Synthesis and characterization of norbornane‐containing cardo polyamides

Liaw, Der‐Jang; Liaw, Been‐Yang

doi:10.1002/(sici)1099-0518(19990801)37:15<2791::aid-pola13>3.0.co;2-#

Cited by 24 publications

(18 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[4] One of the approaches successfully used with those purposes is the incorporation of monomers with bulky side (pendent) groups. [5][6][7][8] The presence of side, bulky groups prevents an efficient molecular packing, and restricts the formation of interchain hydrogen bonds, which are responsible of the APA's intractability. Previous results in this line have proved that a sound choosing of chemical elements can help for preparing novel APA's that show improved properties, as they can be dissolved by organic solvents and, at the same time, they maintain the thermal resistance of the conventional APA's in great extent.…”

Section: Introductionmentioning

confidence: 99%

Thermal and Mechanical Properties of Halogen-Containing Aromatic Polyamides

Álvarez

Campa

Lozano

et al. 2001

Macromol. Chem. Phys.

View full text Add to dashboard Cite

Aromatic polyamides containing fluorine, chlorine, bromine and iodine have been prepared, and they have been evaluated by their mechanical and thermal properties. The method of polycondensation in solution at low temperature revealed as a very appropriate route to attain high molecular‐weight halogen‐containing polyisophthalamides (PIPA's) from aromatic diamines and 5‐halogenoisophthaloyl chlorides. High glass transition temperatures (Tg) were found for the set of polymers, in the range 250–350°C, showing a clear dependence on the size of the halogen incorporated, with values of Tg growing up in the series F < Cl < Br < I. On the other hand, thermal resistance was slightly impaired by the presence of halogens, as revealed by thermogravimetric analysis (TGA). In the same way, the mechanical strength was poorer than that of the parent unmodified PIPA's, by about 20%. All the polymers exhibited a mechanical relaxation at sub‐ambient temperature, about –70°C, associated to local molecular motions involving halogen atoms.

show abstract

Section: Introductionmentioning

confidence: 99%

Thermal and Mechanical Properties of Halogen-Containing Aromatic Polyamides

Álvarez

Campa

Lozano

et al. 2001

Macromol. Chem. Phys.

View full text Add to dashboard Cite

show abstract

“…The introduction of cardo groups along the polymer backbone has been shown to impart greater solubility, enhanced rigidity, and better mechanical and thermal properties 17. It has been reported that the presence of cardo groups such as fluorene,18, 19 phthalide,20 phthalimidine,21, 22 cyclododecylidene,23 adamantine,24 tricyclo [5.2.1.02, 6]decane,25 norbornane26 and tert ‐butylcyclohexylidene27 groups into the backbone of polyamides yields polymers with enhanced solubility, processability, and good thermal stability. Although many excellent polyamides are known and commercially available, new polyamides are continuing to appear as researchers continue to conduct fundamental studies on chemical structure/property relationships.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of novel aromatic polyamides with xanthene cardo groups

Sheng

Jiang

et al. 2010

J of Applied Polymer Sci

View full text Add to dashboard Cite

Two novel monomers, 9,9-bis[4-(4-carboxyphenoxy)phenyl]xanthene (BCAPX) and 9,9-bis[4-(4-aminophenoxy)phenyl]xanthene (BAPX) were prepared in two main steps starting from nucleophilic substitution of 9,9-bis(4-hydroxyphenyl)xanthene (BHPX) with p-fluorobenzonitrile and p-chloronitrobenzene, respectively. Using triphenyl phosphite and pyridine as condensing agents, two series of polyamides containing xanthene cardo groups with the inherent viscosities (0.82-1.32 dL/g) were prepared by polycondensation from BCAPX with various aromatic diamines or from BAPX with various aromatic dicarboxylic acids in an N-methyl-2-pyrrolidone (NMP) solution containing dissolved calcium chloride, respectively. All new polyamides were amorphous and readily soluble in various polar solvents such as N,N-dimethylformamide (DMF), NMP, N,N-dimethylacetamide (DMAc) and pyridine. These polymers showed relatively high glass transition temperatures between 264 and 308 C, decomposition temperatures at 10% weight loss ranging from 502 to 540 C and 488 to 515 C in nitrogen and air, respectively, and char yields at 800 C in nitrogen higher than 56%. Transparent, flexible, and tough films of these polymers cast from DMAc solutions exhibited tensile strengths ranging from 86 to 109 MPa, elongations at break from 13 to 22%, and initial moduli from 2.15 to 2.63 GPa.

show abstract

“…Introducing pendent loops into the polymer backbone is a successful approach for improving the processability of aromatic polyamide without an extreme loss of their outstanding properties 9. It has been reported that incorporating cardo groups such as fluorene,10 phthalide,11 phthalimidine,12 cyclododecylidene,13 adamantine,14 tricyclo [5.2.1.0 2,6 ]decane,15 norbornane,16 and tert ‐butylcyclohexylidene17 groups into the backbone of polyamides provides polymers with greater solubility, enhanced rigidity, and better mechanical and thermal properties. Furthermore, it is well known that the incorporation of trifluoromethyl substituents into polymers reduces the dielectric constant because of the low‐electronic polarizability of the CF bond and the increase in the fractional free volume 4, 18–24.…”

Section: Introductionmentioning

confidence: 99%

High‐optical transparency and low‐dielectric constant of new organosoluble polyamides containing trifluoromethyl and xanthene groups

Sheng

Wei

et al. 2010

J of Applied Polymer Sci

View full text Add to dashboard Cite

A series of fluorinated polyamides was prepared directly by low-temperature polycondensation of a new cardo diacid chloride, 9,9-bis[4-(4-chloroformylphenoxy)phenyl]xanthene (BCPX), with various diamines containing trifluoromethyl substituents in N,N-dimethylacetamide (DMAc). Almost all polyamides showed excellent solubility in amide-type solvents such as DMAc and could also be dissolved in pyridine, m-cresol, and tetrahydrofuran. These polymers had inherent viscosities between 0.77 and 1.31 dL g À1, and their weight-average molecular weights and number-average molecular weights were in the range of 69,000-102,000 and 41,000-59,000, respectively. The resulting polymers showed glass transition temperatures between 240-258 C and 10% weight loss temperatures ranging from 484 C to 517 C and 410 C to 456 C in nitrogen and air, respectively, and char yields at 800 C in nitrogen higher than 55%. All polymers were amorphous and could be cast into transparent, light-colored, and flexible films with tensile strengths of 81-100 MPa, elongations at break of 8-12%, and tensile modulus of 1.6-2.1 GPa. These polymers had low-dielectric constants of 3.34-3.65 (100 kHz), low-moisture absorption in the range of 0.76-1.91%, and high transparency with an ultraviolet-visible absorption cut-off wavelength in the 322-340 nm range.

show abstract

Synthesis and characterization of norbornane‐containing cardo polyamides

Cited by 24 publications

References 19 publications

Thermal and Mechanical Properties of Halogen-Containing Aromatic Polyamides

Thermal and Mechanical Properties of Halogen-Containing Aromatic Polyamides

Synthesis and properties of novel aromatic polyamides with xanthene cardo groups

High‐optical transparency and low‐dielectric constant of new organosoluble polyamides containing trifluoromethyl and xanthene groups

Contact Info

Product

Resources

About