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Multivalent photo-crosslinkable coumarin-containing polybenzoxazines exhibiting enhanced thermal and hydrophobic surface properties

机译:含有多价光可交联的香豆素的聚苯细胞,具有增强的热和疏水性表面性能

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摘要

In this study, mono-, bi-, and trivalent coumarin-containing benzoxazine monomers (mono-, di-, and tri-coumarin BZ) were synthesized in high yield and purity by facile Mannich reactions of 4-methyl-7-hydroxycoumarin and paraformaldehyde with aniline, bisphenol A-NH2, and 1,3,5-tri(4-aminobenzene), respectively, in 1,4-dioxane. H-1 and C-13 nuclear magnetic resonance (NMR), Fourier transform infrared (FTIR) and high resolution mass spectroscopy support the chemical structures of these three benzoxazine monomers. Differential scanning calorimetry (DSC) and FTIR spectroscopy were used to investigate the curing polymerization behavior and photodimerization ([2 pi + 2 pi] cycloaddition) of the coumarin units of mono-, di-, and tri-coumarin BZ to form poly(mono-coumarin BZ), poly(di-coumarin BZ), and poly(tri-coumarin BZ), respectively. DSC measurement revealed that the thermal polymerization temperature of coumarin-containing benzoxazine monomers was lower than that of the model compound 3-phenyl-3,4-dihydro-2H-benzooxazine (263 degrees C) which was attributed to the catalytic effect of the coumarin moiety and a strong electron withdrawing electron conjugated C=C bond in the coumarin unit. In addition, the glass transition and thermal decomposition temperatures of poly(tri-coumarin BZ) (T-g = 240 degrees C; T-d5 = 370 degrees C) were higher than poly(di-coumarin BZ) and poly(mono-coumarin BZ), consistent with the former's higher crosslinking density. In addition, the water contact angles of poly(tri-coumarin BZ) polymers prepared with and without photo-dimerization prior to thermal curing (112 and 110 degrees, respectively) were higher than the corresponding poly(mono-coumarin BZ) and poly(di-coumarin BZ), presumably because of greater degrees of intramolecular hydrogen bonding between the C=O units of the coumarin moieties and the phenolic OH units of the benzoxazine rings, resulting in lower surface free energies. Thus, the presence of multivalent photo-crosslinkable coumarin units enhanced the thermal and hydrophobic surface properties of these polybenzoxazines.
机译:在这项研究中,单环,双环,和三价含香豆素的苯并恶嗪的单体(单,二,和三 - 香豆素BZ)以高收率和纯度合成由容易4-甲基-7-羟基香豆素的曼尼希反应和具有苯胺,双酚A-NH2和1,3,5-三苯二酚的多聚甲醛,分别在1,4-二恶烷中。 H-1和C-13核磁共振(NMR),傅里叶变换红外(FTIR)和高分辨率质谱支持这三种苯并恶嗪单体的化学结构。使用差分扫描量热法(DSC)和FTIR光谱学研究了单,二 - 和三 - 香豆素BZ的香豆素单位的固化聚合行为和光电二聚体([2 pi + 2 pi]环加成)以形成聚(单声道-coumarin bz),聚(Di-CoMarin BZ)和聚(三豆素BZ)。 DSC测量揭示含香豆素的苯并恶嗪单体的热聚合温度比模型化合物3-苯基-3,4-二氢-2H-苯并恶嗪的低级(263摄氏度),将其归因于香豆素的催化作用部分和强电子取出电子共轭C = C键在香豆素单位中。此外,聚(Tri-Coumarin Bz)(Tg = 240℃; T-D5 = 370℃)的玻璃化转变和热分解温度高于聚(Di-Cofarin BZ)和聚(单对香豆素BZ ),与前者更高的交联密度一致。此外,在热固化之前用且没有光二聚化(分别在热固化(112和110度)之前制备的聚(三豆蛋白BZ)聚合物的水接触角(112和110度)高于相应的聚(单对香豆素BZ)和聚(据推测,Di-CoMarin BZ),由于香豆素部分的C = O单元和苯并恶嗪环的酚类OH单元之间的细胞分子内氢键合更大的分子内氢键,导致较低的无表面自由能量。因此,多价光交联香豆素单元的存在增强了这些聚苯并嗪的热和疏水表面性质。

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  • 来源
    《RSC Advances》 |2016年第13期|共14页
  • 作者单位

    Natl Sun Yat Sen Univ Dept Mat &

    Optoelect Sci Kaohsiung 80424 Taiwan;

    Natl Sun Yat Sen Univ Dept Mat &

    Optoelect Sci Kaohsiung 80424 Taiwan;

    Natl Sun Yat Sen Univ Dept Mat &

    Optoelect Sci Kaohsiung 80424 Taiwan;

    Natl Sun Yat Sen Univ Dept Mat &

    Optoelect Sci Kaohsiung 80424 Taiwan;

    Natl Sun Yat Sen Univ Dept Mat &

    Optoelect Sci Kaohsiung 80424 Taiwan;

    Natl Sun Yat Sen Univ Dept Mat &

    Optoelect Sci Kaohsiung 80424 Taiwan;

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 化学;
  • 关键词

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