New fluorinated aromatic poly(ether-amide)s derived from 2,2′-bis(3,4,5-trifluorophenyl)-4,4′-diaminodiphenyl ether and various dicarboxylic acids (original) (raw)
Related papers
Colloid & Polymer Science, 2006
Syntheses and properties of fluorinated polyamides and poly(amide imide)s based on 9,9-bis[4-(4-amino-2-trifluromethylphenoxy) phenyl]fluroene, aromatic dicarboxylic acids, and various monotrimellitimides and bistrimellitimides Abstract A diamine, 9,9-bis[4-(4amino-2-trifluromethylphenoxy)phenyl]fluroene (I) containing the CF 3 group, was prepared from 9,9-bis (4-hydroxyphenyl)fluorene and 2-chloro-5-nitrobenzotrifluoride. The imide-containing diacids (V a-j and VI a,b) were prepared by condensation reaction of amino acids, aromatic diamines, and trimellitic anhydride. Then, a series of soluble fluorinated polyamides (VII a-e) and poly(amide imide)s (VIII a-j and X a,b) were synthesized from diamine (I) with various aromatic diacids II a-h and the imide-containing diacids (V a-j and VI a,b) via direct polycondensation with triphenyl phosphate and pyridine. All polymers showed excellent solubility in amide-type solvents such as N-dimethylforamide and can also be dissolved in pyridine, m-cresol, and tetrahydrofuran. Polymers afford transparent and tough films by solvent casting. The glass transition temperature of these polymers were in the range of 278-366°C, and the poly(amide imide)s had better thermal stability than polyamides. In comparison with the isomeric IX ad , VIII ad showed a lighter color with lower b* (yellowness index) values than the corresponding IX series. Keywords 9,9-bis[4-(4-amino 2-trifluromethylphenoxy)phenyl] fluroene. Fluorinated polyamides. Fluorinated poly(amide imide)s. Aromatic dicarboxylic acids
Colloid and Polymer Science, 2006
Syntheses and properties of fluorinated polyamides and poly(amide imide)s based on 9,9-bis[4-(4-amino-2-trifluromethylphenoxy) phenyl]fluroene, aromatic dicarboxylic acids, and various monotrimellitimides and bistrimellitimides Abstract A diamine, 9,9-bis[4-(4amino-2-trifluromethylphenoxy)phenyl]fluroene (I) containing the CF 3 group, was prepared from 9,9-bis (4-hydroxyphenyl)fluorene and 2-chloro-5-nitrobenzotrifluoride. The imide-containing diacids (V a-j and VI a,b) were prepared by condensation reaction of amino acids, aromatic diamines, and trimellitic anhydride. Then, a series of soluble fluorinated polyamides (VII a-e) and poly(amide imide)s (VIII a-j and X a,b) were synthesized from diamine (I) with various aromatic diacids II a-h and the imide-containing diacids (V a-j and VI a,b) via direct polycondensation with triphenyl phosphate and pyridine. All polymers showed excellent solubility in amide-type solvents such as N-dimethylforamide and can also be dissolved in pyridine, m-cresol, and tetrahydrofuran. Polymers afford transparent and tough films by solvent casting. The glass transition temperature of these polymers were in the range of 278-366°C, and the poly(amide imide)s had better thermal stability than polyamides. In comparison with the isomeric IX ad , VIII ad showed a lighter color with lower b* (yellowness index) values than the corresponding IX series. Keywords 9,9-bis[4-(4-amino 2-trifluromethylphenoxy)phenyl] fluroene. Fluorinated polyamides. Fluorinated poly(amide imide)s. Aromatic dicarboxylic acids
Journal of Applied Polymer Science, 2006
A CF 3-containing diamine, 4,4 0-bis(4-amino-2-trifluoromethylphenoxy)benzophenone (2), was synthesized from 4,4 0-dihydroxybenzophenone and 2-chloro-5nitrobenzotrifluoride. Imide-containing diacids (3 and 5B a-5B g) were prepared by the condensation reaction of aromatic diamines and trimellitic anhydride. Then, two series of novel soluble aromatic poly(amide imide)s (PAIs; 6A a-6A k and 6B a-6B g) were synthesized from a diamine (4A a-4A k or 2) with the imide-containing diacids (3 and 5B a-5B g) via direct polycondensation with triphenyl phosphate and pyridine. The aromatic PAIs had inherent viscosities of 0.74-1.76 dL/g. All of the synthesized polymers showed excellent solubility in amide-type solvents, such as N-methyl-2-pyrrolidone and N,N-dimethylacetamide (DMAc), and afforded transparent and tough films by DMAc solvent casting. These polymer films had tensile strengths of 90-113 MPa, elongations at break of 8-15%, and initial moduli of 2.0-2.9 GPa. The glasstransition temperatures of the aromatic PAIs were in the range 242-2798C. They had 10% weight losses at temperatures above 5008C and showed excellent thermal stabilities. The 6B series exhibited less coloring and showed lower yellowness index values than the corresponding 6A series.
Polymer, 2003
A novel aromatic diamine, 1,1-bis(4-amino-3,5-dimethylphenyl)-1-(3,4,5-trifluorophenyl)-2,2,2-trifluoroethane, containing a pendant polyfluorinated phenyl group, a trifluoromethyl group, and methyl groups orthosubstituted to the amino groups in the structure was synthesized and characterized. The diamine was polymerized with several aromatic dianhydrides, including 3,3 0 ,4,4 0biphenyltetracarboxylic dianhydride, 3,3 0 ,4,4 0 -benzophenonetetracarboxylic dianhydride, 4,4 0 -oxydiphthalic anhydride, and 4,4 0 -hexafluoroisopropylidene diphthalic anhydride, via a high-temperature one-step procedure to afford four polyimides (PIs) with inherent viscosities of 0.47-0.70 dL/g. The PIs exhibited excellent solubilities in a variety of organic solvents. They were soluble not only in polar aprotic solvents but in many common solvents, such as cyclopentanone, tetrahydrofuran, and even toluene at room temperature. The tough and flexible PI films cast from the PI solutions exhibited good thermal stabilities and acceptable tensile properties. The glass-transition temperatures were in the range 312-365 C, and the 5% weight loss temperatures were all higher than 480 C in nitrogen. The films had tensile strengths in the range 76-99 MPa, tensile moduli of 2.2-2.8 GPa, and elongations at break of 5-8%. In addition, the PI films exhibited excellent transparency in the visible light region with cutoff wavelength as low as 302 nm and transmittance higher than 88% at the wavelength of 450 nm. The PI films showed low dielectric constants ranging from 2.50-2.68 and low moisture absorptions of less than 0.56%. The good combined properties of the PIs mainly resulted from the synergic effects of the different substituents. V
Journal of Applied Polymer Science, 2009
A novel aromatic diamine, 1,1-bis(4-amino-3,5-dimethylphenyl)-1-(3,4,5-trifluorophenyl)-2,2,2-trifluoroethane, containing a pendant polyfluorinated phenyl group, a trifluoromethyl group, and methyl groups orthosubstituted to the amino groups in the structure was synthesized and characterized. The diamine was polymerized with several aromatic dianhydrides, including 3,3 0 ,4,4 0biphenyltetracarboxylic dianhydride, 3,3 0 ,4,4 0 -benzophenonetetracarboxylic dianhydride, 4,4 0 -oxydiphthalic anhydride, and 4,4 0 -hexafluoroisopropylidene diphthalic anhydride, via a high-temperature one-step procedure to afford four polyimides (PIs) with inherent viscosities of 0.47-0.70 dL/g. The PIs exhibited excellent solubilities in a variety of organic solvents. They were soluble not only in polar aprotic solvents but in many common solvents, such as cyclopentanone, tetrahydrofuran, and even toluene at room temperature. The tough and flexible PI films cast from the PI solutions exhibited good thermal stabilities and acceptable tensile properties. The glass-transition temperatures were in the range 312-365 C, and the 5% weight loss temperatures were all higher than 480 C in nitrogen. The films had tensile strengths in the range 76-99 MPa, tensile moduli of 2.2-2.8 GPa, and elongations at break of 5-8%. In addition, the PI films exhibited excellent transparency in the visible light region with cutoff wavelength as low as 302 nm and transmittance higher than 88% at the wavelength of 450 nm. The PI films showed low dielectric constants ranging from 2.50-2.68 and low moisture absorptions of less than 0.56%. The good combined properties of the PIs mainly resulted from the synergic effects of the different substituents. V
Journal of Polymer Science Part A: Polymer Chemistry, 2004
A CF 3-containing diamine, 1,4-bis(4-amino-2-trifluromethylphenoxy) benzene (I), was prepared from hydroquinone and 2-chloro-5-nitrobenzotrifluoride. Imidecontaining diacids (V a-h and VI a,b) were prepared through the condensation reaction of amino acids, aromatic diamines, and trimellitic anhydride. Then, a series of soluble fluorinated polyamides (VII a-h) and poly(amide imide)s (VIII a-h and X a,b) were synthesized from I with various aromatic diacids (II a-h) and imide-containing diacids (V a-h and VI a,b) via direct polycondensation with triphenyl phosphate and pyridine. The polyamides and poly(amide imide)s had inherent viscosities of 1.00-1.70 and 0.79-1.34 dL/g, respectively. All the synthesized polymers showed excellent solubility in amide-type solvents such as N-methyl-2-pyrrolidinone, N,N-dimethylacetamide, and N-dimethylformamide and afforded transparent and tough films via solvent casting. Polymer films of VII a-h , VIII a-h , and X a,b had tensile strengths of 91-113 MPa, elongations to break of 8-40%, and initial moduli of 2.1-2.8 GPa. The glass-transition temperatures of the polyamides and poly(amide imide)s were 254-276 and 255-292°C, respectively, and the imide-containing poly(amide imide)s had better thermal stability than the polyamides. The polyamides showed higher transparency and were much lighter in color than the poly(amide imide)s, and their cutoff wave numbers were below 400 nm. In comparison with isomeric IX c-h , poly(amide imide)s VIII c-h exhibited less coloring and showed lower yellowness indices.