Photodeprotectable N-Alkoxybenzyl Aromatic Polyamides

Abstract

N-alkoxybenzyl aromatic polyamides were synthesized by polycondensation of N-alkoxybenzyl aromatic diamine with equimolar dicarboxylic acid chloride in the presence of 2.2 equiv. of pyridine at room temperature for 2 days. The obtained polyamides were mainly cyclic polymers, as determined by means of matrix-assisted laser desorption ionization time-of-flight (MALDI-TOF) mass spectrometry, and showed higher solubility in organic solvents than unprotected aromatic polyamides. Photodeprotection of N-alkoxybenzyl aromatic polyamide film containing photo acid generator (PAG) proceeded well under UV irradiation (5 J/cm 2 ), followed by heating at 130 • C for 15 min. The nature of the polymer end groups of N-alkoxybenzyl aromatic polyamides was found to be crucial for photodeprotection reactivity. These polymers are promising candidates for photosensitive heat-resistant materials for fine Cu wiring formation by electroless Cu plating of high-density semiconductor packaging substrates.

Chain‐growth polycondensation via the substituent effect: Investigation of the monomer structure on synthesis of poly(N‐octyl‐benzamide)

“…The clear majority of literature on application of the CGC technique involves the polymerization of methyl ester monomers (1a), which have proved to be mostly successful in producing defined polymers and also produces lowboiling point byroducts. [14][15][16][25][26][27][28][29][30][31][32] Based on this literature, we hypothesized that the methyl monomer would be a good candidate for the preparation of aromatic polyamide brushes via CGC polymerization in our original work. [11] However, in this work it was observed that control over the polymerization was only achieved up to a degree of polymerization (DP) of 80, which also corresponds to literature studying solution polymerizations of the same monomer.…”

Non-stoichiometric effect in the superacid-catalyzed polyhydroxyalkylation of biphenyl and 1-propyl isatin

“…This technique has recently been shown to be relevant in the identification of macrocycles. 36–38 The MALDI-TOF spectrum for the LMWR at 8 h is shown in Figure 9. The MALDI-TOF spectra for 2–7 h were very similar to the one at 8 h. The MALDI-TOF spectrum for the LMWR at 8 h, plotted together with the full molecular weight distribution (MWD) considering both regions, LMWR and HMWR, at the same time, are shown in Figure 10.…”

“…This technique has recently been shown to be relevant in the identification of macrocycles. [36][37][38] The MALDI-TOF spectrum for the LMWR at 8 h is shown in Figure 9. The MALDI-TOF spectra for 2-7 h were very The classical theory of A 2 + B 2 (CTA2B2) SGP postulates equal reactivity of polymer molecules, regardless of their size.…”

Novel Photoresist using Photodeprotectable <i>N</i>-Alkoxybenzyl Aromatic Polyamide

“…In other words, the photosensitive N-alkoxybenzyl aromatic polyamide would be converted to aromatic polyamide having a high adhesion property by means of UV-irradiation. In the previous report, we have demonstrated that highly soluble N-alkoxybenzyl aromatic polyamides were converted to N-H polyamides with low solubility through photodeprotection of the alkoxybenzyl group with PAG [22]. Photodeprotection of N-alkoxybenzyl aromatic polyamides with PAG proceeded under 5 J/cm 2 of UV irradiation, followed by heating at 130 o C for 15 min afforded the corresponding N-H polyamides (Scheme 1).…”