Bakelite

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Bakelite
3-D Structure of Bakelite.png
Identifiers
3D model (JSmol)
ChemSpider
  • none
Properties
(C6H6O·CH2OH)n
Molar mass Variable
AppearanceBrown solid
Density 1.3 g/cm3 [1]
Thermal conductivity 0.2 W/(m·K) [1]
1.63 [2]
Thermochemistry
0.92 kJ/(kg·K) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Bakelite ( /ˈbkəlt/ BAY-kəl-eyet; sometimes spelled Baekelite) or polyoxybenzylmethylenglycolanhydride was the first plastic made from synthetic components. It is a thermosetting phenol formaldehyde resin, formed from a condensation reaction of phenol with formaldehyde. It was developed by the Belgian-American chemist Leo Baekeland in Yonkers, New York, in 1907.

Plastic material of a wide range of synthetic or semi-synthetic organic solids

Plastic is material consisting of any of a wide range of synthetic or semi-synthetic organic compounds that are malleable and so can be molded into solid objects.

Thermosetting polymer polymer material that irreversibly cures

A thermosetting polymer, resin, or plastic, often called a thermoset, is a polymer that is irreversibly hardened by curing from a soft solid or viscous liquid prepolymer or resin. Curing is induced by heat or suitable radiation and may be promoted by high pressure, or mixing with a catalyst. It results in chemical reactions that create extensive cross-linking between polymer chains to produce an infusible and insoluble polymer network.

Contents

Bakelite was patented on December 7, 1909. The creation of a synthetic plastic was revolutionary for its electrical nonconductivity and heat-resistant properties in electrical insulators, radio and telephone casings and such diverse products as kitchenware, jewelry, pipe stems, children's toys, and firearms.

In recent years the "retro" appeal of old Bakelite products has made them collectible. [3]

Bakelite was designated a National Historic Chemical Landmark on November 9, 1993, by the American Chemical Society in recognition of its significance as the world's first synthetic plastic. [4]

National Historic Chemical Landmarks

The National Historic Chemical Landmarks program was launched by the American Chemical Society in 1992 to recognize significant achievements in the history of chemistry and related professions. The program celebrates the centrality of chemistry. The designation of such generative achievements in the history of chemistry demonstrates how chemists have benefited society by fulfilling the ACS vision: Improving people's lives through the transforming power of chemistry. The program occasionally designates International Historic Chemical Landmarks to commemorate "chemists and chemistry from around the world that have had a major impact in the United States".

American Chemical Society American scientific society

The American Chemical Society (ACS) is a scientific society based in the United States that supports scientific inquiry in the field of chemistry. Founded in 1876 at New York University, the ACS currently has nearly 157,000 members at all degree levels and in all fields of chemistry, chemical engineering, and related fields. It is the world's largest scientific society by membership. The ACS is a 501(c)(3) non-profit organization and holds a congressional charter under Title 36 of the United States Code. Its headquarters are located in Washington, D.C., and it has a large concentration of staff in Columbus, Ohio.

History

Baekeland was already wealthy due to his invention of Velox photographic paper when he began to investigate the reactions of phenol and formaldehyde in his home laboratory. Chemists had begun to recognize that many natural resins and fibers were polymers. Baekeland's initial intent was to find a replacement for shellac, a material in limited supply because it was made naturally from the excretion of lac insects (specifically Kerria lacca ). Baekeland produced a soluble phenol-formaldehyde shellac called "Novolak", but it was not a market success. [4]

Phenol Chemical compound

Phenol is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group (−C6H5) bonded to a hydroxy group (−OH). It is mildly acidic and requires careful handling due to its propensity for causing chemical burns.

Formaldehyde Widely used toxic organic compound

Formaldehyde (systematic name methanal) is a naturally occurring organic compound with the formula CH2O (H−CHO). It is the simplest of the aldehydes (R−CHO). The common name of this substance comes from its similarity and relation to formic acid.

Polymer Substance composed of macromolecules with repeating structural units

A polymer is a large molecule, or macromolecule, composed of many repeated subunits. Due to their broad range of properties, both synthetic and natural polymers play essential and ubiquitous roles in everyday life. Polymers range from familiar synthetic plastics such as polystyrene to natural biopolymers such as DNA and proteins that are fundamental to biological structure and function. Polymers, both natural and synthetic, are created via polymerization of many small molecules, known as monomers. Their consequently large molecular mass, relative to small molecule compounds, produces unique physical properties including toughness, viscoelasticity, and a tendency to form glasses and semicrystalline structures rather than crystals. The terms polymer and resin are often synonymous with plastic.

Baekeland then began experimenting on strengthening wood by impregnating it with a synthetic resin, rather than coating it. [4] By controlling the pressure and temperature applied to phenol and formaldehyde, Baekeland produced a hard moldable material that he named "Bakelite", [5] [6] after himself. It was the first synthetic thermosetting plastic produced, and Baekeland speculated on "the thousand and one ... articles" it could be used to make. [7] :58–59 Baekeland considered the possibilities of using a wide variety of filling materials, including cotton, powdered bronze, and slate dust, but was most successful with wood and asbestos fibers. [7]

Baekeland filed a substantial number of patents in the area. [4] Bakelite, his "method of making insoluble products of phenol and formaldehyde," was filed on July 13, 1907, and granted on December 7, 1909. [8] Baekeland also filed for patent protection in other countries, including Belgium, Canada, Denmark, Hungary, Japan, Mexico, Russia, and Spain. [9] He announced his invention at a meeting of the American Chemical Society on February 5, 1909. [10]

The first semi-commercial Bakelizer, from Baekeland's laboratory, 1935 First Semi-commercial Bakelizer 1935 Bakelite Review Silver Anniversary p6.tif
The first semi-commercial Bakelizer, from Baekeland's laboratory, 1935

Baekeland started semi-commercial production of his new material in his home laboratory, marketing it as a material for electrical insulators. By 1910, he was producing enough material to justify expansion. He formed the General Bakelite Company as a U.S. company to manufacture and market his new industrial material. He also made overseas connections to produce materials in other countries. [4]

Bijker gives a detailed discussion of the development of Bakelite and the Bakelite company's production of various applications of materials. [11] As of 1911, the company's main focus was laminating varnish, whose sales volume vastly outperformed both molding material and cast resin. By 1912, molding material was gaining ground, but its sales volume for the company did not exceed that of laminating varnish until the 1930s.

As the sales figures also show, the Bakelite Company produced "transparent" cast resin (which did not include filler) for a small ongoing market during the 1910s and 1920s. [11] :172–174 Blocks or rods of cast resin, also known as "artificial amber", were machined and carved to create items such as pipe stems, cigarette holders and jewelry. [11] [12] However, the demand for molded plastics led the Bakelite company to concentrate on molding, rather than concentrating on cast solid resins. [11] :172–174

The Bakelite Corporation was formed in 1922 after patent litigation favorable to Baekeland, from a merger of three companies: Baekeland's General Bakelite Company; the Condensite Company, founded by J.W. Aylesworth; and the Redmanol Chemical Products Company, founded by Lawrence V. Redman. [13] Under director of advertising and public relations Allan Brown, who came to Bakelite from Condensite, Bakelite was aggressively marketed as "the material of a thousand uses". [7] :58–59 [14] A filing for a trademark featuring the letter B above the mathematical symbol for infinity was made August 25, 1925, and claimed the mark was in use as of December 1, 1924. A wide variety of uses were listed in their trademark applications. [15]

Color chart for Bakelite "jewel" quality colors (cast resin or "Clear Material"), 1924 Bakelite color chart 1924 Gifts to Treasure Embed Art Company Jewel only.tif
Color chart for Bakelite "jewel" quality colors (cast resin or "Clear Material"), 1924

The first issue of Plastics magazine, October 1925, featured Bakelite on its cover, and included the article "Bakelite – What It Is" by Allan Brown. The range of colors available included "black, brown, red, yellow, green, gray, blue, and blends of two or more of these". [16] The article emphasized that Bakelite came in various forms. "Bakelite is manufactured in several forms to suit varying requirements. In all these forms the fundamental basis is the initial Bakelite resin. This variety includes clear material, for jewelry, smokers' articles, etc.; cement, using in sealing electric light bulbs in metal bases; varnishes, for impregnating electric coils, etc.; lacquers, for protecting the surface of hardware; enamels, for giving resistive coating to industrial equipment; Laminated Bakelite, used for silent gears and insulation; and molding material, from which are formed innumerable articles of utility and beauty. The molding material is prepared ordinarily by the impregnation of cellulose substances with the initial 'uncured' resin." [14] :17 In a 1925 report, the United States Tariff Commission hailed the commercial manufacture of synthetic phenolic resin as "distinctly an American achievement", and noted that "the publication of figures, however, would be a virtual disclosure of the production of an individual company". [17]

In England, Bakelite Limited, a merger of three British phenol formaldehyde resin suppliers (Damard Lacquer Company Limited of Birmingham, Mouldensite Limited of Darley Dale and Redmanol Chemical Products Company of London), was formed in 1926. A new Bakelite factory opened in Tyseley, Birmingham, around 1928. [18] It was demolished in 1998.

A new factory opened in Bound Brook, New Jersey, in 1931. [7] :75

In 1939, the companies were acquired by Union Carbide and Carbon Corporation. In 2005, Union Carbide's phenolic resin business, including the Bakelite and Bakelit registered trademarks, were assigned to Hexion Inc. On the 1st of April, 2019 Hexion filed for Chapter 11 bankruptcy.

In addition to the original Bakelite material, these companies eventually made a wide range of other products, many of which were marketed under the brand name "Bakelite plastics". These included other types of cast phenolic resins similar to Catalin, and urea-formaldehyde resins, which could be made in brighter colors than polyoxy­benzyl­methylene­glycol­anhydride. [3] [7]

Once Baekeland's heat and pressure patents expired in 1927, Bakelite Corporation faced serious competition from other companies. Because molded Bakelite incorporated fillers to give it strength, it tended to be made in concealing dark colors. [7] In 1927, beads, bangles and earrings were produced by the Catalin company, through a different process which enabled them to introduce 15 new colors. Translucent jewelry, poker chips and other items made of phenolic resins were introduced in the 1930s or 1940s by the Catalin company under the Prystal name. [19] [20] The creation of marbled phenolic resins may also be attributable to the Catalin company.

Synthesis

External video
Nuvola apps kaboodle.svg “Making Bakelite Plastic”, NileRed

Making Bakelite was a multi-stage process. It began with the heating of phenol and formaldehyde in the presence of a catalyst such as hydrochloric acid, zinc chloride, or the base ammonia. This created a liquid condensation product, referred to as Bakelite A, which was soluble in alcohol, acetone, or additional phenol. Heated further, the product became partially soluble and could still be softened by heat. Sustained heating resulted in an "insoluble hard gum". However, the high temperatures required to create this tended to cause violent foaming of the mixture, which resulted in the cooled material being porous and breakable. Baekeland's innovative step was to put his "last condensation product" into an egg-shaped "Bakelizer". By heating it under pressure, at about 150 °C (300 °F), Baekeland was able to suppress the foaming that would otherwise occur. The resulting substance was extremely hard and both infusible and insoluble. [3] :67 [7] :38–39

Compression molding

A combustion engine's spark distributor rotor made of Bakelite RotorBakelite-2.jpg
A combustion engine's spark distributor rotor made of Bakelite

Molded Bakelite forms in a condensation reaction of phenol and formaldehyde, with wood flour or asbestos fiber as a filler, under high pressure and heat in a time frame of a few minutes of curing. The result is a hard plastic material. [21]

Bakelite's molding process had a number of advantages. Bakelite resin could be provided either as powder, or as preformed partially cured slugs, increasing the speed of the casting. Thermosetting resins such as Bakelite required heat and pressure during the molding cycle, but could be removed from the molding process without being cooled, again making the molding process faster. Also, because of the smooth polished surface that resulted, Bakelite objects required less finishing. [22] Millions of parts could be duplicated quickly and relatively cheaply. [7] :42–43

Phenolic sheet

Another market for Bakelite resin was the creation of phenolic sheet materials. Phenolic sheet is a hard, dense material made by applying heat and pressure to layers of paper or glass cloth impregnated with synthetic resin. [7] :53 Paper, cotton fabrics, synthetic fabrics, glass fabrics and unwoven fabrics are all possible materials used in lamination. When heat and pressure are applied, polymerization transforms the layers into thermosetting industrial laminated plastic. [23]

Bakelite phenolic sheet is produced in many commercial grades and with various additives to meet diverse mechanical, electrical and thermal requirements. Some common types include: [24]

Properties

Ericsson Bakelite telephone, c. 1931 Ericsson bakelittelefon 1931.jpg
Ericsson Bakelite telephone, c. 1931
Bakelite letter opener c. 1920 Bakelite letter opener.jpg
Bakelite letter opener c. 1920
Bakelite radio at Bakelite museum Bakelite radio.jpg
Bakelite radio at Bakelite museum

Bakelite has a number of important properties. It can be molded very quickly, decreasing production time. Moldings are smooth, retain their shape and are resistant to heat, scratches, and destructive solvents. It is also resistant to electricity, and prized for its low conductivity. It is not flexible. [7] :44–45 [22] [25]

Phenolic resin products may swell slightly under conditions of extreme humidity or perpetual dampness. [26] When rubbed or burnt, Bakelite has a distinctive, acrid, sickly-sweet or fishy odor. [27]

Applications and uses

Old tumbler switch composed of Bakelite Old Bakelit light switches and socket.jpg
Old tumbler switch composed of Bakelite

The characteristics of Bakelite made it particularly suitable as a molding compound, an adhesive or binding agent, a varnish, and a protective coating. Bakelite was particularly suitable for the emerging electrical and automobile industries because of its extraordinarily high resistance to electricity, heat, and chemical action. [7] :44–45

The earliest commercial use of Bakelite in the electrical industry was the molding of tiny insulating bushings, made in 1908 for the Weston Electrical Instrument Corporation by Richard W. Seabury of the Boonton Rubber Company. [7] :43 [28] Bakelite was soon used for non-conducting parts of telephones, radios and other electrical devices, including bases and sockets for light bulbs and electron tubes (vacuum tubes), supports for any type of electrical components, automobile distributor caps and other insulators. [7] [29] By 1912, it was being used to make billiard balls, since its elasticity and the sound it made were similar to ivory. [30] [31]

During World War I, Bakelite was used widely, particularly in electrical systems. Important projects included the Liberty Motor, [32] the wireless telephone and radio phone, [33] and the use of micarta-bakelite propellors in the NBS-1 bomber and the DH-4B aeroplane. [34] [35]

Bakelite's availability and ease and speed of molding helped to lower the costs and increase product availability so that telephones and radios became common household consumer goods. [7] :116–117 [36] [37] It was also very important to the developing automobile industry. [38] It was soon found in myriad other consumer products ranging from pipe stems and buttons to saxophone mouthpieces, cameras, early machine guns, and appliance casings. Bakelite was also very commonly used in making molded grip panels (stocks) on handguns, submachine guns and machineguns, as well as numerous knife handles and "scales" through the first half of the 20th century. [39]

Beginning in the 1920s, it became a popular material for jewelry. [40] Designer Coco Chanel included Bakelite bracelets in her costume jewelry collections. [41] :27–29 Designers such as Elsa Schiaparelli used it for jewelry and also for specially designed dress buttons. [42] [43] Later, Diana Vreeland, editor of Vogue, was enthusiastic about Bakelite. [44] Bakelite was also used to make presentation boxes for Breitling watches. Jewelry designers such as Jorge Caicedo Montes De Oca still use vintage Bakelite materials to make designer jewelry. [45]

By 1930, designer Paul T. Frankl considered Bakelite a "Materia Nova", "expressive of our own age". [7] :107 By the 1930s, Bakelite was used for game pieces like chessmen, poker chips, [46] dominoes [47] and mahjong sets. [48] [49] Kitchenware made with Bakelite, including canisters and tableware, was promoted for its resistance to heat and to chipping. [50] [51] In the mid-1930s, Northland marketed a line of skis with a black "Ebonite" base, a coating of Bakelite. [52] [53] By 1935, it was used in solid-body electric guitars. Performers such as Jerry Byrd loved the tone of Bakelite guitars but found them difficult to keep in tune. [54]

The British children's construction toy Bayko, launched in 1933, originally used Bakelite for many of its parts, and took its name from the material.

During World War II, Bakelite was used in a variety of wartime equipment including pilot's goggles and field telephones. [55] It was also used for patriotic wartime jewelry. [56] [57] In 1943, the thermosetting phenolic resin was even considered for the manufacture of coins, due to a shortage of traditional material. Bakelite and other non-metal materials were tested for usage for the one cent coin in the US before the Mint settled on zinc-coated steel. [58] [59]

During World War II, Bakelite buttons were part of the British uniforms. They were sometimes modified to Survival, Evasion, Resistance and Escape purposes in case of capture.[ clarification needed ] "Following the introduction of BD (Battle Dress). MI9 was forced to adapt to meet the challenge of a number of different compass solutions were devised, both covert and overt. These included Bakelite buttons used in both Army (brown colored) and RAF (black) BD uniforms." [60]

In 1947, Dutch art forger Han van Meegeren was convicted of forgery, after chemist and curator Paul B. Coremans proved that a purported Vermeer contained Bakelite, which van Meegeren had used as a paint hardener. [61]

Bakelite was sometimes used as a substitute for metal in the magazine, pistol grip, fore grip, hand guard, and butt stock of firearms. The AKM and some early AK-74 rifles are frequently mistakenly identified as using Bakelite, but most were made with AG-S4. [62]

By the late 1940s, newer materials were superseding Bakelite in many areas. [38] Phenolics are less frequently used in general consumer products today due to their cost and complexity of production and their brittle nature. They still appear in some applications where their specific properties are required, such as small precision-shaped components, molded disc brake cylinders, saucepan handles, electrical plugs, switches and parts for electrical irons, [63] as well as in the area of inexpensive board and tabletop games produced in China, Hong Kong and India. [63] Items such as billiard balls, dominoes and pieces for board games such as chess, checkers, and backgammon are constructed of Bakelite for its look, durability, fine polish, weight, and sound. Common dice are sometimes made of Bakelite for weight and sound, but the majority are made of a thermoplastic polymer such as acrylonitrile butadiene styrene (ABS). Bakelite continues to be used for wire insulation, brake pads and related automotive components, and industrial electrical-related applications. Bakelite stock is still manufactured and produced in sheet, rod and tube form for industrial applications in the electronics, power generation and aerospace industries, and under a variety of commercial brand names. [38]

Phenolic resins have been commonly used in ablative heat shields. [64] Soviet heatshields for ICBM warheads and spacecraft reentry consisted of asbestos textolite, impregnated with Bakelite. [65] Bakelite is also used in the mounting of metal samples in metallography. [66]

Collectible status

Bakelite items, particularly jewelry and radios, have become a popular collectible. [38] The term Bakelite is sometimes used in the resale market to indicate various types of early plastics, including Catalin and Faturan, which may be brightly colored, as well as items made of Bakelite material. [37] [67]

Patents

The United States Patent and Trademark Office granted Baekeland a patent for a "Method of making insoluble products of phenol and formaldehyde" on December 7, 1909. [8] Producing hard, compact, insoluble and infusible condensation products of phenols and formaldehyde marked the beginning of the modern plastics industry. [68]

Similar plastics

See also

Related Research Articles

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Thermoplastic plastic that becomes soft when heated and hard when cooled

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Catalin is a brand name for a thermosetting polymer developed and trademarked in 1927 by the American Catalin Corporation of New York City, when the company acquired the patents for Bakelite. A phenol formaldehyde resin, it can be worked with files, grinders, and cutters, and polished to a fine sheen.

Leo Baekeland Belgian-American chemist

Leo Hendrik Baekeland FRSE(Hon) was a Belgian chemist. He is best known for the inventions of Velox photographic paper in 1893 and Bakelite in 1907. He has been called "The Father of the Plastics Industry" for his invention of Bakelite, an inexpensive, nonflammable and versatile plastic, which marked the beginning of the modern plastics industry.

Phenol formaldehyde resin chemical compound

Phenol formaldehyde resins (PF) or phenolic resins are synthetic polymers obtained by the reaction of phenol or substituted phenol with formaldehyde. Used as the basis for Bakelite, PFs were the first commercial synthetic resins (plastics). They have been widely used for the production of molded products including billiard balls, laboratory countertops, and as coatings and adhesives. They were at one time the primary material used for the production of circuit boards but have been largely replaced with epoxy resins and fiberglass cloth, as with fire-resistant FR-4 circuit board materials.

Formica (plastic) brand of composite materials

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Fibre-reinforced plastic (FRP) is a composite material made of a polymer matrix reinforced with fibres. The fibres are usually glass, carbon, aramid, or basalt. Rarely, other fibres such as paper, wood, or asbestos have been used. The polymer is usually an epoxy, vinyl ester, or polyester thermosetting plastic, though phenol formaldehyde resins are still in use.

Polyoxymethylene polymer

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Faturan

Faturan, in Middle Eastern beadwork, is a material used to make beads, notably in the making of komboloi and misbaha.

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Resin casting is a method of plastic casting where a mold is filled with a liquid synthetic resin, which then hardens. It is primarily used for small-scale production like industrial prototypes and dentistry. It can be done by amateur hobbyists with little initial investment, and is used in the production of collectible toys, models and figures, as well as small-scale jewellery production.

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