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A New Way To Stick

Start-up company Sirrus is advancing novel chemistry for adhesives and coatings

by Michael McCoy
June 30, 2014 | A version of this story appeared in Volume 92, Issue 26

Reaction scheme shows producing diethyl methylene malonate from diethyl malonate and formaldehyde.

Automakers and other industrial companies have only three high-strength adhesive chemistries to choose from when they want to cost-effectively bond critical parts together. A new company, Sirrus, claims to have developed a fourth.

Sirrus, a Cincinnati-area start-up, says it has found a way to manufacture 1,1-disubstituted alkene monomers at commercial scale for use in adhesives, sealants, coatings, and inks. It’s now working to convince automakers and paint companies that polymers based on the new chemicals offer more than the epoxies, urethanes, and acrylics they use today.

Sirrus was founded in 2009 as Bioformix by Bernard and Adam Malofsky, a father-and-son team of Ph.D. chemists. The elder Malofsky had spent 25 years with Loctite, now part of Henkel’s adhesives division.

Not having the money to pay for the research, the Malofskys compensated Shepherd with equity in their new firm. Today, Shepherd is a minority owner of Sirrus.

The Malofskys knew that disubstituted alkenes would make great bonding polymers, but they also knew that no one had been able to synthesize them on any appreciable scale. They had some ideas, so they engaged Shepherd Chemical, a family-owned firm in nearby Norwood, Ohio, to help develop a manufacturing process. They started with one of the most basic disubstituted alkenes, diethyl methylene malonate, or DMM.

Working with Shepherd during 2010 and 2011, Bioformix made about 5 kg of DMM, enough to get potential investors interested. The following year the Malofskys raised $13.6 million in venture capital in a funding round led by New York City-based Braemar Energy Ventures.

They also started building a staff. Jeffrey M. Sullivan left his job as chief technology officer at Shepherd to head R&D at Sirrus. And as head of corporate strategy the Malofskys brought in Jeff Uhrig, a chemical engineer who had led corporate development at Elevance Renewable Sciences, a biobased chemical company.

Credit: Sirrus
Sirrus chemists found a way to stabilize disubstituted alkene production.
Photo of a Sirrus scientist at work at the firm’s Loveland, Ohio, labs.
Credit: Sirrus
Sirrus chemists found a way to stabilize disubstituted alkene production.

Uhrig explains that he had helped bring Elevance to the cusp of commercial success and was looking for a new challenge. And he knew that Sirrus had a good story to tell potential investors and customers. “We have made something that no one else has been able to make before,” he says.

That something, DMM and other 1,1-disubstituted alkenes, is a family of monomers that Sirrus hopes will become a new staple of the adhesives and coatings industries. The company touts the monomers’ ability to cure through a base-activated anionic polymerization that avoids the solvents and ultraviolet light associated with many current materials. Sirrus also says it can reliably bond plastics, metals, glass, and wood with cure times ranging from instantaneous to 20 minutes.

But successfully manufacturing the monomers required several technological advances. For example, Sirrus scientists found stabilizers that prevent the degradation and spontaneous polymerization that had plagued synthesis in the past. They also developed a stabilizer package to prevent polymerization while in storage.

Technology in hand, the company has been transitioning from start-up to commercialization mode. Last December, Adam Malofsky stepped down as chief executive, and Uhrig took the reins. In April, Bioformix changed its name to Sirrus. It now employs 32 people. And to date, Uhrig says, the firm has raised about $30 million from Braemar and other investors.

With a chunk of that money, Sirrus did something that a lot of start-ups don’t do. It built a demonstration plant at its Loveland, Ohio, headquarters to produce DMM and other reactive monomers. Output is about 40 kg per week.

“It was a gutsy call for a start-up,” Uhrig says of the decision to build the facility. But although Sirrus has a patent on its process, it also depends on numerous trade secrets that he is loath to share with a contract manufacturer.

Sirrus is talking to potential users of its technology such as General Motors and the paint maker PPG Industries, according to Uhrig. Ideally, buy-in from a big customer would open the door to a commercial manufacturing partnership with a Dow Chemical or a BASF, he says. But Sirrus is raising more money, he adds, and is prepared to proceed alone.

Adhesives experts, meanwhile, are intrigued by Sirrus’s new adhesive molecules but a bit skeptical of the firm’s claims. For example, Jürgen Wegner, a former Henkel researcher now with the consulting firm ChemQuest, discounts Sirrus’s easy-cure claim, since many current industrial adhesives cure without solvents or ovens.

Paul A. Steiner, a former adhesives formulation chemist who now runs Steiner Consulting/The Adhesives Expert, notes that the most effective structural adhesives are highly aromatic compounds with high glass transition temperatures and good heat and UV resistance. He wonders whether polymers based on DMM, an aliphatic molecule, will hold up under stressful conditions.

Sullivan, Sirrus’s R&D head, responds that technicians from the major companies he has visited are quite keen about lowering solvent use in adhesives and coatings operations. And he notes that DMM is only one of many monomers that Sirrus can manufacture by swapping functional groups on the malonate backbone. Co­polymerizing different disubstituted alkenes offers another way to create new materials. “We have made dozens of analogs containing a wide range of functionality,” Sullivan says.

All involved in the field—including the Sirrus executivesagree that no one is going to use any of Sirrus’s products without testing them. In May, with the demonstration plant up and running, Uhrig traveled to Germany to meet with a company that wanted to try one of the company’s products. It was one of Sirrus’s first overseas shipments, and Uhrig was nervous when the container was opened.

The product had made the trip intact, however, and the German firm’s chemists started putting it through the motions. It bonded two sheets of glass almost instantly, Uhrig says. Then the chemists glued two pieces of polycarbonate together. They let the bond set, then put the joined plastic in clamps and started to pull. After much effort the plastic broke, but not at the bond. The adhesive based on a disubstituted alkene held.

The Germans were impressed, Uhrig recounts. “No one,” he says, “has seen this before.” 


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