Phenol polyphenylene oxides

Trilialophenols can be converted to poly(dihaloph.enylene oxide)s by a reaction that resembles radical-initiated displacement polymerization. In one procedure, either a copper or silver complex of the phenol is heated to produce a branched product (50). In another procedure, a catalytic quantity of an oxidizing agent and the dry sodium salt in dimethyl sulfoxide produces linear poly(2,6-dichloro-l,4-polyphenylene oxide) (51). The polymer can also be prepared by direct oxidation with a copper—amine catalyst, although branching in the ortho positions is indicated by chlorine analyses (52). 

These results demonstrate some interesting chemical principles of the use of acrylic adhesives. They stick to a broad range of substrates, with some notable exceptions. One of these is galvanized steel, a chemically active substrate which can interact with the adhesive and inhibit cure. Another is Noryl , a blend of polystyrene and polyphenylene oxide. It contains phenol groups that are known polymerization inhibitors. Highly non-polar substrates such as polyolefins and silicones are difficult to bond with any technology, but as we shall see, the initiator can play a big role in acrylic adhesion to polyolefins. 

Poly(ethylene terephtlhalate) Phenol-formaldehyde Polyimide Polyisobutylene Poly(methyl methacrylate), acrylic Poly-4-methylpentene-1 Polyoxymethylene polyformaldehyde, acetal Polypropylene Polyphenylene ether Polyphenylene oxide Poly(phenylene sulphide) Poly(phenylene sulphone) Polystyrene Polysulfone Polytetrafluoroethylene Polyurethane Poly(vinyl acetate) Poly(vinyl alcohol) Poly(vinyl butyral) Poly(vinyl chloride) Poly(vinylidene chloride) Poly(vinylidene fluoride) Poly(vinyl formal) Polyvinylcarbazole Styrene Acrylonitrile Styrene butadiene rubber Styrene-butadiene-styrene Urea-formaldehyde Unsaturated polyester... 

Cellulose Esters Epoxy Resins Lignins Polystyrene Poly (2-vinyl pyridine) Polyvinyl Chloride Polymethyl methacrylate Polyphenylene Oxide Phenolics Polycarbonate Polyvinyl Acetate, etc. Polyvinyl butyral SBR rubber, etc., etc. 

Polyphenylene oxide (PPO) is produced by the condensation of 2,6-dimethylphenol. The reaction occurs by passing oxygen in the phenol solution in presence of CU2CI2 and pyridine ... 

Polyacetal Homopolymer Polyelherimide Phenolic Resin Polypropylene Polyvmylidene Difluonde Polyphenylene Oxide Polyphenylene Oxide (Glass Filled) Polyethersulphone I ill ll I i jH... 

Between 250 and 450°F (121 and 232°C), plastics used include glass or mineral-filled phenolics, melamines, alkyds, silicones, nylons, polyphenylene oxides, polysulfones, polycarbonates, methylpentenes, fluorocarbons, polypropylenes, and diallyl phthalates. The addition of glass fillers to the thermoplastics can raise the useful temperature range as much as 100°F and at the same time shortens the molding cycle. 

Color Urea, melamine, polycarbonate, polyphenylene oxide, polysulfone, polypropylene, diallyl phthalate, and phenolic are examples of what is needed in the temperature range above 200°F (94°C) for good color stability. Most TPs will be suitable below this range. 

Moisture Deteriorating effects of moisture are well known as reviewed early in this chapter (OTHER BEHAVIOR, Drying Plastic). Examples for high moisture applications include polyphenylene oxide, polysulfone, acrylic, butyrate, diallyl phthalate, glass-bonded mica, mineral-filled phenolic, chlorotrifluoroethylene, vinylidene, chlorinated polyether chloride, vinylidene fluoride, and fluorocarbon. Diallyl phthalate, polysulfone, and polyphenylene oxide have performed well with moisture/steam on one side and air on the other (a troublesome... 

Dimensional stability There is plastics with very good dimensional stability, and they are suitable where some age and environmental dimensional changes are permissible. These materials include polyphenylene oxide, polysulfone, phenoxy, mineral-filled phenolic, diallyl phthalate, epoxy, rigid vinyl, styrene, and various RPs. Such products will gain from an after-bake for dimensional stabilization. Glass fillers will improve the dimensional stability of all plastics. 

Phenolic glass and a diallyl phthalate glass material are available with very low shrinkage. Glass and other mineral fillers minimize the thermal expansion differential problem. Phenoxy and polyphenylene oxides are examples of being low in shrinkage and thermal expansion. 

Many of the commercially important plastics such as polystyrene, polyamide, polyester, polycarbonate, polysulfone, polyphenylene oxide alloys, epoxy, and phenolics lack good impact... 

Aromatic cyclic chains are more stable than aliphatic catenated carbon chains at elevated temperatures. Thus linear phenolic and melamine polymers are more stable at elevated temperatures than polyethylene, and the corresponding cross-linked polymers are even more stable. In spite of the presence of an oxygen or a sulfur atom in the backbones of polyphenylene oxide (PPO), polyphenylene sulfide (PPS), and polyphenylene sulfone, these polymers are... 

Highlighting some of these post-phenolic developments, we saw polyvinyl chloride introduced in 1927, acrylics in 1936, nylon in 1938, and fluorocarbon in 1943. ABS (acrylonitrile-butadiene-styrene) was introduced in 1948, acetal in 1956, polycarbonate in 1957, polyphenylene oxide in 1964, and polysulfone in 1965. 

Engineering plastics are most frequently thought of as the acetals, nylons, fluorocarbons, phenolics, polycarbonate, and polyphenylene oxide, to name just a few. These are indeed engineering materials and for such applications are usually used in relatively small... 

COUPLING (Chemical). Reactions for the formation of chemical compounds usually by establishing a valence bond between a carbon atom and a nitrogen atom. Phenols and several other organic substances are also said "to couple. Polyphenylene oxides, thermoplastic materials, are produced by means of oxidative-coupling technology. 

PC PE PES PET PF PFA PI PMMA PP PPO PS PSO PTFE PTMT PU PVA PVAC PVC PVDC PVDF PVF TFE SAN SI TP TPX UF UHMWPE UPVC Polycarbonate Polyethylene Polyether sulfone Polyethylene terephthalate Phenol-formaldehyde Polyfluoro alkoxy Polyimide Polymethyl methacrylate Polypropylene Polyphenylene oxide Polystyrene Polysulfone Polytetrafluoroethylene Polytetramethylene terephthalate (thermoplastic polyester) Polyurethane Polyvinyl alcohol Polyvinyl acetate Polyvinyl chloride Polyvinyl idene chloride Polyvinylidene fluoride Polyvinyl fluoride Polytelrafluoroethylene Styrene-acrylonitrile Silicone Thermoplastic Elastomers Polymethylpentene Urea formaldehyde Ultrahigh-molecular-weight polyethylene Unplasticized polyvinyl chloride... 

When phenols are oxidized by molecular oxygen in the presence of copper-amine complexes as catalysts, oxidative polymerization to polyphenylene ethers results,344-349 e.g.,... 

Various adhesives can be used to bond polyphenylene oxide to itself or to other substrates. Parts must be prepared by sanding or by chromic acid etching at elevated temperature. Methyl alcohol is a suitable solvent for surface cleaning. The prime adhesive candidates are epoxies, modified epoxies, nitrile phenolics, and polyurethanes. Epoxy adhesive will provide tensile shear strength on abraded polyphenylene oxide substrates of 600 to 1300 psi and 1300 to 2200 psi on etched (chromic acid) substrates.71... 

Dimethylphenol (206) was treated with NaBiOs in benzene to afford polyphenylene oxide (659) and 3,3, 5,5 -tetramethyldiphenoquinone (207) in 74 and 12% yields, respectively . This result is similar to that of Mn02 oxidation (see Scheme 126). In contrast, the use of AcOH instead of benzene as a solvent provided the corresponding quinol acetate 864 and 207 in 38 and 15% yields, respectively (Scheme 174) °. Oxidation of 2,4,6-tri(tert-butyl)phenol (73) with NaBiOs in AcOH afforded the p-quinol acetate (865) as a major product (62%) and the o-quinol acetate (866) as a minor product (22%). In contrast, Pb(OAc)4 oxidation of 73 in AcOH provided 866 as a main product (60%) (see Scheme 170). Oxidation of alkoxyphenols and other phenols has also been studied . ... 

Phenols are oxidized by NaBiO3 to polyphenylene oxides, quinones, or cyclohexa-2,4-dienone derivatives, depending on the substituents and the reaction conditions [263]. For example, 2,6-xylenol is oxidized in AcOH to afford a mixture of cyclohexa-dienone and diphenoquinone derivatives (Scheme 14.123) [264] and is oxidatively polymerized in benzene under reflux to give poly(2,6-dimethyl-l,4-phenylene) ether (Scheme 14.124) [265]. Substituted anilines and a poly(phenylene oxide) are oxidatively depolymerized by NaBiO, to afford the corresponding anils [266]. Nal iO, oxidizes olefins to vicinal hydroxy acetates or diacetates in low to moderate yield [267]. Polycyclic aromatic hydrocarbons bearing a benzylic methylene group are converted to aromatic ketones in AcOH under reflux (Scheme 14.125) [268]. 

Phenols and olefins are oxidized to polyphenylene oxides and v/c-diol derivatives, respectively. 

ORIGIN/INDUSTRY SOURCES/USES from coal tar fractionation and coal processing intermediate in manufacturing of phenolic antioxidants pharmaceuticals plastics resins disinfectants solvents insecticides fungicides rubber chemicals polyphenylene oxide dyestuffs cresylic acid constituent wetting agent additive of lubricants and gasoline... 

Fluorinated ethylene propylene copolymer Melamine formaldehyde Phenol-furfural Polyphenylene oxide Polysulfone Zone 5... 

A rigid foam is defined as one in which the polymer matrix exists in the crystalline state or, if amorphous, is below its Tg. Following from this, a flexible cellular polymer is a system in which the matrix polymer is above its Tg. According to this classification, most polyolefins, polystyrene, phenolic, polyycarbonate, polyphenylene oxide, and some polyurethane foams are rigid, whereas rubber foams, elastomeric polyurethanes, certain polyolefins, and plasticized PVC are flexible. Intermediate between these two extremes is a class of polymer foams known as semirigid. Their stress-strain behavior is, however, closer to that of flexible systems than to that exhibited by rigid cellular polymers. 

Polyethers are obtained from three different classes of monomers, namely, carbonyl compounds, cyclic ethers, and phenols. They are manufactured by a variety of polymerization processes, such as polymerization (polyacetal), ring-opening polymerization (polyethylene oxide, polyprophylene oxide, and epoxy resins), oxidative coupling (Polyphenylene oxide), and polycondensation (polysulfone). 

Between 250 and 450F (121 and 232C), glass or mineral-filled phenolics, melamine, alkyd, silicone, nylon, polyphenylene oxide. 

Uses Disinfectant solvent for wire enamels pharmaceuticals insecticides fungicides herbicides plasticizers mbber chemicals paints additives to lubricants and gasoline mfg. of polyphenylene oxide wetting agents dyestuff synthetic resin comonomer for alkali-resist, phenolic resins froth flotation agent engine cleaner ingred. 

Techniques for chloromethylating polyaiylether sulfones, polyphenylene oxide, phenolic resins, and model compounds were described recently. When the subsequent products are converted... 

Polyphenylene-Oxide (PPO, Noryl) PPO appeared in 1964 as a conjugated oxidation product of phenolic monomers. 

Techniques for chloromethylating polyarylether sulfones, polyphenylene oxide, phenolic resins, and model compounds were described recently [191]. When the subsequent products are cmiverted to quaternary amines, there is a decrease in the quatemization rate with increase in degree of substitutimi. This may be due to steric effects imposed by restricted rotation of the polymeric chains [191]. This phenomenon was not observed in quatemization of poly(chloromethyl styrene). The chloromethylation reaction of a polysulfone with chloromethyl ether, catalyzed by stannic chloride, can be illustrated as follows ... 

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