Series Of Bisphenol Research Articles

A novel bisphenol A‐free polyarylates synthesis strategy: 4,4′‐sulfobisphenol/2,2‐bis(4‐hydroxyphenyl)butane co‐polyarylate prepared by interfacial polymerization

AbstractA series of bisphenols, 4,4′‐sulfobisphenol (BPS)/2,2‐bis(4‐hydroxyphenyl)butane (BPB) co‐polyarylates with amorphous structures were synthesized from two BPS and BPB, and two different structures of benzoyl chloride monomers. The results of DFT calculations showed that the reaction activation energy of BPB with isophthaloyl chloride (IPC) and terephthaloyl chloride (TPC) was 8.05–8.40 Kcal/mol. The reaction activation energy of BPS with IPC and TPC was 38.73–39.09 Kcal/mol. GPC test results were consistent with theoretical calculations with BPS content from 0% to 15% resulting in a copolymer Mn of 22,000–11,600 and a Mw of 46,100–34,800. The intrinsic viscosity of co‐polyarylates ranged from 0.55 to 0.71 dL/g. The glass transition temperature (Tg) and 5% thermal weight loss of the co‐polyarylates were 179.3–205.4 °C and 461.4–487.8 °C, respectively. Improved solubility of co‐polyarylates in polar solvents. At the same time, the introduction of BPS did not result in any loss of mechanical properties, with Young's modulus in the range of 1444.32–1870.45 MPa, elongation at break in the range of 23.7%–30.8%, and tensile strength in the range of 52.21–59.38 MPa.

Highly efficient synthesis of sustainable bisphenols from hydroxycinnamic acids

A series of bisphenols were efficiently prepared from bio-based hydroxycinnamic acids via thermal decarboxylation followed by [Ru]-catalyzed olefin metathesis.

Effect of Processing Parameters on the Synthesis of Bisphenols, Monomers for Producing Polyester Polymers and Fibres

The effect of processing parameters on the synthesis of a series of bisphenols in the presence of an HCl:H2S catalyst was studied. It was shown that the reaction was highly selective at a 1:10 ketone:phenol mole ratio. The reaction rate was strongly affected by the amount of catalyst up to a 1:0.25 ketone:HCl mole ratio whereas the required amount of promoter (H2S) was <0.15 mol/mol of ketone. The optimum synthesis temperature fell in the range 30-50°C and depended on the structure of the synthesized bisphenol. A series of bisphenols based on various phenols and ketones were synthesized under the selected optimum conditions.

Preparation and properties of bisphenol A‐based bis‐phthalonitrile composite laminates

AbstractA series of bisphenol A (BPA)‐based 2,2‐bis‐[4‐(3,4‐dicyanophenoxy)phenyl]propane (BAPh) prepolymers and polymers were prepared using BPA as a novel curing agent. Ultraviolet–visible and Fourier transform infrared spectroscopy spectrum were used to study the polymerization reaction mechanism of the BAPh/BPA polymers. The curing behaviors were studied by differential scanning calorimetry and dynamic rheological analysis, the results indicated that the BAPh/BPA prepolymers exhibit large processing windows (109.5–148.5°C) and low complex viscosity (0.1–1 Pa·s) at moderate temperature, respectively. Additionally, the BAPh/BPA/glass fiber (GF) composite laminates were manufactured and investigated. The flexural strength and modulus of the composite laminates are 548.7–632.8 MPa and 25.7–33.2 GPa, respectively. The thermal stabilities of BAPh/BPA/GF composite laminates were studied by thermogravimetry analysis. The temperatures at 5% weight loss (T5%) of the composite laminates are 508.5–528.7°C in nitrogen and 508.1–543.2°C in air. In conclusion, the BAPh/BPA systems can be used as superior matrix materials for numerous advanced composite applications. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013

Synthesis and carbonic anhydrase inhibitory properties of novel bromophenols and their derivatives including natural products: Vidalol B

A series of bisphenol, bromophenol, and methoxyphenol derivatives (2–24) including the natural bromophenols vidalol B, 3,4,6-tribromo-5-(2,5-dibromo-3,4-dihydroxybenzyl)benzene-1,2-diol (2) and 5,5′-methylenebis(3,4,6-tribromo-benzene-1,2-diol) (3) were prepared. In the current study, inhibition of four human carbonic anhydrase (hCA, EC 4.2.1.1) isozymes, I, II, IV, and VI, with these compounds 2–24 was investigated. The compounds 2–24 were found to be promising carbonic anhydrase inhibitors, some of which showed interesting inhibitory activities. Some of the compounds investigated here showed effective hCA inhibitory activity, and might be used as leads for generating novel carbonic anhydrase inhibitors which are valuable drug candidates for the treatment of glaucoma, epilepsy, gastric and duodenal ulcers, neurological disorders, and osteoporosis.

Synthesis and fungicidal properties of new bisphenol-containing oligoorganosiloxanes

New fungicidal and antimicrobial siloxane oligomers were prepared on the basis of γ-aminopropyltriethoxysilane and a series of bisphenols. Chemical immobilization of these oligomers on the surface of various fabrics was studied with the aim to develop textile materials resistant to microbiological degradation.

Inhibition of human carbonic anhydrase isozymes I, II and VI with a series of bisphenol, methoxy and bromophenol compounds

Carbonic anhydrase inhibitors (CAI) are valuable molecules as they have several therapeutic applications, including anti-glaucoma activity. In this study, inhibition of three human carbonic anhydrase (hCA, EC 4.2.1.1) isozymes I, II and VI with a series of bisphenol and bromophenol derivatives was investigated. Molecular docking studies of a set of such inhibitors within CA I and II were also performed. KI values of the molecules 2–9 were in the range of 10.025–892.109 μM for hCA I, 1.437–59.107 μM for hCA II and 11.143–919.182 μM for hCA VI, respectively. Reported inhibitory activities of molecules 2–9 will assist in better understanding of structure-activity relationship studies of CAI.

Synthesis and characterization of poly(arylene ether) containing cyanate ester networks

A series of bisphenols containing ether linkage were prepared from halo phenol/dihalo compound and dihydroxy compounds in the presence of K2CO3. The bisphenols were transformed to cyanate esters by treatment with cyanogen bromide using triethyl amine catalyst. The structure of all the five bisphenols and the cyanate esters were structurally confirmed by FT-IR, 1H-NMR and 13C-NMR spectral methods and elemental analysis. The cyanate esters were cured at 100 °C (30 min) → 150 °C (30 min) → 200 °C (60 min) → 250 °C (3 hr). The thermal properties of the cured resins were studied by DSC and TGA. DSC analysis shows that these cyanate esters exhibit Tg in the range of 203–234 °C. The CE(c) has the highest glass transition temperature. The cyanate ester CE(e) shows the lowest Tg which is due to its asymmetric structure. The initial degradation temperature of the cured resins was found to be in the range of 324–336 °C. The Limiting Oxygen Index (LOI) value, determined by Van Krevelen’s equation, is in the range of 35.5–38.7.

Bisphenol A directly targets tubulin to disrupt spindle organization in embryonic and somatic cells.

There is increasing concern that animal and human reproduction may be adversely affected by exposure to xenoestrogens that activate estrogen receptors. There is evidence that one such compound, Bisphenol A (BPA), also induces meiotic and mitotic aneuploidy, suggesting that these kinds of molecules may also have effects on cell division. In an effort to understand how Bisphenol A might disrupt cell division, a phenotypic analysis was carried out using sea urchin eggs, whose early embryonic divisions are independent of zygotic transcription. Fertilized Lytechinus pictus eggs exposed to BPA formed multipolar spindles resulting in failed cytokinesis in a dose-dependent, transcriptionally independent manner. By use of novel biotinylated BPA affinity probes to fractionate cell-free extracts, tubulin was identified as a candidate binding protein by mass spectrometry, and BPA promoted microtubule polymerization and centrosome-based microtubule nucleation in vitro but did not appear to display microtubule-stabilizing activity. Treatment of mammalian cells demonstrated that BPA as well as a series of Bisphenol A derivatives induced ectopic spindle pole formation in the absence of centrosome overduplication. Together, these results suggest a novel mechanism by which Bisphenol A affects the nucleation of microtubules, disrupting the tight spatial control associated with normal chromosome segregation, resulting in aneuploidy.

Laser pyrolysis of characterized cyanurate network polymers

AbstractA series of bisphenol A dicyanate network polymers with degree of crosslinking varied by addition of 4‐cumylphenylcyanate were prepared and characterized by model compound study, infrared spectroscopy, DSC, TGA, and statistical analysis. Laser ablation energy measurements varied from 14 to 18 kJ/g and were found to linearly increase with degree of crosslinking. Comparative ablation energy analysis was made with other aromatic, nonaromatic, linear, and crosslinked polymers.