Brominated Poly(Phenylene Oxide)s. I. Polymerization of Mono-, Di- and Tribromo-2,6-Dimethylphenol

White, Donald R.; Klopfer, H. J.

doi:10.1021/bk-1975-0006.ch011

Cited by 9 publications

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“…Although not as commercially attractive as the oxidative coupling route because of the presence of halogen, this procedure has been useful for the preparation of brominated PPO resins. 6 Hay found that a large number of phenols could be oxidatively polymerized analogously to 2,6-dimethylphenol. 2,6-Diphenylphenol was converted to the totally aromatic polyether and was found to have utility in applications such as an organic phase for gas chromatography and in gas absorption equipment.…”

mentioning

confidence: 99%

Perspective: Comments on “Polymerization by oxidative coupling. II. Oxidation of 2,6-disubstituted phenols,” by Allan S. Hay,J. Polym. Sci., 58, 581 (1962)

Takekoshi¹,

White²

1996

J. Polym. Sci. A Polym. Chem.

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The discovery that high molecular weight polymers could be prepared by oxidative coupling reactions has opened up many routes to new classes of polymers and led to new major industrial processes. The initial work by Allan S. Hay grew from work at the General Electric Research Laboratory on metal catalyzed oxidation of simple organic materials, such as xylenes, to produce phthalic acids for alkyd resins. Among other substrates examined were phenols, thiophenols, and amines. The observation that a highly selective polymerization reaction could be achieved by blocking reactive sites in the ortho positions of phenol with methyl groups spurred an extensive research program on oxidative coupling.' From this work came knowledge of the poly-1,4-phenylene ether structure of the polymers from 2,6-disubstituted phenols, the scope of the reaction, the mechanism of the polymerization, and the determination of the physical properties of the polymeric products.2The polymerization process for the conversion of 2.6-dimethylphenol to poly(2,6-dimethyl-l,4-phenylene oxide) (PPO" resin) was sufficiently straightforward to be commercially attractive, and efforts were made to scale up and optimize the process. However, an unusual characteristic of the polymer was its high glass transition temperature of -208OC, which meant high processing temperatures would be required for commercial utilization. Under these conditions, polymer degradation via oxidation and thermal side reactions became an issue. The problem was overcome by the discovery that PPO resin formed homogeneous blends with polystyrene3 and

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mentioning

confidence: 99%

Perspective: Comments on “Polymerization by oxidative coupling. II. Oxidation of 2,6-disubstituted phenols,” by Allan S. Hay,J. Polym. Sci., 58, 581 (1962)

Takekoshi¹,

White²

1996

J. Polym. Sci. A Polym. Chem.

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Polyethers, Aromatic

White

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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The aromatic polyethers described in this article are engineering thermoplastics which have excellent physical properties and desirable high temperature properties. Two general classes of materials are described. One class of polyethers comprises polymers with only arylene ether linkages in the backbone, ie, the 1,4‐polyphenylene oxides. The principal commercial material, poly(2,6‐dimethyl‐1,4‐phenylene oxide) is prepared by oxidative coupling polymerization of 2,6‐dimethylphenol. Its synthesis, reaction mechanism, and properties are described. In addition, compatible blends of poly(phenylene oxides) with polymers such as polystyrene, as well as other types of blends, are mentioned. A second general class of aromatic polyethers that is covered consists of materials containing alternating sequences of polyarylene ethers and other arylene units which are linked by functional groups other than ethers. The latter group includes the commercial materials: polyethersulfones, polyetherketones, and polyetherimides. Syntheses and properties of these are presented.

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Polyethers, Aromatic

Yeager¹

2004

Encyclopedia of Polymer Science and Technology

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The aromatic polyethers described in this article are engineering thermoplastics which have excellent physical properties and desirable high temperature properties. Two general classes of materials are described. One class of polyethers comprises polymers with only arylene ether linkages in the backbone, ie, the 1,4‐polyphenylene oxides. The principal commercial material, poly(2,6-dimethyl-1,4-phenylene oxide) is prepared by oxidative coupling polymerization of 2,6-dimethylphenol. Its synthesis, reaction mechanism, and properties are described. In addition, compatible blends of poly(phenylene oxides) with polymers such as polystyrene, as well as other types of blends, are mentioned. A second general class of aromatic polyethers that is covered consists of materials containing alternating sequences of polyarylene ethers and other arylene units which are linked by functional groups other than ethers. The latter group includes the commercial materials: polyethersulfones, polyetherketones, and polyetherimides. Syntheses and properties of these are presented.

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Brominated Poly(Phenylene Oxide)s. I. Polymerization of Mono-, Di- and Tribromo-2,6-Dimethylphenol

Cited by 9 publications

References 0 publications

Perspective: Comments on “Polymerization by oxidative coupling. II. Oxidation of 2,6-disubstituted phenols,” by Allan S. Hay,J. Polym. Sci., 58, 581 (1962)

Perspective: Comments on “Polymerization by oxidative coupling. II. Oxidation of 2,6-disubstituted phenols,” by Allan S. Hay,J. Polym. Sci., 58, 581 (1962)

Polyethers, Aromatic

Polyethers, Aromatic

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