Nylon, a Petroleum Polymer

The world’s first synthetic fiber was the petroleum product “Nylon 6,” discovered in 1935 by a DuPont chemist who produced the polymer from chemicals found in oil.

DuPont Corporation foresaw the future of “strong as steel” artificial fibers. The chemical conglomerate had been founded in 1802 as a Wilmington, Delaware, manufacturer of gunpowder. The company would become a global giant after DuPont scientists created incredibly durable and versatile products, including nylon, rayon, and lucite.

petroleum product nylon

“Women show off their nylon pantyhose to a newspaper photographer, circa 1942,” noted historian Jennifer S. Li in “The Story of Nylon – From a Depressed Scientist to Essential Swimwear.” Photo by R. Dale Rooks (1917-1954).

The world’s first synthetic fiber — nylon — was discovered on February 28, 1935, by a former Harvard professor working at a DuPont research laboratory. Called Nylon 6 by scientists, the revolutionary carbon-based product came from chemicals found in petroleum.

Man-made fiber Nylon 6 illustration of its six carbon atoms per molecule.

Chemists called the man-made fiber Nylon 6 because chains of adipic acid and hexamethylene diamine each contained six carbon atoms per molecule.

Professor Wallace Carothers had experimented with artificial materials for more than six years. He previously discovered neoprene rubber (commonly used in wet suits) and made major contributions to understanding polymers — large molecules composed in long chains of repeating chemical structures.

Just 32 years old, Carothers created fibers when he combines the chemicals amine, hexamethylene diamine, and adipic acid. He formed a polymer chain using a process in which individual molecules join together with water as a byproduct.

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However, the fibers were weak, explains a PBS series, A Science Odyssey: People and Discoveries. “Carothers’ breakthrough came when he realized the water produced by the reaction was dropping back into the mixture and getting in the way of more polymers forming,” notes the PBS website. “He adjusted his equipment so that the water was distilled and removed from the system. It worked!”

DuPont named the petroleum product nylon — although chemists called it Nylon 6 because the adipic acid and hexamethylene diamine each contain six carbon atoms per molecule.

1938 ad for petroleum product nylon bristles on toothbrushes.

“Until now, all good toothbrushes were made with animal bristles,” noted a 1938 ad.

Each man-made molecule consists of 100 or more repeating units of carbon, hydrogen, and oxygen atoms, strung in a chain. A single filament of nylon may have a million or more molecules, each taking some of the strain when the filament is stretched.

There’s disagreement about how the product name originated at DuPont.

“As to the word nylon, it’s actually quite arbitrary. DuPont itself has stated that originally the name was intended to be No-Run (that’s run as in the sense of the compound chain of the substance unravelling), but at the time there was no real justification for the claim, so it needed to be changed,” noted Chris Nickson in a 2017 website post, Where Does the Name Nylon Originate?

Replacing Hog Bristles

The first commercial use of this revolutionary petroleum product was for toothbrushes.

On February 24, 1938, the Weco Products Company of Chicago, Illinois, began selling its new “Dr. West’s Miracle-Tuft” — the earliest toothbrush to use synthetic DuPont nylon bristles.

Petroleum product nylon used for women's stockings in a DuPont 1948 ad.

First used for toothbrush bristles, nylon women’s stockings were promoted in a DuPont 1948 ad.

Americans will soon brush their teeth with nylon — instead of hog bristles, declared an article in the New York Times. “Until now, all good toothbrushes were made with animal bristles,” proclaimed a 1938 Weco Products advertisement in Life magazine. “Today, Dr. West’s new Miracle-Tuft is a single exception. It is made with EXTON, a unique bristle-like filament developed by the great DuPont laboratories, and produced exclusively for Dr. West’s.”

Pricing its toothbrush at 50 cents, the Weco Products Company guaranteed “no bristle shedding.” Johnson & Johnson of New Brunswick, New Jersey, will introduce a competing nylon-bristle toothbrush in 1939.

Nylon Stockings

Although DuPont patented nylon in 1935, it was not officially announced to the public until October 27, 1938, in New York City. A DuPont vice president unveiled the synthetic fiber — not to a scientific society or industry association — but to 3,000 Women’s Club members gathered at the site of the upcoming 1939 New York World’s Fair.

During WWII, Nylon was used as a substitute for silk in parachutes.

During WWII, nylon was used as a substitute for silk in parachutes.

“He spoke in a session entitled ‘We Enter the World of Tomorrow,’ which was keyed to the theme of the forthcoming fair, the World of Tomorrow,” explained DuPont historian David A. Hounshell in a 1988 book.

The petroleum product was an instant hit, especially as a replacement for silk in hosiery. DuPont built a full-scale nylon plant in Seaford, Delaware, and began commercial production in late 1939. The company purposefully did not register “nylon” as a trademark – choosing to allow the word to enter the American vocabulary as a synonym for “stockings.”

Women’s nylon stockings appeared for the first time at Gimbels Department Store on May 15, 1940. World War II would remove the polymer hosiery to make nylon parachutes and other vital supplies.

Nylon would become far and away the biggest money-maker in the history of DuPont. The powerful material from lab research led company executives to derive formulas for growth, according to Hounshell in The Nylon Drama.

“By putting more money into fundamental research, Du Pont would discover and develop ‘new nylons,’ that is, new proprietary products sold to industrial customers and having the growth potential of nylon,” Hounshell explained in his 1988 book.

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Carothers did not live to see the widespread application of his work — in consumer goods such as toothbrushes, fishing lines, luggage and lingerie, or in special uses such as surgical thread, parachutes, or pipes — nor the powerful effect it had in launching a whole era of synthetics.

Devastated by the sudden death of his favorite sister in early 1937, Carothers committed suicide in April of that year. The DuPont Company would name its research facility after him.

As the DuPont website notes, the invention of nylon radically changed the way people dressed worldwide —  and rendered the term ‘silk stocking’ obsolete (and once an epithet directed at the wealthy elite). The financial success of Nylon encouraged DuPont to adopt long-term strategies for other new products developed from basic research.

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Recommended Reading: The Golden Thread: How Fabric Changed History (2019); Enough for One Lifetime: Wallace Carothers, Inventor of Nylon (2005); The Nylon Drama (1988). Your Amazon purchases benefit the American Oil & Gas Historical Society; as an Amazon Associate, AOGHS earns a commission from qualifying purchases.

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The American Oil & Gas Historical Society preserves U.S. petroleum history. Become an AOGHS annual supporting member and help maintain this energy education website and expand historical research. For more information, contact bawells@aoghs.org. © 2022 Bruce A. Wells. All rights reserved.

Citation Information – Article Title: “Nylon, a Petroleum Polymer.” Authors: B.A. Wells and K.L. Wells. Website Name: American Oil & Gas Historical Society. URL: https://aoghs.org/products/petroleum-product-nylon-fiber. Last Updated: February 21, 2022. Original Published Date: February 23, 2014.

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Wham-O and Petroleum Product Hoopla

Oil Company chemists invented a new plastic, but transition from lab to market proved difficult. Enter Wham-O.

 

In 1954, two research scientists at an Oklahoma-based oil and natural gas company invented a high-density polyethylene. The company’s marketing executives named the new petroleum product Marlex, but searched in vain for buyers of the plastic. Then the Wham-O toy company found the durable plastic ideal for making hoops and flying platters.

Prompted by a post World War II boom in demand for plastics, Phillips Petroleum Company invested $50 million to bring its own miracle product — Marlex — to market in 1954. With a high melting point and tensile strength, the synthetic polymer would stand out from among thousands of the company’s patents.

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Oleaginous History of Wax Lips

Petroleum paraffin soon found its way into candles, crayons, chewing gum…and a peculiar wax candy.

 

When Ralphie Parker and his 4th-grade classmates dejectedly handed over their Wax Fangs to Mrs. Shields in “A Christmas Story,” a generation might be reminded of what a penny used to buy at the local Woolworth’s store. But there is far more to these paraffin playthings than a penny’s worth of fun. 

It’s hard to recall a time when there were no Wax Lips, Wax Moustaches, or Wax Fangs for kids to smuggle into classrooms. Many grownups may remember the peculiar disintegrating flavor of Wax Lips from bygone Halloweens and birthday parties, but few know where these enduring icons of American culture actually started.

The answer can be found by way of the oil patch.

Beginning with the August 1859 first commercial U.S. oil well, Pennsylvania oilfields quickly brought an important new source of light and other petroleum products.

“This flood of American petroleum poured in upon us by millions of gallons, and giving light at a fifth of the cost of the cheapest candle,” wrote British chandler James Wilson in 1879.

Wax lips petroleum product featured in 1984's A Christmas story

The 1984 holiday classic “A Christmas Story” featured Ralphie, his 4th-grade classmates – and a popular petroleum product for kids. Photos courtesy MGM Home Entertainment.

As kerosene lanterns replaced candles for illumination, the much-reduced candle business turned from tallow to versatile paraffin.

A byproduct of kerosene distillation, paraffin found its way from refinery to marketplace in candles, sealing waxes and chewing gums. Ninety percent of all candles by 1900 used paraffin as the new century brought a host of novel uses. Thomas Edison’s popular new phonographs also needed paraffin for their wax cylinders.

Crayons were introduced by the Binney & Smith Company in 1903 and were instantly successful. Alice Binney came up with the name by combining the French word for chalk, craie, with an English adjective meaning oily, oleaginous: Crayola (see Carbon Black and Oilfield Crayons).

Wack-O-Wax lips petroleum product red candy lips.

Concord Confections, part of Tootsie-Roll Industries, continues to produce Wax Lips and other paraffin candies for new generations of schoolchildren.

In New York City, after collecting unrefined waxy samples from Pennsylvania oil wells, Robert Chesebrough invented a method for turning paraffin into a balm he called “petroleum jelly,” later “Vaseline.” His product also led to a modern cosmetic giant (learn more in The Crude History of Mabel’s Eyelashes).

Paraffin Lips, Fangs, and Horses Teeth

An inspired Buffalo, New York, confectioner soon used fully refined, food-grade paraffin and a sense of humor to find a niche in America’s imagination.

When John W. Glenn introduced children to paraffin “penny chewing gum novelties,” his business boomed. By 1923, his J.W. Glenn Company employed 100 people, including 18 traveling sales representatives. Glenn Confections became the wax candy division of Franklin Gurley’s nearby W.&F. Manufacturing Company. There, the ancestors of Wax Lips chattered profitably down the production line. Among the most popular of these novelties at the time were Wax Horse Teeth (said to taste like wintergreen).

By 1939, Gurley was producing a popular series of holiday candles for the Socony-Vacuum Oil Company using paraffin from a nearby refinery at Olean, New York – once home to the world’s largest crude oil storage site. A field of metal tanks, some holding 20,000 gallons of paraffin, stood next to Gurley’s W.&F. Manufacturing Company in Buffalo.

wax fangs chewing gum candy.

Glenn Confections, the candy division of W. & F. Manufacturing Company, produced Fun Gum Sugar Lips, Wax Fangs, and Nik-L-Nips.

Decorative and scented paraffin candles soon became the company’s principal products, accounting for 98 percent of W.&F. Manufacturing sales. Gurley’s “Tavern Candle” Santas, reindeer, elves and other colorful Christmas favorites today are prized by collectors on eBay, as are his elaborately molded Halloween candles.

As W.&F.’s wax candy division, Glenn Confections, has continued to manufacture Fun Gum Sugar Lips, Wax Fangs, and Nik-L-Nips.

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In Emlenton, Pennsylvania, a few miles south of Oil City, the Emlenton Refining Company (and later the Quaker State Oil Refining Company) provided the fully refined, food-grade paraffin for these bizarre but beloved treats.

Retired Quaker State employee Barney Lewis remembers selling Emlenton paraffin to W.&F. Manufacturing. During a 2005 interview he noted, “It was always fun going to the plant…they were very secret about how they did stuff, but you always got a sample to bring home,” adding, “Wax Lips, Nik-L-Nips…the little Coke bottle-shaped wax, filled with colored syrup.”

Today, Concord Confections, a small part of Tootsie-Roll Industries, continues to produce Wax Lips and other paraffin candies for new generations of schoolchildren. The modern petroleum industry produces an astonishing range of products for consumers. But among the many products that find their history in the oilfield, few are as unique and peculiar as Wax Lips.

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Recommended Reading: Sweet!: The Delicious Story of Candy (2009); How Sweet It Is (and Was): The History of Candy (2003). Your Amazon purchase benefits the American Oil & Gas Historical Society. As an Amazon Associate, AOGHS earns a commission from qualifying purchases.

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The American Oil & Gas Historical Society preserves U.S. petroleum history. Become an AOGHS annual supporting member and help maintain this energy education website and expand historical research. For more information, contact bawells@aoghs.org. Copyright © 2021 Bruce A. Wells. All rights reserved.

Citation Information – Article Title: “Oleaginous History of Wax Lips.” Authors: B.A. Wells and K.L. Wells. Website Name: American Oil & Gas Historical Society. URL: https://aoghs.org/products/an-oleaginous-history-of-wax-lips. Last Updated: December 18, 2021. Original Published Date: December 1, 2006.

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Ethyl Anti-Knock Gas

General Motors scientists discover anti-knock properties of tetraethyl lead gasoline in 1921.

 

By 1923, many American motorists would be driving into service stations nationwide and saying, “Fill ‘er up with Ethyl.” 

Early internal combustion engines often suffered from a severe “knocking,” the out-of-sequence detonation of the gasoline-air mixture in a cylinder. The constant shock added to exhaust valve wear and frequently damaged engines. In November 1900, gasoline-powered autos were the least popular (see Cantankerous Combustion – First U.S. Auto Show).

General Motors chemists Thomas Midgely Jr. and Charles F. Kettering.

General Motors chemists Thomas Midgely Jr. and Charles F. Kettering.

On December 9, 1921, after five years of lab work to find an additive to eliminate pre-ignition “knock” problems of gasoline, General Motors researchers Thomas Midgely Jr. and Charles Kettering discovered the anti-knock properties of tetraethyl lead. Their early experiments had examined the properties of knock suppressors such as bromine, iodine and tin — and compared these to new additives such as arsenic, sulfur, silicon and lead.

Gas pump with "Ethyl" logo for tetraethyl lead gasoline

Halth concerns resulted in the phase-out of tetraethyl lead beginning in 1976.

When the two GM chemists synthesized tetraethyl lead and tried it in their one-cylinder laboratory engine, the knocking abruptly disappeared. Fuel economy also improved. “Ethyl” vastly improved gasoline performance.

Although being diluted to a ratio of one part per thousand, the lead additive yielded gasoline without the loud, power-robbing knock. With other scientists watching, the first car tank filled with leaded gas took place on February 2, 1923, at the Refiners Oil Company service station in Dayton, Ohio.

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In the beginning, GM provided Refiners Oil Company and other service stations special equipment, simple bolt on adapters called “Ethylizers” to meter the proper proportion of the new additive.

“By the middle of this summer you will be able to purchase at approximately 30,000 filling stations in various parts of the country, a fluid that will double the efficiency of your automobile, eliminate the troublesome motor knock, and give you 100 percent greater mileage,” Popular Science Monthly reported in 1924.

Ohio service station sells Ethyl gas for the first time.

“Ethyl” gasoline goes on sale for the first time at this Dayton, Ohio, service station. In foreground pump, GM’s bolt on “Ethylizer” is visible, running vertically alongside the visible reservoir. Photo courtesy Kettering/GMI Alumni Foundation.

Anti-knock gasoline containing a tetraethyl lead compound also proved vital for aviation engines during World War II, even as danger from the lead content increasingly became apparent.

Powering Allied Victory in World War II 

Aviation fuel technology was still in its infancy in the 1930s. The properties of tetraethyl lead proved vital to the Allies during World War II. Advances in aviation fuel increased power and efficiency, resulting in the production of 100-octane aviation gasoline shortly before the war.

Phillips Petroleum – later ConocoPhillips – was involved early in aviation fuel research and had already provided high gravity gasoline for some of the first mail-carrying airplanes after World War I.

Phillips Petroleum WWII ad for tetraethyl lead aviation gasoline.

Phillips Petroleum produced tetraethyl leaded aviation fuels from high-quality oil found in Osage County, Oklahoma, oilfields.

Phillips Petroleum produced aviation fuels before it produced automotive fuels. The company’s gasoline came from the high-quality oil produced during the Osage County oil boom, which began in 1917.

Although today still an ingredient of 100 octane “avgas” for piston-engine aircraft, tetraethyl’s danger to public health was underestimated for decades.

Tetraethyl lead’s Deadly Side

Leaded gasoline was extremely dangerous from the beginning, according Deborah Blum, a Pulitzer-Prize winning science writer. “G.M. and Standard Oil had formed a joint company to manufacture leaded gasoline, the Ethyl Gasoline Corporation,” she noted in a January 2013 article. Research focused solely on improving the formula, not on the danger of the lead additive.

1932 magazine ad Eythl gas additive.

A 1932 magazine ad promoted wildly improved high-compression engine performance.

“The companies disliked and frankly avoided the lead issue,” Blum wrote in “Looney Gas and Lead Poisoning: A Short, Sad History” at Wire.com. “They’d deliberately left the word out of their new company name to avoid its negative image.”

In 1924, dozens were sickened and five employees of the Standard Oil Refinery in Bayway, New Jersey, died after they handled the new gasoline additive. By May 1925, the U.S. Surgeon General called a national tetraethyl lead conference, Blum reported, and an investigative task force was formed. Researchers concluded there was ”no reason to prohibit the sale of leaded gasoline” as long as workers were well protected during the manufacturing process.

So great was the additive’s potential to improve engine performance, the author notes, by 1926 the federal government approved continued production and sale of leaded gasoline. “It was some fifty years later – in 1986 – that the United States formally banned lead as a gasoline additive,” Blum added.

By the early 1950s, American geochemist Clair Patterson discovered the toxicity of tetraethyl lead; phase-out of its use in gasoline began in 1976 and was completed by 1986. In 1996, EPA Administrator Carol Browner declared, “The elimination of lead from gasoline is one of the great environmental achievements of all time.”

Learn more about high-octane fuel in Flight of the Woolaroc and and early engines in Cantankerous Combustion – First U.S. Auto Show.

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Recommended Reading: An Illustrated Guide to Gas Pumps (2008); Unleaded: How Changing Our Gasoline Changed Everything (2021). Your Amazon purchase benefits the American Oil & Gas Historical Society. As an Amazon Associate, AOGHS earns a commission from qualifying purchases.

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The American Oil & Gas Historical Society preserves U.S. petroleum history. Join AOGHS and help maintain this energy education website, expand historical research, and extend public outreach. For annual sponsorship information, contact bawells@aoghs.org. © 2021 Bruce A. Wells. All right reserved.

Citation Information – Article Title: “Ethyl Anti-Knock Gas.” Authors: B.A. Wells and K.L. Wells. Website Name: American Oil & Gas Historical Society. URL: https://aoghs.org/products/tetraethyl-lead-gasoline. Last Updated: December 5, 2021. Original Published Date: December 7, 2014.

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Making a Two-Wick Camphene Lamp

 

Prior to the Civil War, the most popular lamp fuel in the country was a “burning fluid” called camphene, a volatile combination of turpentine and alcohol with camphor oil added for aroma. Until replaced by kerosene and its much safer lamps, two-wicked camphene lamps provided a cheap, bright light.

The fuel camphene’s explosive nature required a double burner, according to Ron Miller, a self-taught tinsmith and “hands-on historian.” He became so fascinated by America’s early illuminating lamps that recreated them.

Reproduction camphene, kerosene, and whale oil lamps.

Jim Miller’s 19th century lamp tin recreations, left to right: a whale oil burner; an 1842 patented lard oil burner; a “Betty Lamp” fueled by fat; and a typical camphene two-wicked lamp.

“This adventure has deepened my appreciation for past craftsmanship and the intelligence of common place things in early America,” explained Miller in his 2012 For the love of History blog. “Besides, now I have all this cool stuff to play (teach) with.”

The key to learning about early to mid-19th century oil lamps was to study their burners, Miller noted (see Camphene to Kerosene Lamps), adding, “each type of fuel needed a specific style of burner to give the best light.”

Although most of the fuels have become obsolete, Miller “wanted to faithfully replicate the burners, in order to understand how they evolved,” he said, adding, “For the time being, substitute fuels would have to do.”

Miller fashioned tin into period lamp designs, including one fueled by fat — a “Betty Lamp” that “has an ancestry extending clear back to the Romans but had been improved on over time.” He also recreated a whale oil lamp, circa 1850, and a patented lard oil burner of 1842 (the lard needed to be warmed, to improve its fluidity).

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After completing his first three tin lamp reproductions, the amateur tinsmith tackled the two-wicked camphene lamp. According to Miller, lamps fueled by camphene needed the two tapered, tubed burners angled out from each other to dissipate heat of the flames.

“These tubes never extend down past the mounting plate and never have slots for wick adjustment. Apparently, any heat added to the fuel caused an accumulation of gases and the possibility of an explosion,” he noted. Most surviving original burners have little covers to snuff out the flame and keep the fuel from evaporating.

“The style of lamp I chose to replicate is sometimes called a petticoat lamp by collectors for the flared shape of the base. Camphene lamps are often mislabeled as Whale Oil lamps but the difference is obvious once you know your burners,” Miller concluded about his replica.

“In case you wondered, my lamp burns modern lamp oil as I don’t need to kill myself in the pursuit of history,” the tinsmith added.

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Recommended Reading:  Oil Lamps The Kerosene Era In North America (1978). Your Amazon purchase benefits the American Oil & Gas Historical Society. As an Amazon Associate, AOGHS earns a commission from qualifying purchases.

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The American Oil & Gas Historical Society preserves U.S. petroleum history. Become an AOGHS annual supporting member and help maintain this energy education website and expand historical research. For more information, contact bawells@aoghs.org. Copyright © 2022 Bruce A. Wells. All rights reserved.

Citation Information – Article Title: “Making a Two-Wick Camphene Lamp.” Authors: B.A. Wells and K.L. Wells. Website Name: American Oil & Gas Historical Society. URL: https://aoghs.org/products/two-wick-camphene-lamp. Last Updated: January 25, 2022. Original Published Date: March 11, 2018.

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Seeking Star Oil Company

Researching a Chicago oil products company sign.

 

A Chicago college student in January 2021 emailed the American Oil & Gas Historical Society seeking research advice about a recently found porcelain sign from the Star Oil Company. “I’ve tried to do some research on it but I haven’t even found a place to start,” he noted. (more…)

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