CHEMICALS
New Oxide Polymers Developed by GE General Electric plans commercial production of first in a family of polyphenylene oxide products General Electric is planning commercial production of the first of a family of polyphenylene oxide (PPO) products. PPO grade C-1001 is a polyether of 2,6-dimethylphenol and is based on an oxidative coupling process. The process, discovered by Dr. Allan S. Hay, organic chemist at GE's research laboratory, Schenectady, N.Y., involves the oxidation of 2,6-dimethylphenol with either air or pure oxygen in the presence of a copper-amine complex catalyst. The company now makes small amounts in a 500,000 lb.-per-year pilot plant at Pittsfield, Mass. However, GE plans a larger plant, likely at Mount Vernon, Ind., the site of its PPO monomer plant. The new plant's rated capacity will be 10 million lb. per year, and future expansion increments will be 10 million lb. Although future plans are flexible, GE will not place more than 80 million lb. capacity at any one plant location. Such size is remote at the present price, $1.50 a pound. When the new plant is on stream in 1966, the oxide polymer will be 81.00 a pound; a later drop to 50 cents a pound is expected by the company. GE has entered a joint venture with Algemene Kunstzijde Unie, N.V., to make and sell C-1001 in Europe. The company is N.V. Polychemie AKUGE and is headquartered in Arnheim, the Netherlands. GE says that its grade C-1001 offers a combination of properties not previously available in an engineering thermoplastic. These properties include a useful temperature range of from less than - 2 7 5 ° F. to 375° F., resistance to aqueous chemicals and to steam, excellent mechanical properties, and excellent dielectric characteristics. Other assets of C-1001 are low specific gravity, self-extinguishing character, and low mold shrinkage. Physical Properties. PPO grade C-1001 has a brittle point of less than —275° F., and a heat deflection point of about 375° F., at a 264 p.s.i. load.
It can withstand intermittent exposure to temperatures as high as 400° F. under no load or light load conditions. The new polymer is inert to aqueous chemicals and steam. Enhancing its chemical resistance are resistance to staining, low moisture absorption, and nontoxicity. Company tests show the new polymer to have excellent mechanical properties. Tests show that PPO grade C-1001 is a tough, rigid, and dimensionally stable product. At 257° F., the polymer has an average tensile modulus between 330,000 and 340,000 p.s.i. Flexural
modulus, at 73° F., is between 350,000 and 380,000 p.s.i.; water absorption at 73° F. (seven days) is 10%. PPO withstands loads well, having only 0.75% creep after 300 hr. at room temperature under a 3000 p.s.i. load. And since water absorption is low, the polymer retains dimensional stability in a variety of environments. Dielectric strength of the new polymer is 400 to 500 volts per mil, in the range of common thermoplastics. It maintains its performance with little or no change over a broad range of cycles and temperatures. The company feels that the poly-
FORMS. General Electric's Dr. Allan S. Hay watches polyphenylene oxide polymer form during oxidative coupling reaction, GE plans commercial production of first new polymers DEC.
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mer's resistance to steam, detergents, fungus, and aqueous chemicals qualifies it for a variety of hospital and laboratory equipment and apparatus, including many items that are currently made of stainless steel and glass. Its chemical resistance and high-temperature perfomiance also indicate some uses in the chemical and food industries, among which are pump housings, impellers, pipe, and valves. Production. Facilities for producing PPO grade C-1001 will be built and should be on stream in 12 to 18 months. By the oxidative coupling process, 2,6-dimethylphenol can be pohmerized homogeneously or heterogeneously. In the homogeneous reaction, the molecular weight is determined by the viscosity of the product and the reaction is stopped when the desired molecular weight is attained. The homogeneous product is placed in either methanol or isopropyl alcohol to precipitate the polymer. A difficulty involved in this process is that the water, which is a by-product of the polymerization, is immiscible in the solvent (either benzene or toluene) and must be removed throughout the reaction, since water makes the copper-amine complex ineffective as an oxidation catalyst. This is done either by evaporation with a stream of air or oxygen or addition of a drying agent to the reaction. The heterogeneous reaction uses a mixture solvent—benzene, toluene, or dichlorobenzene along with isopropyl alcohol. The molecular weight is determined by the concentration of the components of the mixture. The reaction is heterogeneous because there is both a solvent and a nonsolvent in the solvent mixture. The polymer is insoluble in isopropyl alcohol and, therefore, precipitates out of solution. The water problem does not exist in this reaction because water is miscible in the mixture solvent and does not affect the catalyst. Both reactions are high in y i e l d more than 90%, according to Dr. John R. Elliot, manager of organic chemistry studies at GE's Schenectady lab. However, he says the company hasn't decided which route to take. The GE process isn't the only route to PPO. Dr. Charles C. Price, chairman ,of the chemistry department at the University of Pennsylvania, has also made the polymer. Dr. Price treated 2,6-dimethyl-4-biOniophenol with potassium ferricyanide.
Test Shows Alcohol Ethoxylates Biodegradable A field test demonstrating the biodegradability of Union Carbide's linear secondary alcohol ethoxylate surfactants has been completed. Test results showed that biodégradation of the test surfactants averaged 90 to 93%. Furthermore, foaming was no problem. In comparison, hard surfactants (alkylbenzene sulfonates and nonylphenol ethoxylates) in the detergents normally used averaged 56 to 60% degradation, and foaming was severe. Conclusion drawn by participants in the test is that with efficient aerobic waste treatment, the linear secondary alcohol ethoxylate surfactants are biologically degradable to about the same extent as the over-all organic matter entering the treatment plant. Similar results were obtained with linear alkylate sulfonate (LAS) in a previous test at the same location. By the middle of next year, Union Carbide will produce linear secondary alcohol ethoxylate surfactants commercially at Texas City, Tex. The products are for use in detergents, with or without LAS. A question yet to be answered is how well the variety of soft surfactants coming to market will decompose under relatively anaerobic conditions existing in some septic tanks, cesspools, and sewage disposal facilities. Union Carbide and others are investigating this question. Test site was the Elm Farm Mobile Home Park at Woodbridge, Va., a community of 111 trailer homes whose wastewater is processed in an extended-aeration activated-sludge plant. The Elm Farm location was chosen because biodegradability comparisons of linear alkylate sulfonate and alkylbenzene sulfonate (ABS) surfactants were successfully concluded there last January by Colgate-Palmolive and Johns Hopkins. Colgate-Palmolive formulated the household detergents for the sevenweek test, which was directed by Dr. Charles E. Renn, professor of sanitary engineering at Johns Hopkins. Linear secondary alcohol ethoxylate surfactants produced at Carbide's Institute, W.Va., interim production facility were used. Neither ABS nor LAS were included in these formulations. The detergents included low-suds laundry powder, light-duty liquid detergent, scouring powder, and chil-
CH 3
useful in preparing polyester resins of exceptional utility
HO-CHa-C-CHaOH CH 3 Neopentyl Glycol— gem-2t2-Dimethyl-1,3-propanediol
OH CH3
CH3
