isoindoline 화합물을 수득하였고 합성 조건에 따른 색상 변화 경향성을 확인할 수 있었다.

In this study, to obtain isoindoline compounds with the high thermal resistance and reddish yellow color using an environmental friendly method without the use of any surfactants, isoindoline derivatives with different structures were added at various reaction temperatures for the synthesis and the product was then crystallized by controlling temperatures and times in autoclave. Chemical structures, particle sizes, color differences, and optical properties were evaluated by the means of FT-IR, FE-SEM, UV-Vis spectroscopy, PSA (particle size analyzer) and Zeta potential analyzer. The samples with an enhanced dispersibility, highly thermal resistance, uniform particle sizes were achieved possibly due to the addition of isoindoline derivatives into the crystallization processing mixtures. The color change trend was also observed depending upon synthesis conditions.

Keywords:isoindoline;yellow pigment;P.Y. 139 (Pigment yellow 139);derivatives;pigment

[References]

Marti M, Fabregat G, Azambuja DS, Aleman C, Armelin E, Prog. Org. Coat., 73, 321 (2012)
Hainz R, Allaz J, Schroeder D, Isometric isoindoline yellow pigment, US Patent, 8,075,683 (2011)
Faulkner EB, Schwartz RJ, High Performance Pigments, 2nd ed., 221-241, Wiley-VCH, Weinheim, DE (2009)
Herbst W, Hunger K, Wilker G, Ohleier H, Winter R, Industrial Organic Pigments: Production, Properties, Applications, 3nd ed., 31-419, Wiley-VCH, Weinheim, DE (2005)
Baba K, Mori T, Nakatsuka K, Photosensitive coloring composition, and color filter and liquid crystal display panel using the same, US Patent, 6,653,031 (2003)
Philippe B, Michel F, Fritz H, Mcalpine MA, isoindoline pigment having improved low shear dispersibility, US Patent, 6,143,067 (2000)
Garcia MT, Ribosa I, Guindulain T, Laeal JS, Rego JV, Environ. Pollut., 111, 169 (2001)
Cserhati T, Forgacs E, Oros G, Environ. Int., 28, 337 (2002)
Sangeetha S, Basha R, Sreeram KJ, sangilimuthu SN, Nir BU, Dyes Pigments., 94, 548 (2012)
Novaconi S, Vaszilcsin N, Mater. Lett., 95, 59 (2013)
Iqbal Z, Lyubimtsev A, Hanacka M, Zieglera T, Tetrahedron Lett., 50, 5681 (2009)
Tamgho I, Engle JT, Ziegler CJ, Tetrahedron Lett., 54, 6114 (2013)
Makarewicz E, Cysewski P, Michalik A, Ziołkowska D, Dyes Pigments, 96, 338 (2013)
ASTM Standard D 4187-82, Zeta potential of colloids in water and waste water, Am. Soc. for Testing & Mater. (1985)
Hare CH, Paint film degradation: mechanisms and control, 71-77, The Society for Protective Coatings, Pittsburgh, USA (2001)
Herbst W, Hunger K, Industrial Organic Pigments, 3rd ed., 12-261, Wiley-VCH, Weinheim. DE (2004)
Mengual O, Meunier G, Cayre I, Puech K, Snabre P, Talanta, 50, 445 (1999)
Lincke G, Dyes Pigments, 59, 1 (2003)
Atodiresei GV, Sandu IG, Tulbure EA, Vasilache V, Butunaru R, Rev. Chim., 64, 165 (2013)
Choi J, Sakong C, Choi JH, Chun Y, Kim JP, Dyes Pigments, 90, 82 (2011)
Sidir YG, Sidir I, Berber H, Tasal E, J. Mol. Liq., 162, 148 (2011)

[Related Articles]

[1] Marti M, Fabregat G, Azambuja DS, Aleman C, Armelin E, Prog. Org. Coat., 73, 321 (2012)

[2] Hainz R, Allaz J, Schroeder D, Isometric isoindoline yellow pigment, US Patent, 8,075,683 (2011)

[3] Faulkner EB, Schwartz RJ, High Performance Pigments, 2nd ed., 221-241, Wiley-VCH, Weinheim, DE (2009)

[4] Herbst W, Hunger K, Wilker G, Ohleier H, Winter R, Industrial Organic Pigments: Production, Properties, Applications, 3nd ed., 31-419, Wiley-VCH, Weinheim, DE (2005)

[5] Baba K, Mori T, Nakatsuka K, Photosensitive coloring composition, and color filter and liquid crystal display panel using the same, US Patent, 6,653,031 (2003)

[6] Philippe B, Michel F, Fritz H, Mcalpine MA, isoindoline pigment having improved low shear dispersibility, US Patent, 6,143,067 (2000)

[7] Garcia MT, Ribosa I, Guindulain T, Laeal JS, Rego JV, Environ. Pollut., 111, 169 (2001)

[8] Cserhati T, Forgacs E, Oros G, Environ. Int., 28, 337 (2002)

[9] Sangeetha S, Basha R, Sreeram KJ, sangilimuthu SN, Nir BU, Dyes Pigments., 94, 548 (2012)

[10] Novaconi S, Vaszilcsin N, Mater. Lett., 95, 59 (2013)

[11] Iqbal Z, Lyubimtsev A, Hanacka M, Zieglera T, Tetrahedron Lett., 50, 5681 (2009)

[12] Tamgho I, Engle JT, Ziegler CJ, Tetrahedron Lett., 54, 6114 (2013)

[13] Makarewicz E, Cysewski P, Michalik A, Ziołkowska D, Dyes Pigments, 96, 338 (2013)

[14] ASTM Standard D 4187-82, Zeta potential of colloids in water and waste water, Am. Soc. for Testing & Mater. (1985)

[15] Hare CH, Paint film degradation: mechanisms and control, 71-77, The Society for Protective Coatings, Pittsburgh, USA (2001)

[16] Herbst W, Hunger K, Industrial Organic Pigments, 3rd ed., 12-261, Wiley-VCH, Weinheim. DE (2004)

[17] Mengual O, Meunier G, Cayre I, Puech K, Snabre P, Talanta, 50, 445 (1999)

[18] Lincke G, Dyes Pigments, 59, 1 (2003)

[19] Atodiresei GV, Sandu IG, Tulbure EA, Vasilache V, Butunaru R, Rev. Chim., 64, 165 (2013)

[20] Choi J, Sakong C, Choi JH, Chun Y, Kim JP, Dyes Pigments, 90, 82 (2011)

[21] Sidir YG, Sidir I, Berber H, Tasal E, J. Mol. Liq., 162, 148 (2011)