반응성 아조염료로 착색한 PMMA의 성질

금내리; 허지원; Neri Geum; Ji-Won Heo

Journal of the Korean Industrial and Engineering Chemistry, Vol.17, No.4, 426-431, August, 2006

Export Citation

반응성 아조염료로 착색한 PMMA의 성질

Properties of PMMA Dyed with Reactive Azo Dye

금내리^†, 허지원

단국대학교 첨단과학대학 화학과

Neri Geum^†, and Ji-Won Heo

Department of Chemistry, Dankook University, Cheonan 330-714, Korea

E-mail:

초록

Poly(methyl methacrylate) (PMMA)의 착색을 위하여 아크릴 그리고 비닐설폰기를 가지는 청색 및 오렌지 아조 염료들을 6-bromo-2-cyano-4-nitroaniline과 2,5-dimethoxy-4-(vinylsulfonyl)benzenamine을 3-acrylamido-(N,N-diethylamino) benzene과 3-methyl-(N,N-diethylamino)benzene의 아조 짝지음 반응을 이용하여 각각 합성하였다. 또한 알릴기를 가지는 염료는 비닐설폰과 allylamine과의 반응에 의하여 제조하였다. PMMA의 착색은 아크릴, 비닐설폰 그리고 알릴 작용기를 가지는 염료를 직접 methyl methacrylate (MMA)와 공중합하거나, MMA와 공중합한 고분자염료 및 반응성기가 없는 염료 2를 직접 MMA에 용해하여 중합과 동시에 착색하였다. 3가지로 착색한 PMMA의 염색 견뢰도를 여러 환경 조건에서 염료의 용해도를 비교하여 평가하였다.

Acryl and vinyl sulfone functionalized blue and orange azo dyes were prepared by the coupling reaction of 6-bromo-2-cyano-4-nitroaniline and 2,5-dimethoxy-4-(vinylsulfonyl)benzenamine with 3-acrylamido-(N,N-diethylamino)benzene and 3-methyl-(N,N-diethylamino)benzene, respectively, for the coloring of poly(methyl methacrylate) (PMMA). Allyl functionalized dye was also prepared by reacting vinyl sulfone-containing dye with allylamine. Three types of dyeing method were used: the copolymerization of reactive dye with methyl methacrylate (MMA) and dyeing by polymerization of MMA in the presence of polymeric dye and dye 2 without reactive function. The color fastness for the three PMMAs were evaluated by comparing the solubility of dye under various conditions.

Keywords:PMMA;azo dye;reactive dye;polymeric dye

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[1] U. S. Patent 4,710,199 (1987)

[2] U. S. Patent 6,464,733 (2002)

[3] U. S. Patent 3,954,397 (1976)

[4] U. S. Patent 5,563,260 (1996)

[5] U. S. Patent 4,245,991 (1981)

[6] U. S. Patent 6,187,888 (2001)

[7] U. S. Patent 6,417,273 (2002)

[8] U. S. Patent 5,626,633 (1997)

[9] U. S. Patent 5,800,573 (1998)

[10] U. S. Patent 5,582,621 (1996)

[11] Tentorino A, Matijevic E, Kratohvil JP, J. Colloid Interface Sci., 77, 418 (1980)

[12] Aiken B, Hsu WP, Matijevic E, J. Am. Ceram. Soc., 71, 845 (1988)

[13] Giesche and E. Matijevic E, Dyes Pigment., 17, 323 (1991)

[14] Hsu WP, Yu R, Matijevic E, Dyes Pigment., 19, 179 (1992)

[15] U. S. Patent 4,026,931 (1977)

[16] Jesionowsky T, Dyes Pigment., 55, 133 (2002)

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[18] Zhu Z, Zhu W, Dyes Pigment., 24, 281 (1994)

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[24] Sener I, Karcı F, Kılıc E, Deligoz H, Dyes Pigment., 62, 149 (2004)