KYMENE™ WET-STRENGTH RESIN INNOVATIONS Wet-strength Production Facilities

Solenis Facilities Because of our global reach, we are capable of providing wet-strength resins—efficiently and cost-effectively—to Licensee any mill, anywhere in the world.

Global Wet-strength Leader Solenis invented the modern era of wet-strength paper manufacturing with the introduction of Kymene™ 557 wet-strength resin, the first polyamido- amine-epichlorohydrin (PAE) resin ever brought to the market. The product was an instant commercial success, both as aminochlorohydrin (ACH) and polymer-bound CPD for its ability to function in neutral/alkaline papermaking (PB-CPD). Solenis has led the industry in decreasing processes and for its novel wet-strength capabilities. the organic chlorine content of its Kymene wet-strength Like all PAE resins, the polymer in Kymene 557H resins without compromising their efficiency. Our contains quaternary ammonium groups that adsorb onto scientists have developed manufacturing processes negatively charged paper fibers and that continue to with greater control to maximize the efficiency of how cross-link even as the paper dries and cures. That means epichlorohydrin is used to generate azetidinium chloride the wet strength of paper treated with Kymene wet-strength (AZE), the reactive portion of PAE resin, while minimizing resin continues to increase after it’s been put into storage. the levels of 1,3-DCP and 3-MCPD. We’ve also introduced Over the years, our researchers have modified the basic innovative technologies that can be applied after the chemistry to make stronger-performing resins with manufacture of the basic PAE resin to reduce harmful reduced by-products, 1,3-dichloropropanol (1,3-DCP) by-products. and 3-monochloropropan-1,2-diol (3-MCPD), as well Kymene™ Wet-strength Resin Portfolio

Today, PAE resins account for 90 percent of the wet-strength market. Of this market, nearly half bear the Kymene brand name. One reason for the success of the product is a broad range of configurations that enable papermakers to customize their wet-strength programs to satisfy regional demands and regulatory requirements. Solenis has introduced market-leading technologies into each of the widely used industry descriptors of G1, G1.5, G2, G2.5 and G3 PAE resins, making it possible to address a full range of customer compliance needs while balancing cost-in-use. Today, we offer the broadest portfolio in every region of the world and can provide solutions to satisfy even the most rigorous regulatory guidelines, including environmental labeling established by Nordic Ecolabel and recommendations issued by the German Federal Institute of Risk Assessment (Bundesinstitut für Risikobewertung, or BfR). Solenis’s wet-strength resins can be supplied in a wide range of solids content — from 13 percent total solids to 30 percent total solids — to help our customers balance freight costs, shelf life and product stability concerns.

Compliance Standards for Kymene Wet-strength Resins

We offer the broadest portfolio of BfR XXXVI /1/2/3 BfR XXXVI Non BfR wet-strength resins in the world, with

Non Total Chlorine Fr ee different product configurations to accommodate any mill’s compliance G1 standards, regardless of location. 1.00% G2 G1.5^ (wet basis) 1 Total Chlorine Free 0.10% G2.5 %A OX

G3

0.01% 0 1 10 100 1000 10000 1,3-DCP ppm (wet basis)

1 Adsorbable organic halogen ^ Only available in North America A History of Chemical Innovation

In the late 1950s, Solenis researchers began a quest to include 1,3-DCP and 3-MCPD, as well as ACH and find new wet-strength resins that could demonstrate PB-CPD. Both 3-MCPD and 1,3-DCP are considered good performance under neutral pH conditions. Their hazardous substances and are possible human efforts led to polyamido-amine-epichlorohydrin (PAE) carcinogens. And all of the chlorine-containing by- resin. Solenis filed its first patent application for PAE resin products, taken together, increase adsorbable organic technology in 1957, and just two years later, it began to halogen (AOX) levels in the effluent of paper mills. market Kymene™ 557 wet-strength resin effective at pH As a result, the use of PAE resins is highly regulated levels between 5 and 8. and allowable levels of by-products vary greatly from But our researchers didn’t just invent the PAE resin: country to country. Government regulators also provide They have continued to refine the chemistry to reduce stringent requirements for the use of wet-strength the by-products of the manufacturing process. In resins in food-packaging applications. Kymene wet-strength resin synthesis, those by-products

The Synthesis of Kymene O Epichlorohydrin H H O N N Cl Wet-strength Resins N O- H Although the basic reactions in the O Resin synthesis By-product formation synthesis of wet-strength resins are O well understood, we have introduced H H N N advanced process control and N O Cl C l Cl H O O OH OH purification techniques to increase 1,3-dichloropropanol (1,3-DCP) Aminochlorohydrin (ACH ) the efficiency of our products while Cl O - H C l H lowering their environmental impact. N + N H O Cl N O Cl OH O OH Polymer-bound CPD 3-monochloropropan-2-ol (3-MCPD) (PB-CPD) OH Azetidinium (Aze)

A History of Chemical Innovation

Kymene SLX wet-strength 1999 1957 resin—a G2 resin with less than 1,000 ppm 1,3-DCP—launches in Europe. First patent application filed for Another first is launched—the first G3 polyamido-amine-epichlorohydrin (PAE) resin allowing papermakers to manufacture resin technology, ushering in a new era with 1990 products with reduced or non-detectable Kymene 557 wet-strength resin. levels of 3-monochloropropan-1,2-diol (3-MCPD) and 1,3-DCP.

Kymene ULX wet-strength resin is introduced in Europe. 1980s This product takes advantage of “biodehalogenation” to become the first G3 wet-strength resin. Development begins on products containing less than 1,000 parts per million (ppm) of 1,3-dichloropropanol (1,3-DCP). 1993 Next-generation Resins

To help papermakers meet compliance standards and This led Solenis scientists to search for even better government regulations, Solenis further developed and purification techniques. In recent years, they have then incorporated ‘’biodehalogenation’’ into its wet- developed and perfected membrane separation strength resin manufacturing. This process relies on technology, which takes finished Kymene™ resin and naturally occurring microorganisms to convert 1,3-DCP passes it through a nanofiltration device, essentially and 3-MCPD to glycerol, a simple sugar alcohol that the removing all by-products. At the same time, membrane same microorganisms then use for food. Unlike other separation overcomes some of the limitations of the physiochemical methods used to reduce and remove biodehalogenation process related to solids and levels of epichlorohydrin residuals, biodehalogenation consumes functionality. As a result, Solenis has been able to produce very little energy, requires no additional chemicals and new high-solids, high-efficiency G2.5 and G3 resins with generates no additional waste stream. It does, however, even higher levels of azetidinium (AZE) functionality. limit the solids and level of functionality of the resins Papermakers who use our G3 resins produced with that can be purified this way, requiring papermakers to membrane separation technologies are able to maximize compromise on performance. wet-strength performance while decreasing levels of both 1,3-DCP and 3-MCPD and overall AOX.

Membrane Separation Technology

A decade of research has led to revolutionary membrane separation technology, which can help paper mills decrease levels of both 1,3-DCP and 3-MCPD and overall AOX.

Membrane separation technology is perfected, making it possible to G1.5, a low VOC high performing manufacture higher-solids, higher- 2012 resin, with excellent storage stability efficiency G3 wet-strength resins. launches in North America.

The G2.5 and G3 portfolio gets refreshed with the introduction 2008 of Kymene LHP and GHP 2017 wet-strength resins.

A completely new wet-strength resin EMEA portfolio refreshed with G2 and category—G2.5—is created when Kymene 2010 G2.3 products now containing <500 217LX wet-strength resin launches. ppm of 1,3-DCP.

The G1 portfolio gets updated to have 2005 much lower 1,3-DCP and 3-MCPD. 2015 2016 Wet Strength: Satisfying Consumer Demand

Solenis’ ongoing commitment to wet strength reflects an wet-strength platform and helped to clarify the increasing demand among consumers for paper products fundamental chemistry. Wet-strength resins are a class that remain strong even when wet. Today, any grade of of chemicals that adhere to pulp fibers and form linkages paper that needs to maintain its integrity after becoming between fibers through covalent bonding. These linkages wet relies on the application of a wet-strength agent. supplement and reinforce the natural hydrogen bonding These grades include tissue (facial, kitchen towel, wipers, in the dry sheet and, because they’re covalent, cannot be napkins and tableware), packaging (liquid packaging, broken by soaking in water and are resistant to cleaning aseptic container, carrier board, and other forms of food chemicals. Papers treated with these resins, such as kitchen packaging), and specialty (tea bag, coffee filter, labels, towels and wipers, typically have a wet breaking strength of currency, laminating grades, etc.). 30 percent or greater of their dry breaking strength. Solenis’ PAE resin inventions established the modern

Wet Strength by the Numbers

28% Towel/Wipers 16% Liquid Packaging Board 17% Facial Tissues  8% Carrier Board  6% Cup and Plate 24% Other Specialty Papers

Wet-strength papermaking is vitally important because of the prominence these grades have in day-to-day consumer activities and because governments carefully monitor any paper and board that comes into contact with food. Kymene™ Wet-strength Resin: Active Patents

G2.5 and G3: G3 via membrane separation:

US6554961 US7303652 US7932349

EP1189972 EP1337576 US8101710

EP1770109 CA2398630 EP2064265

AU755277 JP4266635 CA2663054

CA2375694 CN1293122 KR101387870

JP4666853 US7081512

US7175740 CA2526093

EP1337576 KR101168773

EP1770110

The Future of Wet Strength

As consumer needs and regulatory requirements All of these innovations will lead to a better Kymene continue to evolve, wet-strength chemistry must evolve product line that helps our customers adapt to changing with it, which is why the Kymene story is far from being industry requirements, deliver products that are both over. Solenis scientists continue to explore and refine functional and safe for consumers, increase sustainability the chemistry we invented at the same time that we and minimize associated environmental impacts. research commercially viable alternatives, with the goal of introducing next-generation wet-strength products that:

• Increase solids so significantly that paper mills can cut their deliveries by half, thereby significantly improving sustainability. • Improve functionality to significantly increase the wet- strength-to-dry-strength ratio papermakers can achieve. • Remain far ahead of all regulatory compliance issues by further reducing 1,3-DCP, 3-MCPD and total AOX. Solenis Strong Bonds. Trusted Solutions.

Solenis supplies specialty chemicals for water-intensive industries, including the pulp and paper, oil and gas, chemical processing, mining, biorefining and power markets. Whether you want to increase production, develop new products, reduce costs or simply do more with less, we can help. With our innovative technologies, passionate people and unrivaled experience, Solenis is ready to deliver the solutions you need.

To learn more, contact your technical sales representative or visit us online.

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