Synthesis and characterization of copolycarbonates from melt transesterification

Liaw, Der‐Jang; Chang, Ping

doi:10.1016/0032-3861(96)87651-8

Cited by 17 publications

(29 citation statements)

References 21 publications

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“…To our knowledge, a viable industrial method for the preparation of alkylene diphenyl dicarbonates from alkane diols and a carbonate‐providing compound has not been previously developed. Therefore, the alkylene diphenyl dicarbonates were synthesized (step 1 in Scheme ) in a solution of alkane diols and PCF in the presence of excess pyridine, according to previously published procedure 27. Pyridine acted as an acid acceptor and reacted with PCF to form an ionic adduct that was more reactive than PCF 21.…”

Section: Resultsmentioning

confidence: 99%

“…The various alkylene diphenyl dicarbonate monomers were synthesized by the reaction of the corresponding alkane diol with PCF (step 1 in Scheme ), according to a previously published procedure 27. The preparation of the various alkylene diphenyl dicarbonates were conducted with either dichloromethane or tetrahydrofuran as the solvent.…”

Section: Methodsmentioning

confidence: 99%

“…according to a previously published procedure. 27 The preparation of the various alkylene diphenyl dicarbonates were conducted with either dichloromethane or tetrahydrofuran as the solvent. A typical procedure is described here for the synthesis of Bu-1,4-D DPDC.…”

Section: Monomer Synthesismentioning

confidence: 99%

“…Therefore, the alkylene diphenyl dicarbonates were synthesized (step 1 in Scheme 1) in a solution of alkane diols and PCF in the presence of excess pyridine, according to previously published procedure. 27 Pyridine acted as an acid acceptor and reacted with PCF to form an ionic adduct that was more reactive than PCF. 21 The reaction proceeded via pyridine-catalyzed nucleophilic displacement of the chloride of PCF with the alcohol group of the alkane diol.…”

Section: Monomer Synthesis and Characterizationmentioning

confidence: 99%

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A new, nonphosgene route to poly(bisphenol a carbonate) by melt‐phase interchange reactions of alkylene diphenyl dicarbonates with bisphenol A

Sweileh

A-Hiari

Aiedeh

2008

J of Applied Polymer Sci

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This article describes a new, nonphosgene method for the synthesis of poly(bisphenol A carbonate) (PC). The method involves three steps: the reaction of an aliphatic diol with phenyl chloroformate to form an alkylene diphenyl dicarbonate, the reaction of the alkylene diphenyl dicarbonate with bisphenol A to produce an aromatic–aliphatic polycarbonate, and the thermal treatment of the polycarbonate at 180–210°C under a stream of nitrogen with Ti(OBu)4 to give PC and a cyclic alkylene carbonate. The method furnished low to moderate molecular masses of PC upon the complete elimination of the aliphatic moieties. The approach may be considered a new method, based on polycarbonate thermochemical degradation, for the synthesis of cyclic aliphatic carbonates. The obtained polymers were characterized by intrinsic viscosity and IR, 1H‐NMR, and 13C‐NMR spectroscopy. The thermal treatment step was conducted in a glass reaction tube at 180–210°C under a stream of nitrogen, and the reaction was completed by heating to 250°C. In the thermal treatment step, semisolid effluents composed of cyclic alkylene carbonates were formed and subsequently eliminated from the reaction mixture. Heating to 250°C under nitrogen or under a dynamic vacuum furnished the pure aromatic PC residue. This intrachange reaction provides a flexible method for the synthesis of polycarbonates with alkylene diols containing two or three methylene groups, from which the pure PC homopolymer can be prepared. The potential of this approach was demonstrated by the successful synthesis of PC homopolymer from five different polycarbonates with a bisphenol A unit linked to 1,2‐propylene, 1,3‐propylene, 2‐methyl‐1,3‐propylene, 2,2‐dimethyl‐1,3‐propylene, and 1,3‐butylene as the alkane chains. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2008

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Monomer Synthesismentioning

confidence: 99%

Section: Monomer Synthesis and Characterizationmentioning

confidence: 99%

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A new, nonphosgene route to poly(bisphenol a carbonate) by melt‐phase interchange reactions of alkylene diphenyl dicarbonates with bisphenol A

Sweileh

A-Hiari

Aiedeh

2008

J of Applied Polymer Sci

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“…The semicrystalline behavior of PA6 should be associated with the fact that the polar sulfone group has a larger intermolecular force between the polymer chains which led to a higher crystallinity. [14,15] The other polymers exhibited amorphous diffraction patterns. Table 3 summarizes the thermal behavior of these polyamides which was evaluated by means of thermogravimetry (TG) and DSC.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and properties of new polyamides derived from 2,2-bis[4-[2-(4-aminophenoxy)ethoxy]phenyl]sulfone by direct polycondensation

Liaw

1999

Polym. Adv. Technol.

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A series of new polyamides containing both sulfone and oxyethylene moieties in the polymer chain was prepared by the direct polycondensation of the diamine monomer 2,2‐bis[4‐[2‐(4‐aminophenoxy)ethoxy]phenyl]sulfone (BAEPS) and various aromatic dicarboxylic acids in N‐methyl‐2‐pyrrolidinone (NMP) using triphenyl phosphite and pyridine as condensing agents. Polymers were produced with inherent viscosities of 0.30–0.60 dl/g and identified by elemental analysis, and infrared and nuclear magnetic resonance spectra. Most of the polymers were readily dissolved in polar solvents such as NMP, dimethylsulfoxide, N,N‐dimethylacetamide, N,N‐dimethylformamide and m‐cresol at room temperature. Polymers containing rigid and symmetric p‐phenylene, naphthalene and p‐biphenylene moieties revealed a crystalline nature and showed no solubility in organic solvents. These polyamides had 10% weight loss temperatures ranging between 423 and 465 °C in nitrogen atmosphere and glass transition temperatures between 170 and 305 °C. The polymers with crystallinity nature exhibited melting endotherms (Tm) below 386 °C in differential scanning calorimetry trace. Copyright © 1999 John Wiley & Sons, Ltd.

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Preparation and properties of flame-retardant polyphosphate esters: Low-temperature solution polycondensation of 3,3,?5,5?-tetrabromobisphenol AF and aryl phosphorodichloridates

Liaw¹

1997

J. Appl. Polym. Sci.

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This article describes the syntheses of aromatic polyphosphates from the reaction of various aryl phosphorodichloridates with 3,3 ,5,5-tetrabromobisphenol AF (TBPAF) in a chlorinated hydrocarbon solvent under low-temperature conditions. The new polyphosphates obtained were characterized by infrared, 13C and 31 P nuclear magnetic resonance spectra, elemental analysis, inherent viscosity, thermogravimetric analysis, differential scanning calorimetry, X-ray diffraction, limiting oxygen index, contact angle, and molar mass measurement. All of the polyphosphates obtained had high yields, and the inherent viscosities were in the range 0.12-0.15 dL g 01 . All of the polymers start degrading between 210 and 267ЊC and had 14-26% residual mass at 700ЊC in nitrogen. Polymer E, having a methoxy group in the side chain phenyl ring, showed better thermal stability than the other polymers. The X-ray diffraction patterns revealed that all of the polyphosphates were amorphous. These polyphosphates had glass transition temperatures between 140 and 154ЊC. Polymers obtained from TBPAF had excellent flame retardency, as indicated by high limiting oxygen index values in the range of 63-68. The water contact angles ( u w ) of all of the polyphosphates were in the range of 74-87Њ. The contact angles of polymers A and B were larger than those of other polyphosphates that contain more oxygen (polymers C and E) or bromine atoms (polymer D).

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Synthesis and characterization of copolycarbonates from melt transesterification

Cited by 17 publications

References 21 publications

A new, nonphosgene route to poly(bisphenol a carbonate) by melt‐phase interchange reactions of alkylene diphenyl dicarbonates with bisphenol A

A new, nonphosgene route to poly(bisphenol a carbonate) by melt‐phase interchange reactions of alkylene diphenyl dicarbonates with bisphenol A

Synthesis and properties of new polyamides derived from 2,2-bis[4-[2-(4-aminophenoxy)ethoxy]phenyl]sulfone by direct polycondensation

Preparation and properties of flame-retardant polyphosphate esters: Low-temperature solution polycondensation of 3,3,?5,5?-tetrabromobisphenol AF and aryl phosphorodichloridates

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