Synthesis and characterization of linear, hyperbranched and dendritic poly(arylene ether amide)s through nitro displacement reaction = 나이트로 치환 반응을 이용한 아릴 에테르 아미드계 선형, 하이퍼브랜치 고분자 및 덴드리머의 합성과 특성에 관한 연구

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Novel AB type monomers with one amide linkage, 4-nitro-3-trifluoromethyl-N-(4-hydroxyphenyl)benzamide (3) and 4-nitro-3-trifluoromethyl-N-(3-hydroxyphenyl)-benzamide (4) were synthesized and self-polymerized using nitro displacement reaction in the presence of potassium carbonate in DMSO. The synthesized polyamides showed the enhanced solubility without deterioration of thermal property. Four AB type monomers with two amide linkages, N-[4-(4-nitro-3-trifluoromethylbenzamido)]-N``(4-hydroxyphenyl)benzamide (7), N-[4-(4-nitro-3-trifluoromethylbenzamido)]-N``(3-hydroxyphenyl)benzamide (8), N-[3-(4-nitro-3-trifluoromethylbenzamido)]-N``(4-hydroxyphenyl)benzamide (9) and N-[3-(4-nitro-3-trifluoromethylbenzamido)]-N``(3-hydroxyphenyl)benzamide (10), were also synthesized and polymerized. The polyamides with two amide linkages per repeating unit were soluble in NMP and DMSO, but not in THF whereas the polyamides with one amide linkage per repeating unit were soluble in common organic solvents including THF. This solubility result indicates that the number of amide linkages is an important factor to control the solubility of aromatic polyamides. A series of AABB type poly(arylene ether amide)s having weight average molecular weight of 30,000 - 70,000 were prepared from N,N``-bis(4-nitro-3-trifluoromethylbenzoyl)-p-phenylenediamine (16) and N,N``-bis(4-nitro-3-trifluoromethylbenzoyl)-m-phenylenediamine (17) and several biphenol compounds. All the synthesized polyamides showed high glass transition temperature values above 213℃ and good solubility. Novel $AB_2$ type monomer containing one amide linkage, N-(3,5-dihydroxyphenyl)-4-nitro-3-trifluoromethyl-benzamide (20) was synthesized and polymerized under various conditions using nitro displacement reaction to produce hyperbranched poly(arylene ether amide)s. The synthesized hyperbranched poly(arylene ether amide)s are highly soluble in common organic solvents and their weight average molecular weights were in the range...
Advisors
Kim, Sang-Youlresearcher김상율researcher
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
2002
Identifier
177227/325007 / 000985308
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 2002.8, [ xiii, 196 p. ]

Keywords

dendrimers; hyperbranched polymers; poly(arylene ether amide)s; nitro displacement reaction; trifluoromethyl group; 트리플루오르메틸기; 덴드리머; 하이퍼브랜치 고분자; 아릴 에테르 아미드계 고분자; 나이트로 치환 반응

URI
http://hdl.handle.net/10203/31588
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=177227&flag=dissertation
Appears in Collection
CH-Theses_Ph.D.(박사논문)
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