Synthesis and Properties of New Soluble Polyamides Derived from 2,2‘-Dimethyl- 4,4‘-bis(4-carboxyphenoxy)biphenyl

Liaw, Der‐Jang; Liaw, Been‐Yang; Chen, Jun-Rong; Yang, Chao-Min

doi:10.1021/ma9903198

Cited by 51 publications

(49 citation statements)

References 25 publications

(45 reference statements)

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“…It is presumed that oxidation of the long-chain alkyl groups affects the thermal degradation in air, as several literature references have demonstrated that polymers with methyl and polymethylene groups show higher degradation temperatures in air than under nitrogen due to the oxidation of these groups and increase in weight. [56][57][58] On the other hand, TGA traces of polyimides based on DPABA-6, 12 showed steep weight loss at the initial stage of degradation, probably due to the degradation of three long-chain alkyl groups (Figure 7 bearing long-chain alkyl groups still can be ranked as heat resistant polymers. The solubility of the obtained polyimides was determined in 9 common solvents at 5 wt % concentration (Table III).…”

Section: Polymer Propertiesmentioning

confidence: 99%

Soluble Polyimides Based on Long-chain Alkyl Groups via Amide Linkages

Tsuda

Kojima

Matsuda

et al. 2008

Polym J

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The synthesis and characterization of a novel series of soluble polyimides bearing long-chain alkyl groups on their side chains using aromatic diamine monomers such as N-alkyl-3,5-diaminobenzamide (ADBA-X, X = carbon numbers of alkyl chain, 9$14) and N-(3,5-diaminophenyl)-3,4,5-tris(alkoxy)benzamide (DPABA-X, X = 6,12) are described. Polyimides obtained from 3,3 0 ,4,4 0 -benzophenonetetracarboxylic dianhydride (BTDA) and ADBA-9$14 were insoluble, however, copolyimides based on BTDA, ADBA-9$14, and 4,4 0 -diaminodiphenylether (DDE) were soluble. The solubility of these copolyimides may be improved by the entropy effect of long-chain linear alkyl groups as well as the randomizing effect based on copolymerization. The effect of ADBA for the enhancement of solubility was compared with a series of functional diamines bearing long-chain alkyl groups via various linkage groups reported from our laboratory such as alkoxydiaminobenzene (AODB, ether linkage), alkyldiaminobenzophenone (ADBP, benzoyl linkage) and diaminobenzoic acid alkylester (DBAE, ester linkage), and it is concluded that the effect of functional diamines are increased as AODB (ether linkage) > ADBP (benzoyl linkage) > ADBA (amide linkage) > DBAE (ester linkage). The polyimides and copolyimides based on BTDA, DPABA-6 or DPABA-12, and DDE containing 50 mol % or more DPABA were soluble, showing that the effect of DPABA for the enhancement of solubility was larger than ADBA. It is speculated that the three long-chain alkyl groups in DPABA enhance the solubility of polyimides. Above polyimides and copolyimides were soluble in various polar solvents and exhibited good heat-resistance.

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Section: Polymer Propertiesmentioning

confidence: 99%

Soluble Polyimides Based on Long-chain Alkyl Groups via Amide Linkages

Tsuda

Kojima

Matsuda

et al. 2008

Polym J

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“…2,2 -Dimethyl-4,-4 -bis(4-carboxyphenoxy)biphenyl (DA5) and 8,8-bis-[4-(4-carboxyphenoxy)phenyl]tricyclo[5.2.1.0 2,6 ]decane (DA6) were synthesized according to the procedure reported in the studies. 17,18 N, N-Dimethylformamide (DMF), N, N-dimethylacetamide (DMAc) and pyridine were purified by distillation under reduced pressure before used. Acetic anhydride was purified by vacuum distillation.…”

Section: Methodsmentioning

confidence: 99%

“…The higher T d10 value in air may reflect the oxidation of methyl groups in polymer backbone, which forms carbonyl (C=O) groups and then causes weight gain. 17,[21][22][23] The tensile properties of the polyamide films obtained by the solution-casting are also summarized in Table II. These polymer films had tensile strength of 83-113 MPa, elongation at break of 9-12%, and initial modulus of 1.7-2.1 GPa.…”

Section: Polymer Characterizationmentioning

confidence: 99%

Synthesis and Characterization of New Highly Soluble Polyamides Derived from α, α’-Bis[3,5-dimethyl-4-(4-aminophenoxy)phenyl]-1,4-Diisopropylbenzene

Liaw

Huang

Hsu

et al. 2002

Polym J

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ABSTRACT:The five benzene rings-containing diamine, α, α -bis [3,5-dimethyl-4-(4-aminophenoxy)phenyl]-1,4-diisopropylbenzene (BDAPD) was prepared by the aromatic nucleophilic substitution of α, α -bis(4-hydroxy-3,5-dimethylphenyl)-1,4-diisopropylbenzene with 1-chloro-4-nitrobenzene, and subsequent hydrogenation of the intermediate dinitro compound. The diamine was reacted with various aromatic dicarboxylic acids to prepare a series of new polyamides. The polyamides were produced with high yield and inherent viscosities of 0.68-0.94 dL g −1 . The wideangle X-Ray diffraction diagrams revealed that all the polyamides showed amorphous character. All of the polyamides showed excellent solubility in a variety of solvents such as N, N, Ndimethylformade, dimethyl sulfoxide, pyridine, cyclohexanone, and tetrahydrofuran. These five benzene ringscontaining polyamides had better solubility than those containing only one isopropylidene unit or a hexafluoroisopropylidene linkage in the repeating unit of polyamide backbone. These polyamides had glass transition temperatures (T g 's) between 237-256 • C. The thermogravimetric analyses demonstrated that almost all of the polymers were stable up to 400• C, and the 10% weight loss temperatures were recorded in the range 437-452• C and 447-463• C in nitrogen and air atmosphere, respectively.Aromatic polyamides have already been reported for their high temperature resistance and excellent mechanical properties. 1, 2 However, wholly aromatic polyamides, particularly those with para substituted rings, are quite intractable materials that do not melt and only dissolve in strong mineral acids such as concentrated sulfuric acid or in very polar aprotic solvents containing salts. Therefore, many efforts have been made to chemically modify the structure of these polymers with the aim of improving their solubility and/or lowering their transition temperatures to a range which facilitates their processing in melt.Approaches investigated in attempting to improve the solubility of polyamides include the addition of pendent groups to the polymeric backbone 3-5 and the incorporation of bulky substituents 6-9 or flexible units 10, 11 within the parent chain.A successful approach to improve the processability of aromatic polyamide without extreme loss of their outstanding properties is to introduce flexible ether and isopropylidene units into the polymer backbone. Such flexible polyamides are known to exhibit reasonable thermal stability and good mechanical properties together with excellent moldabiltiy. Our previous works observed that the solubility of polyamides, 12 polyimides, 13 and polyamide-imides 14, 15 was enhanced by incorporating the ether and isopropylidene units into the polymer backbone while retaining a satisfying thermal stability.In this study the diamine, α, α -bis [3,5-dimethyl-4-(4-aminophenoxy)phenyl]-1,4-diisopropylbenzene (BDAPD) containing flexible ether and isopropylidene units, and five benzene rings was synthesized and used to prepare a series of polyamides. Due to the...

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“…The higher Td10 in air may reflect oxidation of alicyclic norbornyl groups, to form carbonyl groups, and cause weight gain. 19 Adamantane-containing polymer P A 3 showed the highest Td10 since adamantane is generally recognized as a highly thermally stable unit. 9 Table II, it shows PA 3 to exhibit higher Td10 than Ref2.…”

Section: Polymer Characterizationmentioning

confidence: 97%

“…The amorphous behavior of the cardo polyamides was attributed to bulky pendent groups which increased significantly disorder in polymer chains and therefore caused less chain packing.The norbornyl group decreased intermolecular force such as hydrogen bonding between polymer chains, causing decrease in crystallinity. 19 Solubility of all polyamides is summarized in Thermal properties of the polyamides are summarized in Table III. All polymers displayed distinct glass transition with the second heating of DSC traces, whereas endotherms or exotherms were completely lacking. These polyamides had glass transition temperatures (Tgs) of 231-266°C.…”

Section: Polymer Characterizationmentioning

confidence: 99%

Synthesis and Properties of New Soluble Polyamides Derived from 2,2‘-Dimethyl- 4,4‘-bis(4-carboxyphenoxy)biphenyl

Cited by 51 publications

References 25 publications

Soluble Polyimides Based on Long-chain Alkyl Groups via Amide Linkages

Soluble Polyimides Based on Long-chain Alkyl Groups via Amide Linkages

Synthesis and Characterization of New Highly Soluble Polyamides Derived from α, α’-Bis[3,5-dimethyl-4-(4-aminophenoxy)phenyl]-1,4-Diisopropylbenzene

Synthesis and Characterization of New Soluble Cardo Polyamides Derived from 2,2-Bis[4-(4-carboxyphenoxy)phenyl]norbornane

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