Plastics

pared to the three major general purpose polymers, the engineering plastics are of prime importance. An unprecedented number of new polymers with unus...
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annual review

R. B. SEYMOUR

Plastics Continued research and deuelopment extend auailabilip of engineering plastics, and introduction

of new functional materials to promote growth of this large industv

s noted in previous reviews, the American polymer

A industry is technically

mature and is benefiting from previous investments in research, development, and standardization. The worldwide growth rate of plastics production now exceeds that of the United States. However, the production last year (in excess of 10 billion pounds) exceeded the optimistic predictions presented in the report of the Paley Commission in 1952. The engineering (6A) and technical (3A) highlights of recent plastics progress have been cited. I n spite of their relative small production when compared to the three major general purpose polymers, the engineering plastics are of prime importance. An unprecedented number of new polymers with unusual functional properties have been introduced recently. These products include ionic-bonded, transparent amorphous copolymers of ethylene, polyphenylene oxide, polyxylenenes, polypyrones, polysulfones, polycylamides, polyimides, and a host of heat-resistant polymers. The growth rate of the American plastics industry is at least twice as great as that of other industries, and this trend is continuing. Over 25y0 of all organic chemists and 15% of all physical chemists are concerned with polymer technology. O n a volume basis, polymer production is approaching that of steel. The use of plastics for construction is increasing and this should be a major outlet for polymer products in the near future. Approximately one third of Japan’s production of plastics is used for construction. Newsworthy applications of plastics include its use in the Sports Palace at Genoa and the domed stadium at Houston. The former was constructed from 144 reinforced panels 92 ft. in length. I n the latter, almost 4600 double skylights of cast polymethyl methacrylate 70

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have been coated with a pigmented polymer latex to reduce glare from Texas sunlight. Other plastic panel roofs were installed at the Kalamazoo Nature Center, the tennis courts at Harvard University, and a shipping terminal at New York harbor. The new accoustical shell at the San Francisco Opera House is a plastic structure. Over 100,000 sq. ft. of vinyl plastic were used to clad the walls of the Clyde Tunnel at Glasgow. The continued success of the plastic “House of Tomorrow” erected a t Disneyland in 1957, the U. S. exhibit at the Moscow Trade Fair in 1959, and the New York State and Bell System structures at the New York World’s Fair in 1964-65 has served as the inspiration for many other buildings. The new SASA vertical assembly building consists of 70,000 sq. ft. of reinforced plastic panels bonded to an aluminum grid. A one-mil. thick film of poly(viny1 fluoride) was laminated to the exterior surface for protection against weather. This type of construction requires large quantities of sealants. New reports of polyurethane and epoxy sealants are available ( I A , 2A, 4A, 5A, 7 A ) . A new mercaptan-terminated polymer for this end use has been produced. Other polysulfide caulking compositions account for a sizable share of this $25 million industry. I t has been predicted that polyurethane sealant will account for half of the $50 billion sealant market in 1968. Plastic Structures

Design engineers who are specifying almost 3 billion lb. of plastics annually as construction material are concerned about their safe use ( I B ) . A progress report on flame-retardant plastics has been published (8B) and acceptable limits for smoke density for plastics in contact with flames have been listed in building codes in San Francisco. Rigid poly(viny1 chloride) panels have been approved for structural use by building code groups in many major metropolitan areas. The Society of the Plastics Industry and the Manufacturing Chemists Association have proposed a new identification system for coding structural plastics. The urgent need for standard specifications has been recognized (ZB)and reports on this important activity are available (5B, 7OB, 12B).

New techniques have made possible the heat-forming of a two-piece sports car body from ABS copolymers using epoxy resin tools, a submarine 22 ft. long made from reinforced epoxy resins, and large castings produced by polymerization of liquid caprolactam monomer. Large glass fiber-reinforced plastic tanks and impregnated nylon collapsible tanks are no longer newsworthy. Heavy-duty polyethylene bags, which were originally used to transport fertilizer, are also being used as shipping containers for plastic molding powders. Furan-modified binders are being used as foundry core resins. Over 2 billion bottles were blow-molded from high-density polyethylene last year. PVC wine bottles are being blow-molded from sections of extruded tubing. Equipment is available for blow-molding 150-gal. capacity drums. High-strength resin mortars have been used to construct strong, thin, brick walls (gB,IIB). Structures with excellent physical properties have been obtained by reinforcing concrete with short nylon fibers (6B). Blends of expanded perlite and phenolic resin are being used to mold structural components in the U.S.S.R. Large vessels have been constructed from new composites of asbestos, glass fibers, and furan or phenolic resins (4B). Technical information on the use of plastics in outdoor service has been provided (13B). New books on engineering design of plastics (3B) and physical properties of high polymers (7B)have been published. Composites

Because they are adaptations of tests designed for metals, the validity of tests used to evaluate physical properties of reinforced plastics has been questioned (ZC). The use of values for activation energy has been proposed for predicting the properties of polyesters a t elevated temperatures (7C). Reports have been published on new investigations of stress-strain characteristics (14C) and low-temperature properties of reinforced plastics (4C, 1OC). New reviews are available on filament winding (8C, 72C, 17C, 26C), hand lay-up techniques (13C,18C, ZlC), premix molding compositions (24C)) and prepregs (15C). Recent studies have shown that visible cracks in plastic laminates are preceded by microscopic cracks which are detectable by discoloration ( I C ) at the resinglass interface (5C). Another study has shown that the interlaminar shear strength of filament composites is a function of both resin strength and composite void content (?E). Selective sizings may be used to ensure strong bonds between the glass fiber surface and all commercially available elastomers (25C). Unless there is an intimate contact between the glass and resin, the glass surfaces may be damaged by fibers rubbing against each other (27C). High-strength laminates may be obtained by removal of the adsorbed layer of water from the glass surface before application of the catalyzed resin. The production of large filament-wound rocket cases has been achieved by construction of large mandrels from bolted segments. These are removed after curing

of the composite. Tanks with diameters exceeding 50 ft. have withstood working pressure tests of 35 p.s.i. (3C). Pipes and stacks for chemical processing plants have been produced by helically winding resin-impregnated glass filaments over cylindrical shapes of poly(viny1 chloride). Impermeable pressure vessels have been fabricated by the electrodeposition of thin metal liners on the mandrel before filament winding. The surface properties of reinforced plastic structures have been improved by the use of organic fiber veils ( 7 7C). Single crystals or carborundum filament whiskers, with tensile strengths of 3 million p.s.i., are commercially available (23C). Reinforcements based on niobium, tantalum, boron, hydrous magnesia, and stainless steel fibers have also shown promise. Ordinary carbon black serves as a chain stopper for radicals produced by photochemical reactions (6C). Refractory carbon yarns have high strength and may be used to reinforce resins for ablative applications. Many reinforced injection moldable thermoplastics are available for engineering applica2OC). New information has been provided tions (E, on the use of hollow glass fibers (22C) and the joining of reinforced plastic tubes (16C). Development work is being continued on the use of cobalt-GO for curing monomers impregnated in wood. The U. S. Atomic Energy Commission plans to test this process in a wide variety of industrial applications. Plastics vs. Temperature

Characteristic high strength-to-weight ratios, good insulating properties, and excellent ablative characteristics of properly compounded filled resins ( 1 7 0 ) make plastics the obvious first choice for space age applications. Over a score of heat-resistant resins are now under investigation (200, 210). These include polyphenylene oxide ( ?70), polyquinols ( 1 8 0 ) ) polybenzimidazoles ( 140, 760, 190, 24D), polyphenylene, polyimidazo pyrolones (pyrrones), bis(imidazo1ato)metal polymers (ZD), polyaromatic hydrazides (6D), polyoxodiazoles (50))quinoid polymers (120)) polydiphenylthiazolothiazoles ( 4 0 ) ) polycarboranes (9D), 8-hydroxy quinolineformaldehyde polymers (30), pyrolyzed polyacrylonitrile, poly(2,b-naphthalene dicarboxylate), and polyimides (80, 100, 150, 230). The present use of the latter polymer amounts to less than onehalf million pounds, but it has been predicted its use as fiber and enamel will exceed 10 million pounds in 1970. Asbestos-reinforced silicone resin laminates are satisfactory for service at 200-400' C. (220). Polyester laminates are serviceable at temperatures slightly below this range (ID).These products should be tested at the anticipated service temperature (250). Aromatic amide and imide polymers have been tested a t 650' F. (70). Interest continues in polymers of phosphonitrilic chloride AUTHOR D r . R. B.Seymour is Associate Chairman of the Department of Chemistry at the University of Houston. He is recognized as a plastics pioneer and has written the annual review f o r INDUSTRIAL & ENGINEERING CHEMISTRY since 1950. VOL. 5 7

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and blends of this product with phenolic resins. A new book on inorganic pol)-mers has been published (730). Plastics vs. Flame

Blends of polystyrene and halogen compounds have been made self-extinguishing by the addition of synergistic compounds and free radical initiators (3E, 5E, 6 E ) . Flame-resistant polyurethane foams have been produced by the addition of phosphorus or chlorine compound (9E, 70E) or by the use of bromotoluene diisocyanate as a reactant ( 8 E ) . Self-extinguishing polyester resins have been prepared by the addition of antimony oxide or halogen compounds ( ? E ) . Epoxy resins cured with chlorendic anhydride have shown promise as flame-resistant materials ( 7 ? E ) , The subject of dame retardancy has been surveyed (4E, 7E) and a new flammability test has been proposed (2E). Plastics vs. Environment

Recent studies have included the effects of weathering (8F, 37F), of photochemical degradation (73F, 75F),of oxidative degradation (77l7, 34F), and of microorganisms (35F) on plastics. The effect of heat on degradation of polyfluorocarbons ( 7 F ) and thermosetting resins (24F) has been studied and a relationship between structure and resistance to environmental attack has been suggested (16F). Other investigations include the effect of light on poly(viny1 chloride) (22F) and the role of pigments in stabilization of polypropylene (36F). A mechanism for the degradation of unsaturated polymers has been proposed (ZF). New data on the effects of exposure of reinforced plastics to sea water (32F) and corrosives (6F, 14F, 25F, 37F) have been published. Other investigations include the chemical resistance of polyesters obtained from succinic acid (33F) and hydrogenated bisphenol ( 2 1 F ) . Several papers review the corrosion resistance of plastics (QF,72F: 27F) and polyfluorocarbons (?OF, 29F). Corrosion-resistant equipment has been produced by the impregnation of graphite with resins (TF, 23F). A “boiling water index” based on extractives from reinforced plastics has been used as a test for these materials (18F). A relationship between depth of acid penetration and thickness of plastics was developed (SF). Per cent weight change and change in flexural strength have been used to predict long-term performance of reinforced plastics in corrosive environments (4F, 7 IF). This relationship has been employed to investigate the effect of variables on the chemical resistance of plastic laminates (3OF). A modified Fraas brittle point test has been suggested for studying the progressive changes in asphalt during weathering (2OF). Standard ASTM D-54B immersion tests are acceptable for screening but reinforced plastics should be tested on a bending jig to determine their usefulness in corrosive environments (3F). Radioactive sulfur in sulfuric acid has been used to study the penetration of corrosives in vinyl coatings on metals. T h e impulses counted by a beta particle scintillator are proportional to the activity of the corrosive, and inversely proportional to the film thickness. New nondestructive 72

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tests for plastics have been provided (28F). New graphite-filled modified phenolic resins have been used to fabricate chemical process equipment (79F). The use of plastics for fabrication of chemical apparatus has been surveyed (26F). Sheets and Film

Self-sealing irradiated polyethylene film with semiconducting properties is available. General purpose polyethylene film has been used as a liner to reduce water loss in over 100 reservoirs in the Imperial Valley. Black polyethylene film used as a mulch on large acreages in Arizona has increased yields and hastened maturity of lettuce crops. A stream of oxygen atoms from a plasma jet has improved printability of polyethylene film, Sheet with uniform cylindrical holes has been produced by irradiation of polyethylene film. New information has been provided on poly (vinyl chloride) film and sheet (7G, 6G,14G). A 2-mil thick poly(viny1 chloride) film has been used to line thickening tanks over 200 ft. in diameter a t a West Coast copper plant. Filled plasticized poly(viny1 chloride) sheet has been used to dampen vibrations. The relationship of index of refraction and other film properties has been investigated (73G). New techniques for studying gas permeability of film and sheet have been suggested (5G, 7G, 75G). New information is available on the use of ultrasonics for joining poly(viny1 chloride) sheet (gG, 72G). Tests have been developed for estimating the strength of joints in plastic film (77G) and the adhesion of polyfluorocarbon tank linings (76G). Thin silicone films have been used as selective semipermeable membranes for gases in the presence of liquid water. Reviews have been published on the use of poly(viny1 chloride) sheet for packaging (8G) and corrosion-resistant applications (ZG, IOG). A new SPI handbook on welding and fabrication of thermoplastics has been published. Thick sheets of polyethylene are used for neutron shielding. A superior writing and printing paper has been produced from filled polypropylene. The addition of selected fillers has improved the resistance of butyl rubber to weathering (4G). Simple techniques for the identification of plastic films have been developed (3G). Polyethylene sheet with thickness u p to 3 / 4 in. is available in 75-in. widths. Protective Coatings

I n spite of competition from surfaces that do not require additional protection, the sales of industrial finishes and coatings continue a t an annual rate in excess of $2 billion. Several near reviews on this subject are available ( I H , 6H, 12”). Polyethylene-coated cartons account for the major share of the 24 billion milk containers produced in 1964. A 30-year life span has been predicted for thin polyvinylidene fluoride coatings, Interest continues in heatresistant amide-imide wire coatings and intumescent coatings. Mixtures of melamine phosphate and organophosphorus compounds in pentaerythritol resin have been proposed for the latter application.

New emphasis has been placed on the use of good engineering principles (5H, I i”)and properly designed test panels (2H) for the selection of coatings. The results of immersion and weathering tests on thick polyester coatings have been published (3H). The durability of acrylic lacquers has been improved by blending w i t t polyacrylamide. Air-drying epoxy-modified acrylic coatings and a variety of temperatureresistant coatings for space age applications are available. Many different polymers in finely divided form may be applied as electrostatically charged particles on mildly conductive surfaces. Coatings 20 mils thick have been applied as powders and subsequently fused with heat (9H). New reports on fluidized bed techniques ( 7 H ) and coating technology (70H) have been published. Three methods for applying powdered poly(viny1 chloride) on steel have been compared (4H, 8H). Plastic Pipe

Over 400 million feet of plastic pipe were installed in this country in 1964. Polyethylene, poly(viny1 chloride), and ABS accounted for over 90% of this volume. It has been estimated that about 70% of plastic pipe used here bears the N.S.F. seal of approval. Because of excellent performance of plastic pipe systems in rural areas, the Farmers Home Administration has financed more than 10,000 miles of plastic pipe since 1960. Over 100 miles of PVC pipe with solvent-cemented joints were installed in a new water distribution system in Green Valley near San Antonio, Tex. New commercial standards have been established for PVC and ABS water pipe and drain waste, and vent pipe. The latter use (DWV pipe) has been approved by the Building Officials Conference of America. One contractor saved over $30,000 by installing DWV pipe in 500 new homes in Key West. Information on potable water systems ( I J ) , commercial standards (5J),nondestructive tests ( 7 I J ) , and stress rupture tests (4J, 8 J ) has been provided. The migration of lead in unapproved lead-stabilized PVC water pipe has been investigated (6J). Over 7000 miles of plastic pipe installed for gas transmission during the past 10 years are still in service. A one-piece polyethylene tube almost 3 miles in length was extruded on shore and floated across Lake Molar in Sweden. A 1500-foot long polypropylene. insert was used to repair a leaking metal petroleum line under the Houston ship channel, Interest in plastic-lined steel and filament-wound reinforced plastic pipe continues. A 20,000-foot epoxylined and polyethylene-coated steel fuel pipe was installed at the Pittsburgh Airport. Reviews have been published on reinforced plastic pipe (ZJ, 7 J , IOJ), acetal pipe (3.4, and polvyinyl dichloride pipe ( 9 J ) . Cellular Plastics

Over 300 million pounds of cellular plastics were produced last year and it is anticipated that this volume will double by 1969. Expandable polystyrene mixed with adhesives may be blown directly into packages containing fragile articles.

Foamed-in-place polyurethanes were used to fill 150 thousand cubic feet of space and thus provide buoyancy to a platform dismantled in the Atlantic Ocean. Many wine tanks (2K) and oil refinery storage tanks ( 4 K ) have been insulated by use of rigid polyurethane foams. The relationship between properties and structure of urethanes has been investigated (8K, I4K). A bibliography on this correlation is available in the ACS Rubber Division Library a t the University of Akron. New treatises on polyurethane technology have been published (73K, 75K). I t has been shown that methyl polyurethanes have less tendency to yellow than unsubstituted polymers ( I K ) . The chlorine content of flame-resistant foams has been reduced by the addition of free radical initiators (70K). The rate of rise of foam has been used to evaluate catalytic activity (16K). Styrene-acrylonitrile copolymer foams are resistant to gasoline (9K). Trimerization of isocyanate-terminated prepolymer or the addition of trialkoxyboroxine produces heat-resistant foams (5K,12K). PVC plastisols have been used to produce open-cell flexible foams ( 7 K ) . Reviews on the production of expanded polystyrene are available (3K, 77K). New uses of phenolic foams in the building industry have been reported (6K). Progress in Polymer Science

One of the newer resins, polyphenylene oxide, is produced by oxidative coupling of 2,6-dimethylphenol using oxygen in the presence of an amine complex of copper. This injection-moldable polymer has excellent high-temperature and electrical properties (7L). Continuous thin coatings have been produced by vapor phase pyrolysis of xylene or p-chloroxylene. The dimer produced is sublimed and cooled to obtain a monomer which polymerizes to poly@,-xylenene). This product and its chloro derivative have excellent dielectric properties. Transparent polysulfones produced by the condensation of bisphenol A and dichlorodiphenyl sulfone have excellent resistance to thermal oxidation and may be injection molded (IOL). A new series of sodium-catalyzed butadiene styrene copolymers (8L) may be easily transfer molded. Phenoxy resins have shown considerable promise for blowmolded containers. Interest in polypropylene oxide continues (2L). A product with excellent properties is obtained by the addition of carbon black (6L). Laser light has been employed to initiate the polymerization of styrene and vinylacetate at low temperatures. New information has been supplied on static charge buildup (3L, 9L), photodegradation (4L), stabilizers ( I L ) , and plastic modifiers ( 7 IL). Pyrolytic gas chromatography has been used to identify a large number of polymers (5L). Thermosetting Plastics

The availability of automatic transfer molding techniques has increased the use of thermosetting molding compositions (3.44, 6 M ) . Over 800 million pounds of VOL. 5 7

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phenolic resins were produced in 1964. Infrared spectrophotometry (25M) and proton magnetic resonance ( 2 7 M ) have been used to study phenol formaldehyde resins. New information on the oxidative degradation of phenolic resins is available ( 9 M ) . Approximately 100 million pounds of epoxy resins were produced in 1964. The technology of these resins (70M,26M) and their use in the construction industry (52M) have been reviewed. Boron trifluoride-amine adducts (27M) and combinations of tertiary amines and anhydrides ( 14M) have been recommended as curing agents for epoxy resins. Infrared spectrophotometry ( 7 M ) and changes in electrical properties (18M) have been used to determine the extent of cure in epoxy resin compositions. Infrared spectrophotometry has also been used to characterize bromine-containing epoxy resins ( 7 5 M ) . The effect of size of filler on properties ( 7 2 M ) and the chemical resistance of epoxy resins have been studied ( 7 6 M ) . New technical information on the allylic ( 2 3 M ) and maleic anhydride types of polyester resins ( I M , 2 M ) is available. The relationship of structure to properties of polyesters has been investigated (8M, 19M). Polyester resins have been characterized by column chromatography (4M),gas chromatography ( 7 3 i M ) , and N M R techniques ( 2 2 M ) . Xew data are available on the chemical resistance of these resins (17M, 77M,24M). Production techniques have been discussed (20M). Approximately 250 million pounds of unsaturated polyester resins were produced last year. Thermoplastics

In spite of the increased interest in thermosetting plastics, thermoplastics account for over 75y0 of the annual production of plastics in the United States and Canada. The annual production of styrene plastics in the U. S. should exceed 2 billion pounds by 1966. Vinyl polymers are already being produced at this rate, and polyolefin production approached 3 billion lb. last year. Polyolefins. Low-density polyethylene accounts for 70Yc of all polyolefin production. However, the use of the high-density product increased by 35YC in 1964. The increase in use of polypropylene was almost 60%. I n 1964, 600 million pounds of high-density polyethylene and 200 million pounds of polypropylene were produced. Finely divided polyolefin powders may be dispersed in liquids to yield highly concentrated mixtures. A review has been published on the development of highdensity polyolefins (79.T). NMR studies have shown that most of the change from cis to trans isomer occurs in the early stages of polymerization of ethylene (&Y). A recent study has shown that the stress cracking of polyethylene depends on the wetting tension of the corrosive and the degree of swelling of the polymer ( 77LY). Several new investigations of the irradiation of polyethylene have been reported (3>lT,71Y, 8 s ) . Deuterium tagging has been used to study the mechanism of thermal decomposition of polyolefins ( 2 F ) . Polyethylene blends have been analyzed by DTA techniques (7&Y). 74

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Alkylated phenol formaldehyde polymers have been used to increase the tack of ethylene-propylene terpolymers (EPT). Infrared studies have shown that this product contains fewer double bonds than butyl rubber ( I O N ) . This terpolymer now accounts for 2OY0 of all synthetic elastomer production (72N, 76,li). Products with excellent resistance to ozone have been obtained by the copolymerization of ethylene with butadiene. Many hot-melt wax compositions used for coatings contain low-molecular weight copolymers of ethylene and vinyl acetate. The higher molecular weight copolymers are stable to ultraviolet light and are used for the production of flexible film. Oil-resistant elastomers are obtained by the copolymerization of ethylene and acrylic esters. Transparent products are obtained when ethylene is copolymerized with minor amounts of acrylic or methacrylic acid. Salts formed with sodium, potassium, magnesium, or zinc have superior resistance to solvents and crazing (?.Y2 ISLV). A review of the polypropylene industry has been published (Zit‘) and the relationship between melting point and molecular weight of isotactic polypropylene has been investigated (73S). A digital readout apparatus attached to a high-resolution infrared spectrophotometer has been used to calculate the stereoregularity of polypropylene (9-2’). Methyl acrylate has been grafted on peroxidized polypropylene ( 7 4 2 ’ ) . DTA data for propylene-styrene copolymers are available (6‘V). Electron spin resonance (5iY) and differential thermal analysis ( I IlV) have been used to study degradation of polypropylene. Poly(4-methyl pentene-1)) which has an unusually low specific gravity of 0.83, may be steam sterilized. Vinyl Plastics. The large increase in the production of vinyl plastics in this country was exceeded on a percentage basis by unprecedented growth of the vinyl plastic industry in several other nations. The anticipated demand in Japan is greater than that country’s 47,000 metric ton capacity. Approximately 300 million pounds of vinyl plastics were produced in the United Kingdom in 1964. The 25 million pound production of rigid vinyl plastics in the United States accounts for less than 2Yc of the total but this phase of the industry is growing rapidly. Degradation of rigid PVC has been followed by observing the “yellow index” with, blue and green filters in a differential colorimeter (6P). New processes for the economical production of monomer by oxychlorination (9P), new advances in compounding (7P, 14P), and new applications of modern instrumental techniques to the study of vinyl resins have assured continued growth of this 2 billion pound plastic. Some of the new information available includes the identification and evaluation of stabilizers (SP, IOP, 76P) and plasticizers (2P), including study of the relationship between performance and structure of plasticizer (78P), The absorption of plasticizer is a function of the structure of the PVC granules ( I P ) . Products with controlled hardness have been obtained by adding small amounts of polymerizable plasticizers to plastisols.

Plasticizer efficiency has been characterized by fusion rates during mastication (77P). Both chlorinated polyethylene (75P) and nitrile rubber (3P) have been used as modifiers for PVC. Plasticizers in both filled and unfilled compositions have been characterized by N M R techniques (4P, 72P). Solubility has been reduced and dye affinity has been increased when ultraviolet light has been used to graft methacrylic acid on PVC (73P). Additional general information on plasticizers has also been published (8P, 1 IP). Styrene Plastics. Polystyrene and styrene copolymer plastics are being produced at the rate of 150 million pounds a month in this country. Styrene copolymer elastomers still account for over 50% of the synthetic rubber production. Approximately 15y0of the 2-billion pound styrene plastic market consists of products containing acrylonitrile copolymers. The uses of styreneacrylonitrile copolymers have been reviewed (44) and a new book on ABS plastics has been published ( 1 Q ) . New information is available on physical properties (SQ), antistatic treatment (3Q, S Q ) , and the relationship of melt flow and molecular weight distribution of polystyrene (24). New stabilizers which reduce the tendency for yellowing of polystyrene sheets in the presence of light are available. A 1-mil thick polyvinyl fluoride film has also been used for this purpose. New data also have been published on the oxidative degradation of styrene polymers (7Q). Polyfluorocarbons. The annual production of fluorine-containing polymers in the United States is less than 25 million pounds. However, these versatile engineering plastics are of sufficient importance to maintain the production interests of four major corporations. New reports are available on uses of polyfluorocarbons in chemical processing plants (ZR, 77R, 72R), as gaskets ( 3 R ) , for electrical applications (73R),and for bearings (IOR). The useful life of steel bearings has been increased 10 times by coating with polytetrafluoroethylene. Many diverse uses of these polymers were reviewed at a conference of the Fluorocarbons Division of SPI. Graphite-filled polymers have a low coefficient of expansion and are suitable for chemical process equipment. Polymers of a,p, P-trifluorostyrene ; perfluoroisobutylene ; perfluoroazomethine ; perfluorophenyl ether (9R); vinylidene fluoride (4R); and other fluorinecontaining monomers (7R) have been investigated. Strong bonds between polyfluorocarbons and epoxy resins have been obtained a t specific temperatures. Polyfluorocarbon film has been used as a flexible light source. New analytical data on polyfluorocarbons are based on mass spectrometry ( 5 R ) , infrared spectrophotometry (14R), and DTA (811). New information on the irradiation of fluorine-containing polymers has been published (7R, 6 R ) . Polyamides. The total annual production of synthetic polyamides in the United States is about 750 million pounds. Most of the product is nylon-6,b fiber. Recent studies have demonstrated the relationship of solubility and the ratio of methylene and amide groups, pH, and the degree of crystallinity in nylon (58).

The effects of light (ZS),water vapor, and chemicals on nylons have been studied (IS,3s). New information is available on poly(l,4-cyclohexylene dimethylene subaramide) ; poly (m-xylylene adipamide) (63); and piperazine polyamide (48). Acrylates. New, tough acrylic polymers have been proposed as engineering plastics (727, Melamine resins have been added to obtain cross-linked acrylic plastics ( 7 2 T ) . A new report has been issued on cyanoacrylic adhesives ( 7 T ). Large quantities of acrylonitrile are now being produced from ammonia and propylene, Polyacrylic anhydride ( 6 T ) , polycyanothioalkyl acrylates ( 7 7 T ) , tertiary butyl acrylate-ethylene copolymers (577, and methylmethacrylate-maleic anhydride copolymers ( 9 T ) have been described. New data have been published on photolysis (ZT,8 T ) , pyrolytic gas chromatography (47‘) lOT), and infrared spectrophotometry ( 3 T ) of polyacrylates and their degradation products. Miscellaneous Polymers

A bibliography on relation of structure to properties of polyurethanes has been added to the Library of the Rubber Division of the American Chemical Society (74U). Other new technical information is available on casting compounds (3U, lZU, 76U), missile applications (20U), x-ray diffraction studies ( I U ) , infrared spectrophotometry, and investigations of the thermal degradation of urethane polymers (73U). The reaction product of dipropylene glycol and toluene diisocyanate has superior physical properties (4U). Acetal polymers which are described as engineering plastics are being produced a t the rate of 50 million pounds a year. Polymers of acetaldehyde (78U), chloroacetaldehyde ( 7 U ) , methylmethacrylate-maleic anhydride copolymers ( 9 T ) ,and other new copolymers have been investigated (8U, 1QU). T h e pyrolysis of acetal polymers has been studied (17U). A new book (75U)and information on the stability (QU) and pyrolytic studies (5U) of polycarbonates are available. Some of the other reports on new products and techniques include fundamentals of polymerization (ZU), identification of polymers ( 6 U ) , tailor-making of plastics (70U), and the development of engineering plastics ( 7 7 V ) . REFERENCES General Information (1A) Amstock, J. S., Adhesiuer Age 7 ( l l ) , 36 (1964). (2A) Fosgate, C. M . , Natl. Acad. Sci.-Natl. Res. Council Publ. N o . 1006, 115 (1962-63). (3A) Kline, G. M., M o d . Plastics 42 (6), 117 (1965). (4A) LeFave, G . M., Gamero, R., Hayashi, F. Y., Natl. Acad. Sei-Natl. Res. Council Publ. No. 1006, 93 (1962-63). (5A) Morris, L., Mater. Protection 3 (7), 30 (1964). (6A) Smoluk, G. R., M o d . Plastics 42 (6), 97 (1965). (7A) Wittenwyler, C. V., Natl. Acad. Sci.-Natl. Res. Council Publ. NO. 1006, 131 (1962-63). Plastic Stpuctures (1B) Aston, L.A., Plastics Inst. (London) Trans. J.32, 27 (1964). (2B) Atkinson, H. E., M a t e r . Protection 3 (6), 16 (1964). (3B) Baer, E,, “Engineering Design for Plastics,” Reinhold, New York, 1964. (4B)Barton, H.D . , IND. ENC.CHEM.5 6 (7), 66 (1964). (5B) Davis, J. W., Sac. Plastics Engrs. J. 20, 601 (1964). (6B) Goldfein, S., Mod. Plastics 42 (E), 156 (1965).

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(7B) Gordon, M., “High Poiymcrs, Structure and Physical Properties,” AddisonWesley, Reading, Mass., 1964. (8B) Hauck, J. E.: Muter. Design Eng. 6 0 ( l l ) , 83 (1964). (9B) Hill, A. A,, Adhesines Age 7 (7), 31 (1964). (10B) Kline, G. M., Mod. Plastics 4 2 (91, 176 (1965). (11B) Kubisiak, D. P., Eash, R. D., Hill: A. A , Western Plostics 12 (2), 23 (1965). (12B) Peters, R . I., Mater. Protection 3 (8): 16 (1964). ( 1 3 ~ )Seymour, R . B., Plartics World 22 (6), 48 (1964). Composites (1C) Alt, B., Kunststofe 51 ( 7 ) , 397 (1964). (2C) Barnet, F. R., Prosen, S . P., Mater. Protection 3 (6), 32 (1964). (3C) Bell, R . L., Young, E. C., Chem. Eng. Progr. 61 ( 4 > > 57 (1965). (4C) Brink, N. O., Sot. Plustics E n p . J.20, 1123 (1964). (5C) Broutman, L. J., M o d . Plartics 4 2 (8), 143 (1965). (6C) Drogin, I., Soc. Plastics Engrs. J . 21, 248, 371 (1965). ( 7 C ) Filson, A. C., fhid., 20, 459 (1964). ( 8 C ) Foerster, A. F., Boller, T. J,,Soc. Plastics Engrs. T r a n s . 4 (4), 102 (1964). (9C) Further, W.F., Can. J.Chem. Eng. 4 2 (4), 77 (1964). (10C) Hertz, J.: Soc. Plastics Engrs. J . 21, 181 (1965). (1112) Hoehn, R., Heling, W., ReinforcedP/astics4 (2), 12 (1965). (12C) Howard, J . S., Prod. Eng. 35, 102 (1964). (13C) Knowies, P., Rubber Plnstics Age 45 (5), 509 (1964). Soc. Plastics Engrs. J.20, 2.0, 1031 (1964). (14C) Krolikowski, W.; (15C) Laue, E. W., Plnstaerarheiter 15 ( 9 ) , 527 (1964). (16C) Lauterback, T . , Chem. Eng. 17 (16), 124 (1964). (17C) Martenson, J. A,, M o d . PlosticJ42 (9): 167 (1965). (18C) Ogden, G., Brit. Plastics 37 (3), 138 (1964). (19C) Petker, T., SOC.P/nstics Engrs. T r a n s . 5 , 49 (1965). (20C) Plodek, 0. J., Rein/orcedPlostirs4 (1): 28 (1965). (21C) Rosato, D . V.,Grove, C. S., Ihid., 3 (4): 10 (1964). (22C) Sicfert, R . F., Ibid., 4 ( l ) , 22 (1965). (23C) Surton, W. H., Rosen, B. TT., Flom, D. G., Soc. Plnstics Engrs. J. 20, 1203 (1964). (24C) Tochtermann, W.: Plostuerorheiter 15 (9), 535 (1964). PROD.RES.DEVELOP. (25C) Vanderbilt, B. M., Clayton, R. E., 1x0. ENG.CHEM. 4 , 18 (1965). (26C) Young, E. C., Mech. E n q , 85 (10): 36 (1964). (27C) Zisman, W. A,, IND. ENG.CHEM.57 ( l ) , 26 (1965). Plastics os. Temperatures (ID) Boller, K . H., U. S . Dept. Cornm. Office Tech. Serv. Refit. AD 606767 (1964). (2D) Brown, G. P., Aftergut, S.: J.Polymer Sci. 2, 1839 (1964). (3D) Degeiso, R . C., Donoruma, L. G., Tomic, E. A,, J.Appl. Polymer Sci. 9 (2), 41 1 (1965). (4D) Fox, C. J., J.Poly S a . 2 A , 267 (1964). (5D) Frazer, A . H., Sweeney, TV.,M’allenberger, F. T., Ihid., p. 1157. (6D) Frazer, A . H., Wallenberger, F. T., Ihid.. p. 1147. (7D) Freeman, J. H., Frost, L. W., et ai., SOC.Plastics En,qrs. T m n s . 5, 75 (1965). (8D) Frost,L. W.: Bower, G. M ,ACSDiue. PoljmerChem. Reprints4 ( l ) , 357 (1963). (9D) Green, 3.: Mayes, N., et nl., J . Polymer Sci. 2 A , 3113 (1964). (1OD) Heacock, J. F., Berr, C. E., Sot. Plnrtics Engrs. Trons. 5 , 105 (1965). ( I l D ) Hoyt, H. E., Halpern, B. D., e t ai., J.Appl. Polymer Sei. 8 , 1633 (1964). (12D) H u n t , S. E., Lindsey, A. S., Chem. Ind. (London) 32, 1272 (1964). 113D) Hunter, D . N., “Inorganic Polymer,” Wiley, New York. 1964. (14D) Iwakura, Y., Uno, K., Iwai, Y., J . Polymer Sci. 2, 2605 (1964). (1 5D) Korshak, V. V., Frunze, T. M., “Synthetic Heterchain Polyimides,” Davey, New York, 1964. (16D) Korshak, V . V., Frunze, T. M,, Izyneev, A. A . , 7.2V Akad. Nauk. USSR Ser. Khim. 1964 ( l l ) , p. 2104. (17D) Lurie, R., Gregiev, S., Levine, P.: Chem. Eng. Progr. 60 (2), 62 (1964). (l8D) Marvel, C. S., SOC.Plastics Engrs. Trans. 5 , 25 (1965). (19D) Plummer, L., Marvel, C. S., J.Polymer Sci. 2, 2559 (1964). (20D) Reichherzer, R., Kunststofe-Plastics 11 ( l ) , 10 (1 964). (21D) Seymour, R . B., Plastics in Austrnlin 16 (l), 15 (1965). (22D) Taylor, W., SOC.Ploriics Engrr. J.20, 624 (1964). (23D) T o d d , K. W.? Wolf?, F. A,, et ai., Machine Design 36,228 (1964). (24D) WrasidIo, W., Levine, H. H., J . Polymer Sci. 2, 4795 (1964). (25D) Younp, M. G., Prod. Eng. 35 (15), 67 (1964). ~I

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