Synthesis and Characterization of New Comb-Like Polyguanamines Containing Three Long Alkyl Side-Chains in Repeating Unit

Abstract

ABSTRACT:Novel comb-like poly(amide-guanamine)s, poly(urea-guanamine)s and poly-(imide-guanamine)s which contain three long alkyl side-chains in each repeating unit (three sidechains polymers), were synthesized by the reaction of 2,4-bis(amino-N-octadecylanilino)-6-heptadecyl-l,3,5-triazines with aromatic or aliphatic diacid chlorides, diisocyanates and pyromellitic dianhydride, respectively. Making reference to the three side-chain polymers, the corresponding one side-chain polymers were also prepared using 2,4-bis(aminoanilino)-6-heptadecyl-1,3,5-triazine as a monomer. Although the one side-chain polymers were insoluble in tetrahydrofuran, chloroform, toluene and benzene, the three side-chains polymers except polyimides were readily soluble in these solvents. These polymers had good thermal stability though the bulky long alkyl groups were present. The three side-chains polymers are characterized by side-chain crystallinity. The one side-chain polymers were found to show low crystallinity by differential scanning calorimetry and wide angle X-ray diffraction. The influence of the main-chain structure on the sidechain crystallization was investigated.KEY WORDS Comb-Like Polymer/ 1,3,5-Triazine / Long Alkyl Group/ Poly(amide-guanamine) / Poly(urea-guanamine) / Poly(imide-guanamine) / Side-Chain Crystallization / Comb-like polymers containing rigid mainchain and flexible long alkyl side-chains have attracted great interest because this specific combination is expected to lead to a favorable property. 1 -5 For example, N-octadecylated poly(p-phenylene terephthalamide) containing the rigid backbone and flexible alkyl sidechains shows side-chain crystallization and liquid crystalline behavior of the lyotropic type. For dynamic mechanical properties, two characteristic relaxations were observed, and assigned to the crystalline and amorphous phase of the side-chains, respectively. 3 In previous papers of this series 6 -9 we investigated the properties of several aromatic comb-like polymers prepared from diamines containing 1,3,5-triazine ring with one (1 6 ) or two long alkyl groups (II, 7 111 8 and IV 9 ). II 92Polym.

Polymers grafted to convex surfaces: a variational approach

“…These typically have short alkane side branches attached to an organic backbone. 21 The main observed impact of the stretching of these side chains is on the induced stiffness in the comb p~l y m e r .~~*~~ We have seen no evidence regarding the exclusion zone in these polymers. Similar exclusion zones should occur in cylindrical block-copolymer micelles.24 In addition, the density and pressure at the periphery of such brushes are qualitatively weaker in our exact solution and in our approximations than in the simpler step-function profiles considered previously.…”

“…These typically have short alkane side branches attached to an organic backbone. 21 The main observed impact of the stretching of these side chains is on the induced stiffness in the comb polymer.22 •23 We have seen no evidence regarding the exclusion zone in these polymers. Similar exclusion zones should occur in cylindrical block-copolymer micelles.…”

Synthesis of highly refractive and highly fluorescent rigid cyanuryl polyimines with polycyclic aromatic hydrocarbon pendants

“…Polyguanamines (PGs) are a family of polyimines easily accessible through conventional solution polycondensation, and can be readily modified using 2-substituted 4,6-dichloro-1,3,5triazine (DCT) as the monomer. [1][2][3][4][5][6][7][8][9] PG polymers have melamine units that can act as both hydrogen bond donors and acceptors, resulting in the formation of various types of useful supramolecules. [10][11][12][13][14][15][16] We previously reported the chemoselective polycondensation of 2-amino-4,6-dichlorotriazine (ADCT) with 4,4′-(9-fluorenylidene)dianiline (BAFL), where the amino functional group on the ADCT monomer was nearly inert during polymerization, in a chemoselective manner.…”

The role of intramolecular and intermolecular hydrogen bonding effect for adenine-containing polyimide films

“…[4][5][6][7] In order to improve thermal and mechanical properties, triazine ring and imidazole-containing polyimides were synthesized. [8][9][10] In many researches, the introduction of aromatic heterocyclic moiety into polyimide is an effective approach to enhance the properties of polyimides. For example, the soluble pyridine-containing polyimides have been prepared by Zhao et al 11 The mechanical properties of polyimide fiber were enhanced by introducing a benzoxazole unit.…”