Preparation and properties of novel soluble aromatic polyetherimides from 1,1′-bis[4-(3,4-dicarboxyphenoxy) phenyl]-1-phenyl-2,2,2-trifluoroethane dianhydride and aromatic diamines

Ahn

Macro Chemistry & Physics

2004

Summary: We describe the synthesis and characterization of a soluble photoreactive polyimide. The precursor of the polyimide was prepared from 2,2′‐bis{4‐(3,4‐dicarboxyphenoxy)phenyl}hexafluoropropane dianhydride and 3,3′‐hydroxy‐4,4′‐diaminobiphenyl; the photoreactive polyimide was then prepared by the polymer reaction of the hydroxyl groups in the precursor polymer with 2‐{2‐[4‐(6‐hydroxyhexyloxy)phenyl]ethenyl}pyridine as a photoreactive 2‐styrylpyridine derivative. The photoreactive polymer and its precursor polymer were soluble in various polar organic solvents, and their thin flexible films were easily formed by solution casting. The initial decomposition temperatures of the former and latter polymers were 350 and 470 °C, respectively. The extent of the photochemical reaction of the photoreactive polymer film was measured to be 65.8% at an exposure energy of 1.5 J/cm2. The transmittance of the film was found to be approximately 92% at room temperature and approximately 85% at 200 °C. These results suggest that the polyimide is a photosensitive polymer with good photosensitivity and high optical transparency. The dichroic ratios of the film were between 0.023 and 0.025 when exposed to linearly polarized UV light (LPUVL). The liquid crystal in the film cell was perpendicularly oriented to the electric vector of LPUVL.

Section: Experimental Partmentioning

confidence: 99%

Soluble Polyimide Containing a Photoreactive 2‐Styrylpyridine Derivative as the Side Group: Synthesis and Characterization

Ahn

Macro Chemistry & Physics

2004

“…A reduction of the CTC generally provides polyimides with lighter color 12, 13. In addition, one of the most effective methods of decreasing the dielectric constant is to introduce fluorine atoms into polyimide materials 14–17…”

Section: Introductionmentioning

confidence: 99%

Organosoluble and light‐colored fluorinated polyimides derived from 5,5′‐bis[4‐(4‐amino‐2‐trifluoromethylphenoxy) phenyl]‐4,7‐methanohexahydroindan

Yang

Hsu

2006

Polymer International

A novel bis(ether amine) monomer, 5,5 -bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]-4,7methanohexahydroindan (2), was synthesized through the nucleophilic aromatic substitution reaction of 5,5 -bis-(4-hydroxyphenyl)-4,7-methanohexahydroindan with 2-chloro-5-nitrobenzotrifluoride to yield the intermediate dinitro compound, followed by catalytic reduction with hydrazine and Pd/C. A series of polyimides were synthesized from 2 and various aromatic dianhydrides using a standard two-stage process with chemical or thermal imidization of poly(amic acid). All of these polymer films were soluble in amide-type solvents above 10% w/v, had tensile strengths of 97-117 MPa, and the 10% weight loss temperature was above 464 • C with their residues exceeding 46% at 800 • C in nitrogen. Compared with the non-fluorinated polyimides, the fluorinated series were observed to have lower dielectric constants (2.92-3.28 at 1 MHz) and lower moisture absorptions (0.15-0.43 wt%) as well as lower color intensity and better solubility.

Preparation and properties of soluble aromatic polyetherimides based on 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl]hexafluoropropane dianhydride

Lee

Koo

et al. 2000

J. Appl. Polym. Sci.

Self Cite

Aromatic polyetherimides were synthesized from a fluorine containing aromatic carboxylic acid dianhydride, 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl]-hexafluoropropane dianhydride (6F-BABPA) and five typical aromatic diamines including 1,1-bis(4-aminophenyl)-1-phenyl-2,2,2-trifluoroethane (3F-DAM) by two-step procedures-amidation to polyamic acids (PAA), followed by thermal imidization of PAA. The chemical and physical properties of the newly prepared polyetherimides (PEI) were compared in terms of their chemical structures, inherent viscosities, mechanical, and thermal properties. All polyetherimides were well soluble in common organic solvents such as N-methyl-2-pyrolidone (NMP), N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAc), pyridine, and methylene chloride. A PEI prepared from 6F-BABPA/3F-DAM was especially easily dissolved in NMP. The glass transition temperature (T g ) range of the obtained PEI was 209 -257°C. The dielectric constants and refractive index were 2.8 -3.2 and 1.61-1.56, respectively. The polyetherimide, 6F-BABPA/BAPP, with a low fluorine content (11.4% fluorine content), has 0.99% water absorption, whereas the polyetherimide, 6F-BABPA/4-BDAP, having a high fluorine content (26.0% fluorine content) showed 0.35% of water absorption.