elements30 S c i e n c e N e w s l e t t e r 3 1 3 2 3 3 2 0 1 0

Evonik Innovation Award 2009 N e w Proce s s e s C a t e g o r y Nanofiltration Developed to Application Readiness

nPO e w R D U C T S C a t e g o r y New Functional Silanes for the Construction and Filler Industries

nS e w Y S T E M S O L U T i o n S C a t e g o r y CoverForm®: One-Step In-Mold Scratch Resistance for PMMA E D I torial

Using Resources Efficiently

Evonik will focus on its strengths in specialty chemicals. Our Executive Board‘s new business model, endorsed by the Supervisory Board, should make us one of the world‘s leading specialty chemicals companies. Energy will remain within the Group as a largely independently managed affiliate, and Evonik is seeking partners to finance growth projects in this area. Real Estate is being merged with THS GmbH to form a new company that in the medium term will be placed on the capital market as an independent player. The reason for the stronger focus on chemicals is that Evonik alone does not have the financial scope to develop all the three business areas equally and simultaneously. With the new business model, on the other hand, each business area can exploit its growth potential to the fullest. In Chemicals, the emphasis will be on technologies and products that use resources efficiently, contribute to the health and nutrition of the world‘s steadily growing population, and allow growth regions to press ahead with industrialization. Behind these major developments—resource efficiency, Patrik Wohlhauser health and nutrition, and globalization of technologies—stand attractive markets, in some of which Chairman of the Board Evonik has already attained leading global positions. We are, for instance, the world‘s largest supplier of Management of Evonik Degussa GmbH of chlorosilanes and an important producer of monosilanes, both key components for photovoltaic conversion of solar energy. And in the lithium-ion battery we have in our product portfolio one of the most promising options for the automotive electric drive. Nor do we lack for good ideas on how we can continue to support these major trends in the future. This issue presents three projects that have received our Innovation Award 2009. Our new functional silanes, for example, provide excellent corrosion protection for concrete, among other materials. They therefore allow the concrete cover on rebars to be thinner, thus saving concrete—a construction material whose production is well known to be highly energy intensive. Thanks to our research, nanofiltration is now also possible in organic solvents. Our developers have thus opened the door to more sustainable production in which, for example, solvents can be recovered by energy-saving nanofiltration rather than energy-intensive distillation. Finally, CoverForm®, a system solution devel­ oped jointly with KraussMaffei, produces, in a single step, injection-molded PLEXIGLAS® parts with surfaces that are highly scratch-proof and resistant to chemicals. This does away with the need for coating lines, shortens the value chain, and saves time and money. The market has dealt with all three developments very well because they are perfectly in tune with the current “megatrends” and allow efficient utilization of resources—not least because they are the result of a target-oriented innovation process that uses resources efficiently.

elements30 | 2010 e vonik I n n ovat i o n Awa r d 2 0 0 9 n ew s 4 The winner 23 New binder imparts high gloss and toughness to 6 New Processes category: plastic coatings Nanofiltration developed to application readiness 24 Thirty years of VESTOPLAST® contents 12 New Products category: 24 Evonik acquires Eli Lilly‘s U.S. tippecanoe New functional silanes for the construction and manufacturing site filler industries 25 Joint venture established for manufacture of glass lenses for LEDs n e w s 17 New highly flexible Polyamide 12 for cable conduits B I ot e c H N o lo g y 17 € 150 million invested in solar energy and electronics 26 Amino acids for specialty applications: markets of the future bright prospects for white biotechnology

e vonik I n n ovat i o n Awa r d 2 0 0 9 n e w s 18 New System Solutions category: 31 Evonik at Auto Expo India The cover photo shows CoverForm®: one-step in-mold scratch resistance 31 More than 300 VESTAMID® offshore lines in three years a test plant for organic for PMMA solvent nanofiltration 32 E v ent s a n d c r e d i t s

elements30 evonik science newsletter news

+++ Integrated production facility in Shanghai fully onstream

Evonik Industries has completed work on a large complex for base the Management Board of Evonik Degussa GmbH, highlighting and specialty methacrylates, polymethyl methacrylate (PMMA) the significance of this major project. The 25,000 square meter molding compounds and thermoplastic methacrylic resins, and has research center houses state-of-the-art laboratories for research, brought the 250-million-euro facility fully onstream after a con­ development, application, and technical service, and a pilot plant struction period of just two years. From the Shanghai site—the for polymer technology. Evonik employs about 300 people at the Shanghai Chemical Industry Park (SCIP), an area spanning sever- SCIP site in Shanghai. al square kilometers—the new facility supplies key intermediates Evonik now has integrated MMA production sites in the U.S., for such applications as eco-friendly coatings, concrete additives, Europe and China. „This allows our customers to procure prod­ and PMMA molding compounds for lightweight and therefore ucts from a single source in each of these regions,“ added Hetzke. fuel-saving plastic parts for vehicles. Methyl methacrylate (MMA) Moreover, Evonik can from now on offer much shorter delivery is a key product of the site. “The global market for MMA is grow­ times in Asia. “In this respect we‘re following our most important ing by 5 percent per year, and the growth rate in China is signifi­ global customers who are investing in China, and whom we can cantly higher even than that. It’s in this boom region that we’re now supply here with locally produced materials.” starting up our new facility. Thanks to our new integrated produc- Over the next few years, Evonik expects steady growth for tion facility, ours is the only company in the region that can offer methacrylates and PMMA molding compounds. Among the most nearly all specialty products in this category locally,” said Dr. Klaus important drivers here is the energy efficiency megatrend. W“ ith Engel, chairman of the Executive Board of Evonik Industries AG. our products we offer a number of solutions, such as for the solar industry and for weight reduction in the automotive industry. Our New C4 process expands the technology platform materials are also increasingly finding application in construction MMA is produced by the C4 process, a new process for Evonik. and architecture, and in noise control,” said Hetzke. For the sake of raw material flexibility, a plant for splitting TM BE, With its PLEXIGLAS® molding compounds, Evonik is also mak­ a widely-available basic petrochemical, has been built along with ing a key contribution to the booming electronics industry in the the MMA facility. The plant uses a new process that was devel­ new generation of LED flat screens.I n the area of paints and coat­ oped in Evonik’s C4 Chemistry Business Line, and is being used ings, the company has developed in its VISIOMER® monomers for the first time in Shanghai.T he process increases flexibility and important products for waterborne formulations that are environ- significantly improves the cost situation for MMA production at mentally friendly—an important future consideration in China. the site. “With this project we have implemen- ted a unique integrated production con- cept, and with the decision to build a C4 plant for MMA production, we have also considerably expanded our technology platform,” said Gregor­ Hetzke, head of Evonik’s Performance Polymers Business Unit. “With the integrated production facility and the research and development center in Shanghai,­ Evonik is turning into the larg­ est supplier of methacry­late specialties in China, said Patrik Wohlhauser, chairman of

Evonik’s new integrated production plant in Shanghai elements30 evonik science newsletter 3 Evonik Innovation Award 2009

Researchers at Inorganic Materials, Performance Polymers, Industrial Chemicals and Process Technology & Engineering have won the 2009 Innovation Award which Evonik Industries awards once each year to employees in the Chemicals Business Area for exceptional research performance.

Performance Polymers got top marks for CoverForm®, a system solution devel­ oped in collaboration with KraussMaffei which enables single-step processing of PLEXIGLAS® to molded components that boast exceptionally scratch-resist­ant and chemical-resistant surfaces.

An interdisciplinary team from Process Technology and Industrial Chemicals successfully employed a newly developed polymer in the first-ever application of organic solvent nanofiltration in a technical chemical process to recover an expensive rhodium-based homogeneous catalyst.

Inorganic Materials, for its part, was awarded the prize for its functional new silane systems which, among other merits, provide 35 years of protection against corrosion in cement while containing practically no volatile organic substances.

The three teams accepted their awards – including prize monies of 20,000 euro each – from Patrik Wohlhauser, Chairman of the Management Board of Evonik Degussa GmbH, in Essen on December 16. This year’s competi- tion for the coveted trophy drew submissions from a total of 22 teams. Six of them presented new products, ten of them new or improved processes, and six others new system solutions. The jury, comprising in-house and external experts, assessed the projects based on defined criteria. For one thing, the entries had to re­­ present new developments which were either market mature or already launched on the market. They also had to offer eco- nomic as well as ecological benefits, and they were required to possess evident value for society. Marks were additionally given for originality and creativity.

4 elements30 evonik science newsletter Category Category Category New Processes New Products New System Solutions

Nanofiltration developed New functional silanes for the CoverForm®: one-step in-mold to application readiness construction and filler industries scratch resistance for PMMA

Stefan Drees Dr. Christine Fliedner Dr. Klaus Albrecht Dr. Robert Franke Dr. Manuel Friedel Rudolf Blass Dr. Hans-Gerd Lueken Dr. Sabine Giessler-Blank Arne Schmidt Patrick Muhlack Dr. Heidi Grön Sven Schröbel Dr. Markus Rudek Spomenko Ljesic Dr. Dominic Störkle Hermann-Josef Schulte-Althoff Reiner Störger Christian Eberle Dr. Klaus-Diether Wiese Dr. Kerstin Weißenbach Dr. Thorsten Goldacker Industrial Chemicals Business Unit Inorganic Materials Business Unit Klaus Koralewski Werner Höß Dr. Goetz Baumgarten Performance Polymers Christian Lingner Business Unit Markus Priske Process Technology & Engineering Service Unit

elements30 evonik science newsletter 5 N e w Proce s s e s C a t e g o r y

Nanofiltration Developed to Application Readiness

6 elements30 evonik science newsletter E v onik I n n o v a t i o n A w a r d 2 0 0 9

Nanofiltration Developed to Application Readiness

With the aid of a newly developed polymer, an interdisciplinary team consisting of members from Process Technology and Industrial Chemicals—two of Evonik’s units—has succeeded in using organic solvent nanofiltration for the first time in a technical process for recovering a costly homogeneous catalyst. For this notable technical and commercial breakthrough, the team has received the Innovation Award 2009 in the New Processes category.

atalytic processes are of paramount importance in The result is product contamination and high costs aris­ the chemical industry; more than 90 percent of all ing from catalyst losses: Homogeneous catalysts often con- chemical products undergo a catalytic process in at tain metals from the platinum group of the periodic table, least one stage of production. The reasons are including precious metals such as rhodium, palladium, and Cmany and various: Catalysts reduce energy consumption, platinum itself, which significantly raises costs, particularly save resources, and minimize costs, particularly if they can when raw materials prices are high. The specific ligands be recovered and reused. Homogeneous catalysis offers spe- required, which have a major influence on selectivity, are cial advantages. In this case, the catalyst and starting mate-­ usually also prohibitively expensive. rials­ are in the same phase, and the active centers of the According to experts' estimates, separation accounts for catalyst are therefore fully available for catalysis. For this 40 to 70 percent of production costs when homogeneous reason, homogeneous catalysts are often more active and catalysis is used. Given these costs, chemists continue to selective than heterogeneous catalysts. The high selectivity, search for extremely gentle alternatives to the distillation apart from their commercial advantages,­ contributes to pro- that is currently widely used. One promising approach here tecting the environment. is organic solvent nanofiltration. These properties make homogeneous catalysis of great interest to the chemical industry. In practice, however, chem­ Nanofiltration already in commercial ists often resort to heterogeneous catalysts, for the follow­ use for water treatment ing two reas­ons. Homogeneous catalysts are often in the form of metal complexes, with a central transition metal ion Nanofiltration is an established membrane process in water and ligands through which the catalytic properties can be treatment for removal of multivalent ions. In its rejection regulated.­ The catalyst is susceptible to poisoning, and in characteristics, it ranks between reverse osmosis and ultra- practice­ significant catalyst deactivation may therefore oc- filtration. Processes of this type are already being used for cur during the reaction. water softening and in the process industry for desalination Separating the homogeneous catalyst from the reaction of dyes and lactose recovery. Membranes suitable for water- mixture presents a considerably more difficult problem. The borne systems cannot be used in organic solvents, however. products formed must usually be separated from the catalyst The only commercial system for organic solvent nanofiltra- under conditions that do not damage the sensitive catalyst tion so far implemented is the MAX-DEWAX process used systems. This means that homogeneous catalysts can be re- in Exxon Mobil's Beaumont, Texas, refinery since 2001. This covered from the reaction mixture only with difficulty. recovers hexane, which is used to dewax lube oil, from lube oil/solvent mixtures at low temperatures. In certain important organic syntheses, organic solvent nanofiltration offers a new option for gently separating the homogeneous catalyst systems. The reactions concerned in- clude Suzuki coupling, a palladium catalyzed cross-coupling Evonik‘s test plant at the Marl between organoboronic acids and aryl halides; metathesis, Chemical Park for recovery of homogeneous catalysts by in which substituents at double or triple bonds are formally organic solvent nanofiltration exchanged in the presence of catalytically active >>>

elements30 evonik science newsletter 7 transition metal compounds; and hydroformylation. This Membrantechnik GmbH in Rheinfelden, the Technical last reaction is a reaction of olefins with a mixture of hydro- University of Darmstadt, and the University of Rostock. gen and carbon monoxide, known as syngas, to form alde- As one of the model processes, the developers used a hy- hydes. This synthetic pathway, discovered in 1938 by the droformylation reaction catalyzed by a rhodium complex German chemist Otto Roelen, is now one of the most im­ (fig. 1). In this process, thermal separation of the longer- portant­ homogeneously catalyzed reactions, the catalysts in chain aldehydes is a problem for the sensitive catalyst sys- this case being rhodium complexes. Aldehydes are in de- tem, which contains carbon monoxide in addition to ligands. mand as versatile intermediates in the production of various The products must be removed under high vacuum, so that families of compounds. These include principally alcohols the partial pressure of carbon monoxide approaches zero. and diols as well as carboxylic acids, esters, and amines, As a result, carbonyl groups are released from the rhodium which are also of great industrial importance. complex, leaving vacant coordination positions that are oc- cupied by other rhodium atoms. This leads to progressive Wanted: membrane materials that clustering that deactivates the catalyst. are stable in organic solvents The goal of the BMBF-funded project was therefore to investigate whether and how organic solvent nanofiltration The reason that nanofiltration has not been used so far in could be used as an alternative and to make this option com- production processes of this kind is that most membranes mercially useful. This would allow the separation to be car- are not stable in organic solvents and cannot achieve the re- ried out at significantly lower temperatures so that catalyst quired separation efficiency. Since they do, however, offer activity could be retained. enormous potential in chemical synthesis—for energy-effi­ The BMBF-funded project succeeded in showing that or- cient solvent recovery as well as in the recovery of homoge- ganic solvent nanofiltration is suitable for separating sensi- neous catalysts—a project funded by the BMBF (the German tive homogeneous catalysts of complex structure even from Federal Ministry of Education and Research) studied organic high-boiling components. Separation is thus achieved with­ solvent nanofiltration until mid-2009. out deactivation of the catalyst complex by progressive clus­- Jointly with external partners, researchers from Evonik's t­ering, and losses through catalyst decomposition are avoid­ Industrial Chemicals Business Unit and Process Technology ed. The project participants have also demonstrated that the & Engineering Service Unit have brought the nanofiltration process can be transferred from the bench scale tube to a process to readiness for industrial application. The partici- test reactor system. pants in this successful project, which ran for four years, As a basis for further development at Evonik, membrane were the GKSS Research Center in Geesthacht, GMT systems already available on the market have been screened.

+ Figure 1 H H O

Catalyst R O CO H R + + 2 + Ligand H

H

Aldehyde linear branched erwünscht unerwünscht

Vaporizer

Evonik uses homogeneously catalyzed hydroform­ ylation as one of the model processes for organic solvent nanofiltration. The thermal separation of

Reactor high-boiling solvents is a fundamental challenge

H2, CO here because the sensitive catalyst system can be deactivated in the process Catalyst High boiler ejection recirculation and catalyst losses

Olefin

8 elements30 evonik science newsletter E v onik I n n o v a t i o n A w a r d 2 0 0 9

Laboratory system for organic solvent nano- filtration (left). At the core of the system is the membrane module (middle photo). The photo on the right shows that the system works: After organic solvent nanofiltration the reaction solution has become colorless

Polyimides (PI) and silicones have been found to be rather cause it is highly stable in most organic solvents. Additionally, suitable as membrane materials. Appropriate systems using the GKSS Research Center modified the membrane to further these materials are offered by various producers in Germany, improve its properties. the U.K., and the Netherlands. The membranes are usually For the nanofiltration after the reactor, the following constructed in three sections consisting of a nonwoven base, pre­conditions must be fulfilled. An active catalyst complex a porous supporting layer, and the actual functional nanofil- has to be present for separation of the rhodium. The mem­ tration membrane (fig. 2). brane rejects the catalyst complex to the maximum possible After the available membranes were tested, a silicone- extent while the solvent passes through unhindered. The based membrane was found to offer the best solution be- membrane has to prove stable in olefins, paraffins, >>>

Figure 2 Preliminary tests showed that a silicone-based Day 1 Day 10 Day 100 membrane is best suited for organic solvent nano- filtration: It is permeable to high boilers and can in Rejection [%] principle reject the catalyst. However, the memb- rane swells in the course of time, thus becoming 100 increasingly permeable to the catalyst. The dia- gram shows how the rejection of the membrane 90% Rejection shifts in the direction of higher molecular weight as the swelling increases, an effect that is undesir­ able. The developers solved this problem by mo- difying­ the membrane material so that it can no longer swell 50

Below: SEM micrograph of a silicone-based organic solvent nanofiltration membrane Swelling

Molecular weight (high boilers)

Source: GKSS Research Center, Geesthacht

elements30 evonik science newsletter 9 Evonik has proven— initially in a laboratory setup and later in a test plant—that organic solvent nano- filtration works, and not just on the labor­a­ tory scale

Figure 3 Catalyst rejection [%] The catalyst rejection method investigated in the 100 test plant has proven to be technically feasible. Since 2006, the membrane material has been 90 optimized by modification so that catalyst rejection has now increased to more than 99 percent. 80 The photo on the right shows a membrane module for organic solvent nanofiltration 70 60

Aldehyde 50

40

30 Vaporizer 20

10

Reactor 0

H2, CO 2006 2008 2009 Membrane module High boiler Catalyst ejection and recirculation Organic solvent minimal nanofiltration catalyst losses

Olefin

10 elements30 evonik science newsletter E v onik I n n o v a t i o n A w a r d 2 0 0 9

alde­hydes, and alcohols. Furthermore, its temperature stab­ to introduce a completely new class of polymers in membrane ility must be as high as possible because the reaction compo- applications that allows organic solvents to be separated nents are extremely viscous at low temperatures and mass rather efficiently (fig. 4). The special feature of the new po- transfer would then be very slow. lymers is a structure that gives them intrinsic microporosi- In the test plant for organic solvent nanofiltration, the fil- ty, which results in extraordinarily high membrane perfor- trate, consisting mainly of the reaction product, was removed mance in con­junction with especially efficient separation, as from the system. The rhodium-ligand complex was rejected is required in advanced recovery processes. by the membrane and then concentrated. Along with fresh With this pioneering development, the researchers have starting material, the catalyst concentrate was then fed back paved the way for a more effective separation technology in into the reactor. Analysis of the kinetic data shows that the process industry allowing, for example, solvent recov­ membrane separation has no negative impact on catalyst ery by energy conserving nanofiltration instead of energy- activity. It has also been proven that rhodium rejection intensive distillation. l in­creases with increasing quantities of permeate because the membrane is partially reversibly compacted, which fur­ther improves separation efficiency. Contact Rhodium recovered virtually quantitatively Dr. Robert Franke Industrial Chemicals Business Unit R&D Manager The most important finding is the technical feasibility of the +49 2365 49-2899 process. The catalyst remains not only stable but also active [email protected] under the selected conditions. As a result, the valuable rho­ Dr. Markus Rudek d­ium can be recovered virtually quantitatively, thanks to na­ Industrial Chemicals Business Unit Plant Manager no­filtration, and used in the following reaction cycle (fig. 3). +49 2365 49-5823 Evonik has found that nanofiltration is a robust and stable [email protected] process, as was definitively proven by the successful opera- Dr. Goetz Baumgarten tion of the test plant. The company will therefore use this Senior Manager, Membrane Processes method as a platform technology, primarily for further de­ Process Technology & Engineering veloping homogeneous catalysis with its special advantages. Service Unit The team, which has now been awarded the Innovation +49 2365 49-2775 [email protected] Award, has built on the findings of the BMBF-funded project

Figure 4 On the basis of the results of the BMBF- funded project, a com- pletely new class of polymers possessing intrinsic microporosity has been developed for membrane applica- tions in conjunction with Evonik

elements30 evonik science newsletter 11 nPO e w R D U C T S C a t e g o r y

N ew Functional Silanes for the Construction and Filler Industries

Functional silanes open up new applications and improve existing ones in the construction and filler industries. As a starting point for their production, Evonik uses a side-stream from the synthesis of organofunctional silanes.

t the boundary between Berlin‘s Charlottenburg and Tiergarten districts stands the Charlottenburg Gate, an ornate neo-baroque structure dating from the early twentieth century. Situated between Ernst- AReuter-Platz and the Siegessäule on the Strasse des 17. Juni, it forms a counterpart to the Brandenburg Gate on the op­ posite side of the Tiergarten. Following the extensive resto­ ration­ of the actual structure last year, the Berlin restora- tion firm Opus is now taking in hand the two 22 meter high The Charlottenburg Gate in Berlin. candelabra that stood on the Charlottenburg side of the gate Protectosil® 851 was used in before they were destroyed in the Second World War. Be­ the restoration of the gate and fore the year ends, the two columns will be restored to their candelabra (not shown in the picture.) The water-repellent previous splendor. Originally of tufa, the candelabra will be concrete additive was the only reconstructed by Opus using a concrete mix that allows rep­ product that could meet the lication of the ocher color of the stone. And the concrete rigorous requirements on reduc- tion of water absorption, the also concea­ ls other surprises: An oligomeric alkylsilane that processability of the resulting Evonik has developed for the construction industry will, by its mixture, and the visual appearance water-repellent action, ensure the durability of the restored of the finished concrete candelabra. Employees of the integrated silicon production facility in the Inorganic Materials Business Unit have succeeded in developing oligomeric alkylsilanes from a side stream in the synthesis of organofunctional chlorosilanes to the extent that they open up entirely new possibilities for the construc- tion and filler industries. For this achievement the team has now received Evonik‘s Innovation Award for 2009 in the New Products category. The Inorganic Materials Business Unit is a globally active supplier of functional silanes, with a total of four production sites in the Europe, North America, and Asia Regions. The business unit works in close conjunction with strategic cus- tomers and develops together with them optimized silanes that help open up new market opportunities. Evonik pools product know-how in its Protectosil® and Dynasylan® functional silanes. Protectosil® offers solutions for water repellents, protection against graffiti and corrosion, and surface protection for a variety of materials including con­ crete, sandstone, granite, and stucco. The Dyna­sy­lan® >>>

12 elements30 evonik science newsletter E v onik I n n o v a t i o n A w a r d 2 0 0 9

New Functional Silanes for the Construction and Filler Industries

elements30 evonik science newsletter 13 brand, on the other hand, has for more than 50 years stood for silanes that help improve product properties in a widely Figure 1 Effect of Dynasylan® 9896 for waterproofing of fillers as observed in diverse range of industries, from paints and coatings through the model system of titanium dioxide in paraffin oil, compared with sealants and fillers to pharmaceuticals. untreated titanium dioxide and titanium dioxide treated with silicone or octylsilane. The filler treated with Dynasylan® 9896 is distinguished by very low viscosity and excellent dispersibility. This allows high filler Wanted: water-repellent building materials content and the finished structure, such as a window frame, has a that are easily processed smooth surface Titanium dioxide untreated treated: 0.2% silicone The construction industry needs high-performance chemi- treated: 1% octylsilane treated: 1% Dynasylan® 9896 cals that are easy to process at construction sites. For a wide Viscosity (Brookfield viscometer) [mPas] variety of substrates, water repellent action is the most 100,000 important requirement because this is the only way of pre- venting corrosion in reinforced concrete, alkali-silica reac- tions, or sulfate attack. 10,000 Corrosion of rebars is one of the major causes today for failure of concrete structures. A tragic example from the U.S. is the bridge carrying the Interstate 35 Highway in Minnesota, which collapsed on August 1, 2007. The filler in- 1,000 dustry also needs water repellents as cost-effective but high performance dispersants that should have a very low con- tent of volatile organic compounds. These are used primari- 100 ly for manufacturing window frames and plastic films. The oligomeric alkylsilane that Evonik obtains from a synthesis of organofunctional chlorosilanes is the base prod­ uct for the new development, which allows new and im­ 10 proved applications in the construction and filler industries. 1 10 100 The employees of the business unit have produced three Spindle speed [rpm] grades, which have different physical properties; there is also one customizable grade. Figure 2 Protectosil® DRY CIT bonds covalently to concrete, Low volatile organic compound content ensuring long-term corrosion protection

The products are Dynasylan® 9896 and Protectosil® 266. Dynasylan® 9896, aimed at the filler industry (fig. 1), has a significantly lower volatile organic compound content than the monomeric silanes that are frequently used as disper- Protectosil® protection sants. This is important for processing and also, from a broader­ viewpoint, because of increasing public concern in both Europe and the U.S. about hazardous gas emissions from organic compounds, with intense political debate on Substrate, e.g. concrete appro­priate limits. Dynasylan® 9896 has a high boiling point and is thus suitable even for applications where high safety require­ments must be met. The surface of a treated filler can be mod­ified even at relatively high temperatures without affect­ing the water-repellent action. 35 years of corrosion protection for concrete Protectosil® 266 on the other hand is an oligomeric alkyl- silane serving as an impregnating agent for absorbent min­ As early as 2008, Evonik received an award for Protectosil® eral facade construction materials. It is competitive with the DRY CIT at Deubau, Germany‘s most important trade show silicone-based products that have so far dominated this mar- for the construction industry. The organic sheath of the ket segment. powder system dissolves in the cement mix, releasing the As an aqueous emulsion, the product has the names active components where they are needed. The components Protectosil® WS 610 and WS 630, and as a powder Protectosil® bind covalently to the concrete in a chemical reaction, which DRY CIT. All the three are virtually free of volatile organic explains the remarkable durability of the corrosion protec- compounds. They allow the concrete cover of rebars to be tion (fig. 2). Tests confirm that Protectosil® DRY CITre- thinner; this reduces the required quantity of concrete, a mains effective for at least 35 years (fig. 3,4). In contrast, the construction material whose production is known to be corrosion control formulations available on the market are highly energy intensive. often good for only a few years. >>>

14 elements30 evonik science newsletter E v onik I n n o v a t i o n A w a r d 2 0 0 9

Figure 3 Unprotected concrete Electrodes Sensors Cl – 10mm depth 30mm depth 50mm depth

Current [µA] 20

50 mm 15

30 mm 10

10 mm 5

0 Corrosion measurement in untreated concrete and 0 100 200 300 400 500 600 in concrete treated with Protectosil® DRY CIT. Numbers of ponding days Sensors were inserted in a concrete block of edge length 15 cm, at depths of 10, 30, and 50 mm Concrete protected with 4 wt.% (relative to concrete weight) (figure above) of Protectosil® DRY CIT

The sensors were connected through an external 10mm depth 30mm depth 50mm depth resistance to a counter electrode, allowing Current [µA] measurement of corrosion current and the elec­ 20 trical resistance of the concrete. In each case, the concrete block was immersed for two days in a unimolar NaCl solution and then dried for five 15 days; the entire test extended over 520 days

In the unprotected concrete the sensors corrode 10 after a short time as is seen from the development of corrosion current, even when the concrete 5 cover is thick (figure above right)

By contrast, concrete protected with Protectosil® 0 DRY CIT shows no signs of corrosion over the 100 200 300 400 500 600 entire period (figure middle right). The duration of Numbers of ponding days the tests corresponds to corrosion protection for at least 35 years of outdoor exposure Water- Chloride content Resistance[kOhm] The results are collected in the table uptake [weight percent relative [g] to concrete weight]

Depth 0-15mm 15-30mm 10mm 30mm 50mm

Untreated concrete 39.3 6.25 5.78 0.417 0.312 0.288

Concrete treated with 13.5 3.28 2.22 2.3 14 99 2 weight percent (66% (48% (62% Protectosil® DRY CIT reduction) reduction) reduction)

Concrete treated with 11.6 1.55 0.46 128 185 275 4 weight percent (70% (75% (92% Protectosil® DRY CIT reduction) reduction) reduction)

Figure 4 Concrete without Protectosil® DRY CIT Important properties of fresh concrete such as flowability with 2 weight percent Protectosil® DRY CIT (relative to concrete weight) and bulk density remain unchanged upon addition of with 3 weight percent Protectosil® DRY CIT (relative to concrete weight) Protectosil® DRY CIT. Only the compressive strength of fresh samples shows a slight reduction, which, however, Compressive strength disappears as the hydration reaction progresses. After [N/mm2] 90 days the differences are usually barely measurable 60 50 40 30 20 10 0 0 20 40 60 80 100 Curing time [d]

elements30 evonik science newsletter 15 The Buda Castle in Budapest (Hungary) was restored in 2008. Since then, Protectosil® WS 630 has been protecting the walls against moisture

The fourth grade of the oligomeric alkylsilane is a custom­ izable solution: Protectosil® 60 SK can be rapidly adapted for Figure 5 The water-beading new customer requirements, for example, by the use of sui- effect of Protectosil® table catalysts, so that the water-repellent action of the pro- 60 SK remains duct can be fully developed even on substrates of lower al- intact even after 470 hours of artificial kalinity (fig. 5). weathering Ever since the market launch of the oligomeric alkylsi- lanes, the products have enjoyed increasing popularity

among customers, thanks to their excellent property profile. unweathered weathered In none of the grades could the oligomeric alkylsilane be used directly after its generation as a by-product in the syn- thesis of organofunctional chlorosilanes; various refining By contrast, the steps and extensive tests were necessary. With the powder effectiveness of a grade, for example, a problem arose on mixing the product commercially available water with concrete, when large quantities of air were introduced; repellent decreases the project team had to find a suitable defoamer that could significantly over be added to the powder. the same period Silane systems have long been used for their water repel- unweathered weathered lent action. They also have excellent corrosion inhibiting properties. Until now, however, they have always had the disadvantage of a high volatile organic substance content due to the alkoxy groups of the silanes. With their oligomer­ Contact ized alkylsilanes, the project team has succeeded in reduc­ing these unwanted emissions by up to 85 percent, making an Dr. Manuel Friedel l Applied Technology Silanes important contribution toward a healthier environment. for Building Protection Inorganic Materials Business Unit +49 7623 91-8206 [email protected]

16 elements30 evonik science newsletter news

+++ VerbundanlageNew highly flexible in Schanghai Polyamide komplett 12 for cablein Betrieb conduits genommen

Evonik Industries has extended its product range of flame-retardant polyamide 12 compounds for cable conduits and cable protection hoses. With VESTAMID® EX9203 black, a highly flexible molding compound, the company is responding to increasingly tough require­ ments in the electrical and cable industries and is supplementing its extensive portfolio of halogen-free flame-retardant plastics. VESTAMID® EX9203, which is colored black, is distinguished by excellent fire-retardant properties and a high oxygen index. With an elastic modulus of 770 MPa, it is highly flexible.T his outstandingly flexible and the highly impact-resistant material keeps on working even at temperatures as cold as –50°C. Halogen-free flame-retardant cable conduits and cable protection hoses are in demand, partic­ ularly for dynamically highly stressed components, as in rail vehicles, industrial plants, and mechanical engineering.

+++ € 150 million invested in solar energy and electronics markets of the future

In November 2009, Evonik Industries and its partner Taiyo Nip­ climate protection trends are important growth drivers for our pon Sanso Corporation (TNSC) in Yokkaichi (Japan) laid the cor­ business,“ said Engel. He added that with its commitment in nerstone­ for a future-oriented project to use environmentally Yokkaichi, the Evonik Group is taking the opportunity in this friendly solar energy. A traditional Shinto ceremony consecrated rapidly developing­ market to make a substantial contribution to the ground for the beginning of construction on an integrated climate protection through its innovative products and services. production plant for monosilane and AEROSIL®, the centerpiece Evonik has now signed a long-term supply agreement for mo- of the project, for which a total volume of € 150 million (¥20 bil- nosilane with TNSC, one of the foremost global distributors for lion) has been earmarked. Commissioning is scheduled for 2011. industrial and specialty gases, which includes silanes, and supplier TNSC and Evonik signed the agreement to implement the project to major customers in the electronics industry in Asia for many in May of this year, despite the worldwide economic crisis. “By years. Silanes are key components in the manufacture of ultra-pure beginning construction on time Evonik is pressing ahead with this silicon, an important raw material in the solar and electronics in- significant investment in solar energy and electronics, both mar- dustry. The silicon tetrachloride generated during monosilane kets of the future, and is taking a further step in the attractive production in Yokkaichi is processed into AEROSIL® and marketed

Ulrich Sieler, President Evonik Degussa Japan, at the Shinto ceremony. Electronic-quality mono- silane is needed for the manufacture of flat screens, among other applications

Asian market,“ says Dr. Klaus Engel, chairman of the Executive separately for applications in plastics, paints, and coatings, for ex- Board of Evonik Industries AG. ample, as well as adhesives and sealants. Evonik is already one of the worldwide leading producer of Evonik developed the monosilane production process itself chlorosilanes and a major producer of monosilane—both key and is already running a plant in Rheinfelden (Germany). The components for opening up the solar energy market. There is no Yokkai­ chi­ plant allows the company to produce electronics-grade end in sight for the worldwide solar boom. Based on forecasts, the monosilane for applications in thin-film photovoltaics, flat screens, world market for monosilanes alone is set to grow an annual 20 and semiconductors electronics, which are strong growth areas, percent, on average, by 2020. „The big energy efficiency and especially in Asia. elements30 evonik science newsletter 17 nS e w Y S T E M S O L U T i o n S C a t e g o r y

CoverForm®: One-Step In-Mold Scratch Resistance for PMMA

In an unusual collaboration, Evonik Industries and machine manufacturer KraussMaffei have set a milestone in plastics processing. Their jointly developed, single-step CoverForm® system solution produces injection-molded PLEXIGLAS® parts with highly scratch- and chemical- resist­ant surfaces, dramatically lowering production costs. For this achievement the developers of the process have now received the Evonik Innovation Award in the New System Solutions category. Experts in the trade are no less amazed: At the Materialica trade show in October 2009, CoverForm® won both the Materialica Design & Technology Award and the “Best of” award in the Surface & Technology category. In Darmstadt (Germany) Evonik established a Competence Center exclusively for the technology; since November 2009, customers and others have been getting a closer view of the technology and performing trial runs of their own samples.

Figure 1 Comparison of conventional Injection molding process process, consisting of injection Inspection Injection QA- molding followed by coating Transport upon delivery molding inspection of the part in a coating line (above), and the CoverForm® Coating process process. The latter reduces the number of process steps Cleaning Applying Primer Apply Hardcoat Hardcoat QA- from 14 to four substrate primer drying zone hardcoat drying zone curing inspection Final assembly QA- Final Transport inspection assembly

CoverForm® Inspection Injection molding QA- Final upon delivery CoverForm® inspection assembly

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The CoverForm® Competence Center in Darmstadt (Germany)

CoverForm®: One-Step In-Mold Scratch Resistance for PMMA

mobile phone display, the panel on a household people at KraussMaffei AG in Munich. At the time, this appliance, and the speedometer cover in a car all machine manufacturer was further developing the RIM tech- have something in common: They are made of nology to mold microstructures on optical media (Blu-ray transparent plastics. Mechanically, their surfaces DVD) using low-viscosity fluids, and was on the lookout for Aare subjected to tough punishment. Chemically, they are a suitable­ material. often challenged by cleaning agents and hand creams. If the plastic fails to resist attack, transparency, and thus function, …to joint product in just two years are undermined. For PLEXIGLAS® parts to stand up to these kinds of tough conditions, they are coated with a scratch- After only one year, the collaboration yielded an initial con- resistant film that also provides high resistance to chemicals. cept study, which both companies introduced jointly at the After the injection molding machine has made the part, K 2007 plastics trade show under the name CoverForm®. it typically goes straight to the coating line. Taking into ac- The new technology attracted enormous interest in areas as count quality checks and transport, the process includes no diverse as automotive engineering, electronics, and house­ fewer than 14 steps from molding compound through injec- hold goods. tion-molded part to the finished and coated plastic part for Spurred by this success, the two partners readied the final assembly. CoverForm® technology, however, reduces concept to mass-production within a few months. One tech- the steps in this value chain to just four: incoming inspec- nical challenge was sealing the entire system, for example. tion, CoverForm® injection molding, quality control, and final assembly (fig. 1). All four steps occur in an in-line pro- Integrated solution cess and, what is more, in the same machine, which saves time, costs, and space. Moreover, the plastic surfaces thus All problems were solved, and Evonik and KraussMaffei produced are in many cases more scratch resistant than tho- jointly launched the technology on the market as a system se that have been coated in the traditional way. solution under the name CoverForm® in 2009. This consists of the injection molding machine, PLEXIGLAS® cf molding From concept… compound, the Reactive Liquide cf 30A reactive system for coating, and the part-specific mold. The concept of CoverForm® was developed by scientists at The CoverForm® process requires special PLEXIGLAS® Evonik‘s Performance Polymers Business Unit nearly four molding compounds developed by Evonik, which are desig- years ago. They wanted to coat the injection molded part nated by the suffix “cf,” and their additives must satisfy cer- right in the injection molding machine, as in the RIM (reac- tain specification limits. The solvent-free reactive system tion injection molding) process in polyurethane processing. consists of two components based on multifunctional (meth) Searching for a suitable partner, Evonik found the right acrylates. The injection device meters the reactive >>>

elements30 evonik science newsletter 19 solution from a small storage flask into the mold with micro- Streamlining adds value liter accuracy. Curing is done thermally in the CoverForm® mold and also by UV radiation after removal from the mold. The CoverForm® process thus incorporates the reactive In the actual process (fig. 2), the mold closes at the start steps into the injection molding process. Production cycle of the cycle. As is usual for injection molding, the plastified time is therefore longer than for “ordinary” injection mold­ PLEXIGLAS® molding compound is injected into the cavity. ing because the machine is occupied by each molded part for While the melt is cooling and solidifying to form the molded a longer period; this reduces throughput and appears at first part, the mold continues to exert pressure on the melt in the sight to be an economical disadvantage. But if viewed as a cavity. single whole comprising both injection molding and coating, The cavity then expands, the injector meters in the reac- the process proves to be unusually efficient because it reduces tive solution, and the mold compresses the cavity once again. the number of process steps necessary from 14 to four. Crosslinking of the reactive solution is initiated under pres- CoverForm® saves plastics processors the high capital sure by a brief heat pulse, and the acrylate system is cured costs of an additional coating line. Those who lack the finan- on the surface of the molded part. The mold is then opened cial resources for their own coating line, and have as a result and the robot removes the molded part and places it on a been outsourcing the production of molded parts, can now conveyor belt. Under UV light the coating film is then com- save themselves the logistical effort and expense involved. pletely cured in-line on the belt in a matter of seconds. Both benefit overall from the new technology, and even the

Figure 2 The CoverForm® process

Injection of Cooling Expansion of Compression Opening Closing Plexiglas® phase mold cavity and reaction of mold of mold phase Compression Injection of Cooling of Removal of and holding reactive system cavity molded part pressure phase

Injection molding process Reaction process Reaction process Injection molding process

Figure 3 Comparison of thermal curing Thermal systems CoverForm® UV-systems systems, UV curing systems, and CoverForm® coating Multifunctional acrylates, often Crosslinking siloxanes Multifunctional acrylate modified with siloxane

Heat curing Curing by heat and UV-radiation UV-curing at room temperature

Contain solvents Free from solvents and siloxanes Contain solvents

Offline process Inline process Offline process

Efficiency 20-95% Efficiency 99% Efficiency 20-95%

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smaller plastics processors can now produce cured PLEXIGLAS® cost effectively in their own machines by using CoverForm® put to the test the CoverForm® system solution. The injection molding machine can also be used for con- Pencil hardness test. With a pencil hardness of 7H, the ventional injection molding if, for example, parts with a CoverForm® coating of PLEXIGLAS® 8N cf is harder scratch resistant coating are not required. It is even possible than PLEXIGLAS® 8N (5H) and PLEXIGLAS® 8N with to run two production lines for a single part: a higher grade acrylate-based UV coating (6H), and many times harder than line delivering a coated surface and a second, less expen­ polycarbonate with a siloxane coating (H). sive, one without this feature. Because the CoverForm® Taber test. The CoverForm® coating yields good results machine allows fast batch changes, moreover, the customer comparable to those for conventional coating systems. can respond to the market flexibly—and, because he has the Scratch hardness test (Erichsen 413). The CoverForm® complete process under his roof, at no great expense. coating resists damage caused by the scratching tip at low as The CoverForm® injection molding machine also scores well as high loads, whereas the other systems become on its footprint. Thanks to its compact structure, it needs no damaged. more than 100 square meters of space, as opposed to the Sand trickling test. The CoverForm® coating here yields 1,000 square meters necessary in the conventional produc- results as good as those for the crown glass used as the tion process for injection molding machine and coating line. standard. Ball indentation test. The CoverForm® coating yields good Invisible curing results similar to those for the two other PLEXIGLAS® samples: The CoverForm® composite, consisting of a hard film on a CoverForm® coating has been designed as an in-line process. hard undercoat, withstands the imposed stress. By contrast, The specially developed reactive solution is solvent- and the hard siloxane coating on the soft polycarbonate undercoat siloxane-free, and is metered to microliter accuracy. This ruptures under pressure, similarly to a thin glass plate on a means that it is not necessary to flood the mold or recycle sponge. excess coating material—unlike conventional thermal coat­ PV 3964 suntan lotion and hand cream test. The CoverForm® ing systems. The coating is crosslinked and cured thermally coating does not react at all with the creams over a period as well as by UV radiation. Thermal crosslinking alone of 24 hours at 80°C in a drying cabinet. The surface shows no achieves an efficiency of 95 percent, which UV curing then damage and the scratch resistance remains entirely unaffected. increases to 99 percent (fig. 3). The coating thickness is nor- By contrast, the surfaces of most plastics and coatings are mally about 20 µm but can be varied between 10µm and damaged in this test. 50µm. Alternating climate test. The CoverForm® coating withstands The pilot plant mold produces 100mm x 100mm sample a large number of load cycles at various humidities and sheets of various thicknesses, which can be used in all the temperatures between –40°C and 95°C. usual tests for scratch resistance and chemical resistance. To get a more accurate picture of the surface properties, Evonik and KraussMaffei’s scientists subjected the samples to various scratch resistance tests and compared them with The scratch hardness test (Erichsen 413) impressively shows how mechanically durable CoverForm® parts can be other PMMA surfaces—PLEXIGLAS® 8N and PLEXIGLAS® 8N PLEXIGLAS® 8N acrylate-based UV coating—and with siloxane coated poly- PLEXIGLAS® 8N cf with CoverForm® carbonate. Hardness tests and suntan lotion and hand cream PLEXIGLAS® 8N cf with acrylate-based UV coating tests show that the CoverForm® coating is extremely resistant Polycarbonate with polysiloxane coating to scratch­ing and chemicals. In composite tests such as the Penetration depth [µm] ball indentation test and the alternating climate test, 0 CoverForm® has proved notably superior to other coating -5 systems. The reason is that no adhesion promoter is needed -10 for CoverForm® coat­ing because compound and coating are precisely matched to each other. -15 This special feature of the CoverForm® coating is very -20 clearly seen in a scanning electron micrograph of a cryofrac- -25 ture in a workpiece broken after liquid nitrogen cooling. The PMMA substrate and the CoverForm® film have the -30 same refractive index of 1.49. There is therefore no deflec- -35 tion of the light beam at the interface between substrate and -40 coating film. In micrographs, the film is not distinguished from the substrate, and is “invisible.” By contrast, a com- -45 mercial-grade polysiloxane coating on polycarbonate is vis­ 0.5N 1N 2N 3N 4N 5N 6N 7N 8N Bearing force [N] ible on a cryofracture; the phase boundary is clearly >>> elements30 evonik science newsletter 21 The injection molding machine designed exclusively for the CoverForm® process

seen in this case. When a load is applied, the adhesion pro- Even more surface functionality moter ruptures in the middle; in other words, it continues to adhere­ to both substrate and coating film, resulting in what The CoverForm® technology creates PLEXIGLAS® molded is known as a cohesive fracture. Due to the different refrac­ parts and directly produces—in-line and with no change of tive indices of the polycarbonate and the coating film, such mold—a scratch- and chemical-resistant coating. The only parts always have a superficial iridescent shimmer to them, restrictions are that the component to be coated must be which is inherently absent in CoverForm®. moldable and can be coated only on one side. Potential application areas open up wherever high quality CoverForm® for hands-on innovation: coatings are required that must be resistant to scratching The Competence Center in Darmstadt and wear arising from contact with hands, fingers, or hand creams. Examples include automobile interior parts such as Encouraged by the extraordinarily high demand from speedometer and switch covers and panels, watch and clock current and prospective customers, Evonik Industries and glasses, covers of household gadgets, mobile phone and KraussMaffei AG opened a Competence Center in Darmstadt smart phone displays, eyeglasses, and sunshades. in November 2008, allowing them to check out CoverForm® Other reactive systems with new surface functionalities for themselves. Customers can have samples coated and ob- are being developed, with a focus on nonreflecting and elec- serve the process in action. trically conducting surfaces. l During the discussion, the CoverForm® machine, positi- oned near the meeting table, produces samples that custo- mers can take back to their own labs for testing. In this way, customers see first hand that the CoverForm® process is re- liable and simple enough for them to use, and by no means Contact exclusive to chemical industry experts. Training classes and exclusive projects with custom­ers are also available. Sven Schröbel Manager, Business Development, In addition to providing advice and training, the Compe­ ­ Automotive & Surface Design tence Center also serves as a test center for carrying out ma- Performance Polymers Business Unit terials tests and as a platform for further development of the +49 6151 18-4543 [email protected] reactive system.

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+++ VerbundanlageNew binder imparts in Schanghai high gloss komplett and toughness in Betrieb to plasticgenommen coatings

Electronic gadgets are right at the top of consumers’ wish lists, The irreconcilable reconciled and not just for Christmas! Those with housings finished in luxu- The problem, however, is that common glossy plastic coatings are rious piano black are currently in vogue. Until recently, however, relatively susceptible to mechanical stress and chemical attack. gadgets with their glossy plastic skins suffered from a serious de- Cleaning does them slight damage, and they fare poorly when ficit. Their surfaces were particularly sensitive and almost impos­ alcohol-containing cleaning agents are used on them. But that will s­ible to clean without damaging the coating. Evonik Industries has soon be history. With its DEGALAN® VP 1034 F, Evonik has now solved this problem with a new methacrylate resin. developed a methacrylate resin that, when used as a binder, im- It goes without saying that electronic devices like cell phones, parts to plastic coatings exactly those properties that have so far MP3 players, and flat-screen TVs have to function reliably and been considered irreconcilable: a high-gloss surface combined with well, but, at the same time, they also need to look polished and good resistance to cleaning agents. The substances responsible for chic and embody the latest styles, because a sophisticated appear­ these desirable properties are specialty monomers. ance is a sign of quality—and helps the item sell itself. A growing The binder was developed mainly for the high-end market, in number of buyers think it important, for example, that a flatscreen other words, for the high-quality plastic coatings used for cell TV blend harmoniously into a contemporarily furnished living phones, designer stereo systems, and flat-screen TVs. The binder room, yet stand out as an art object, a conversation piece on ac- can be used in either a single-coat or two-coat process. count of its elegant design. In the single-coat process, only one coat is applied on the sub- For flat-screen TVs, the trend these days is classic black—to strate, usually a less substantial plastic mix. The coating must then be sure, piano black—a glossy plastic coating that conveys virtu- perform two functions: ensure bonding to the underlying plastic ally the same quality as an expensive concert grand piano. Nearly as well as provide aesthetic appeal. In the two-coat process, a coat all major television set manufacturers are clearly partial to piano based on the new binder is applied for the color and is overlaid by black in their product range, aware as they are that the appear­ a clear coat based on UV-curable or polyurethane systems for a ance of a TV set, in addition to the electronics it houses, plays a glossy effect—as in the case of piano black. major role in buying decisions. In addition to these properties, coatings containing the binder have excellent weathering resistance. Moreover, the product can

Consumers want electronic gadgets like cell phones also be used in metalization processes, which make it possible to and flat-screen TVs not only to function reliably, produce metallic reflective coatings. It is also suitable for gravure but also look good. A new methacrylate resin from inks such as those used for printing on packaging films. Evonik now makes it possible for glossy plastic coatings to withstand cleaning agents

elements30 evonik science newsletter 23 +++ Thirty years of VESTOPLAST®

VESTOPLAST® is celebrating its birthday. For 30 years, this prod­ global demand. “In the growth region of Asia in particular, we can uct family from Evonik‘s Coatings & Additives Business Unit has point to very healthy growth rates, even in the current global been lending hot-melt adhesives their reliable bonding strength. economic­ downturn,” remarks Mindach. The range of applications is broad—as an adhesive in diapers and Since 1981, the product has also found application in road con- an additive in road marking materials, and for use under carpeting struction. Asphalt treated with VESTOPLAST®, for example, can or in furniture construction, to name only a few. absorb higher initial stresses and disperse them more rapidly. As a The substances for which the VESTOPLAST® brand name result, road surfaces remain in good condition, even in sweltering stands are co- and terpolymers of ethylene, propylene, and 1-bu- heat or freezing cold. The product is used in road markings, col­ tene. In combination with synthetic resins, these polyolefins have ored sealing compounds, drainage openings, and bitumen sealing excellent adhesive power. When combined with waxes, they also sheets, too. Another important plus point for these environment­ lower melt viscosity and enhance the water vapor barrier effect. ally friendly polyolefins is their 100 percent recyclability. This versatility is important because adhesives today must be cap­ able of far more than creating a durable bond between two sub­ From by-product to commercial success strates. Originally, the products that are so successful today were no more “The main areas of application for our various grades of than by-products in general polyolefin production. Their spectac­ VESTOPLAST® are currently thermoplastic hot-melt adhesives ular rise began in the 1970s, when it became possible to improve for diapers, the wood and furniture industries, and the paper and the quality of the thermoplastic polymer significantly and market packaging sector,” says Dr. Lutz Mindach, head of marketing and research predicted increasing demand. The greatly superior prop­ technical service for Adhesive Resins. “But the product‘s environ- erties of VESTOPLAST® based hot-melt adhesives, compared to mental compatibility is increasingly extending its use in automo­ the polymers used until now, led to this completely new applica- tive interiors and in carpet applications.” Capacities have been tion area. systematically expanded over the last few years to meet growing Following its successful development, the company began, in 1981, exclusive production in what used to be the polybutene plant. Capacity was gradually increased from the initial 12,000 metric tons to the present 70,000 metric tons, with expansion of the single production line to four. Today, the product group com- prises about 16 different grades for a wide variety of application areas. “For the future, we want to expand into new fields of ap- plication—with functionalized types, for example—so that we’ll be far less at the mercy of economic fluctuations in individual branches of industry,” says Mindach.

The adhesive tester is used to determine open time and setting time for adhesives under constant conditions. Both are important parameters for adhesives

+++ Evonik acquires Eli Lilly‘s U.S. Tippecanoe manufacturing site

E vonik Industries has acquired Indianapolis, Indiana-based Eli Lilly “The pharmaceutical market is attractive, economically stable, and and Company’s Tippecanoe Laboratories manufacturing facility produces growth rates near the double-digit range every year.” in Lafayette, Indiana. The site, which employs about 700, manu- In addition to the acquisition of the site, Evonik and Lilly will factures active pharmaceutical ingredients (API) and precursor also enter into a multi-year supplier agreement for active pharma­ materials for the pharmaceutical industry. The Tippecanoe plant ceutical ingredients and intermediates. “We look forward to will be fully integrated into Evonik’s global production and market­ working closely with Lilly, a world-class pharmaceuticals compa- ing network. ny,” explained Dr. Hans Josef Ritzert, the head of Evonik’s Exclu­ ­ “The acquisition of Tippecanoe Laboratories enables us to sive Synthesis & Amino Acids Business Line. “We will be produc­ meet the growing demand for intermediates and active pharma­ ing ingredients for Lilly and other pharmaceutical companies in ceutical ingredients in the pharmaceutical industry and substan­ ­ accordance with the exacting Good Manufacturing Practices tially boosts our global exclusive synthesis business,” said Dr. (GMP) quality standards. Our customers benefit from the tech- Klaus Engel, chief executive officer (CEO) of Evonik Indus­ ­tries. nology portfolio of Evonik’s sites as well as from our expertise in

24 elements30 evonik science newsletter news

the production of pharmaceutical intermediates.” In addition, Evonik access to customers in the pharmaceutical industry. This has al­ has many years of experience in following official and patent law lowed Evonik, which is the first western supplier to implement requirements for patented intermediates and active pharmaceu­ horizontal integration in exclusive synthesis, to position itself prom­ tical ingredients. inently.­ “This announcement represents a positive outcome for em- Evonik’s Asian sites manufacture precursors and inter­mediates ployees at the site, the Lafayette community, and Lilly,” said John as well as non-patented compounds at competitive costs. In addi­ Lechleiter, Ph.D., Lilly’s chairman and chief executive officer. tion, the western European sites – and in future the Tippecanoe “Evonik is a well-established multinational company with a strong facility – focus on refining intermediates and patented active phar- track record in producing high-quality products.” maceutical ingredients. This represents another mile­stone in the Evonik maintains pharmaceutical facilities in Europe and Asia consistent global implementation of the company‘s exclusive syn- and has established a global distribution network with excellent thesis strategy.

+++ Joint venture established for manufacture of glass lenses for LEDs

Evonik Industries and Taipei, Taiwan-based Cristal Material Cor­ entire supply chain in the growing LED market,“ added Wohl­hau­ po­ration have formed a new joint venture to manufacture high- ser. The lenses produced by the joint venture will be sold to LED quality glass lenses for next-generation LEDs, which will mar­ manufacturers. keted under the Savosil™ brand. The Evonik Cristal Materials The LED lenses will be produced using Evonik‘s patented Corporation joint venture will complement Evonik‘s strategy as a SiVARA™ Sol-Gel technology, which allows glass lenses of con- solution provider to the lighting industry while providing Cristal sistent quality to be manufactured in any desired shape. The pro- Material Corporation access to a highly innovative market. cess recently received the Frost and Sullivan European Technology „The LED market will see many new areas of application open Innovation Award. up. Evonik Cristal Materials Corporation will help its customers Compared to conventional light sources, such as incandescent develop new technologies faster, technologies such as UV LEDs lamps and energy-saving lights, LEDs are much more energy ef- to sterilize water, LEDs in automobiles, and LEDs for general ligh- ficient, last longer, and offer many new design possibilities. ting,“ said Patrik Wohlhauser, chairman of Evonik Degussa GmbH‘s Because of these advantages, LEDs are increasingly used in many management board. „Participating in the joint venture offers different lighting applications. For these reasons, Thomas Her­ Evonik an attractive opportunity for forward integration along the mann, head of Evonik‘s Inorganic Materials Business Unit, sees great business opportunities, „The LED evolution is here, with market growth rates expected to exceed 20 percent. We strongly believe LED will become an everyday effective lighting solution and allow everyone to contribute to reduced energy consump­ ­ tion.“ This growth in demand for LED is driven by the Green Lighting trend—in other words, lighting marketed as environ- mentally friendly. Underlying legal conditions, such as banning in- candescent light bulbs or legally requiring cars to drive with lights on during the day will also help this positive development. Ershien Tsai, chairman and founder of Cristal Material Cor­ poration, shared this view. „Glass produced by the SiVARA™ Sol-Gel technology is an ideal LED optics solution and is highly reliable,“ said Tsai. It also offers the phosphorous in the lenses outstanding protection against humidity and heat during opera­ tion and is thus ideal for outdoor lighting. Tsai is pleased with the cooperation and the speed with which Evonik formed the joint venture.

Glass lenses produced using Evonik‘s patented SiVARA™ Sol-Gel technology elements30 evonik science newsletter 25 a M i no A c i d s f o r S p e c i a l t y A pp l i c a t i o n s

Bright Prospects for White Biotechnology

Dr. Andreas Karau

Whether as important components of life- saving IV solutions or chiral building blocks for drugs, amino acids are indispensable. But pre- paring them in enantiomerically pure form is an art: The synthetic route is in many cases exceedingly complex and financially unfeasible; extracting them from protein hydrolysates is, following the BSE scare, no longer acceptable and in any case offers no access to non-natural amino acids. On the other hand, bacteria con- vert renewable raw materials like sugar into amino acids apparently very easily and, more­ over, work under eco-friendly conditions if they get the right blueprint for doing their job. Evonik is master of this art. Since the company switched just four years ago to fermentation­ as the production process for specialty amino acids, the product palette has expanded to 14 amino acids today.

Downstream processing of amino acids at Evonik’s site in Ham (France)

s essential building blocks for proteins and pepti- are then covered by IV solutions. Second, amino acids serve des, amino acids are indispensable to life. Human as dietary supplements in, for example, baby nutrition or and animal nutrition, active ingredient synthesis sports nutrition, to ensure that the body receives an ade­ for drugs, and a variety of technical applications quate supply of the essential amino acids it needs for growth Aare inconceivable without them. Adding pure amino acids to and energy generation. animal feeds can drastically reduce the need for complex Furthermore, amino acids are important building blocks amino acid sources such as fish meal and soybean meal, for pharmaceutical active ingredients. Essential drugs for which in turn goes a long way toward conserving natural re- treating high blood pressure, diabetes, HIV infections, and sources (see elements 28). bacterial infections contain amino acids as building blocks. In the field of human nutrition, two main application areas Amino acids are also being increasingly used in cosmetics exist. First, amino acids are used in clinical nutrition when and in technical applications, for example, as formulation aids patients must be fed parenterally, that is, by-passing the in- or complexing agents as in chemical mechanical polishing­ in testinal tract; their complete daily amino acid requirements the semiconductor production.

26 elements30 evonik science newsletter B I otec H N o l o g y

Bright Prospects for White Biotechnology

amino acids were initially produced by its wholly owned French subsidiary Evonik Rexim SAS by extraction from protein hydrolysates, a source providing access to 15 differ­ ent amino acids. This protein source is of animal origin, however, and with the emergence of the debate on BSE and avian flu this production process, although scientifically prov­en to be safe, lost favor with customers. Moreover, some amino acids such as L-methionine, L-tryptophan, and L-ornithine were not accessible by this route because they are not stable under the hydrolysis conditions of the extrac- tion or are present in the hydrolysates only in very small quantities. As a result, in 2005 and 2006 Rexim switched entirely from extraction to fermentative and biocatalytic production processes. Since that time it has continuously been expand­ ing its product portfolio, which includes both naturally and non-naturally occurring amino acids as well as amino acid derivatives (fig. 1). A major advantage here is that Rexim is fully backward integrated for all important amino acids, through either biocatalytic or fermentative processes. Back­ ward integration in this context means that Evonik controls the entire process chain: Fermentation and downstream pro­ cessing of the crude amino acids as well as the subsequent fine purification are carried out at Evonik sites. Biocatalytic processes such as production of L-methionine by racemate resolution of D,L-methionine have now been established on an industrial scale at the Wuming site in China, where they have been running successfully for many years. For the fermentative processes, Rexim invested in 2006 in its own fermentation and downstream processing line at its affiliate Evonik Fermas s.r.o. in Slovakia. Here the amino acids are fermented and, in some cases, further pro- >>>

Above average growth rates Figure 1 Timeline for introduction of fermentative or biocatalytic production processes for various amino acids These diverse application fields have one factor in common: L-Hse They are all linked to highly attractive markets with above L-Orn average growth rates between 5 and 10 percent per year, de- L-Trp pending on the application. In the area of specialty amino L-Val L-Ile acids, Evonik, servicing a market of several hundred million L-Thr L-Pro euros, is extremely well positioned: It is among the global L-Ser L-Phe leaders offering the complete spectrum of amino acids for L-Arg various markets and application fields. L-Met L-Lys L-Ala Right from the start, Evonik produced the amino acids L-Asp L-lysine, L-threonine, and L-tryptophan for animal nutrition 2009 Time directly by fermentation. By contrast, many of the specialty

elements30 evonik science newsletter 27 cessed to the crude crystallization stage; final downstream sive rational processes. It was thus able to optimize various processing takes place in Ham, France, or Wuming, China, parameters such as productivity, yield of carbon source, and both of which are Rexim sites. Rexim can thus ensure GMP by-products in the microorganisms systematically. This con- compliant production over the entire production chain and serves resources and also reduces production costs. Figure 3 a high standard of quality for customers, which is required shows an example of how yields and productivities have particularly by the regulated pharmaceutical markets. risen over the last few years and the formation of by-prod­ ucts has continuously declined. Interdisciplinary collaboration as an important precondition for success A new path to ultrapure L-tryptophan

If the amino acids are used in active ingredient synthesis, In addition to ongoing optimization of strains and produc- strict requirements on the purity of the products and the re- tion processes, Rexim‘s Process Research and Development producibility of the manufacturing process must be satisfied. also focuses on expanding the product portfolio. In 2009 An important prerequisite here is effective downstream alone, the company launched on the market three new fer- processing of the amino acid which ensures high purities mentatively produced amino acids: L-tryptophan, L-homo­ simultaneously with high yields. The downstream process­ serine, and L-ornithine. ing efforts depend directly on the efficiencies of the bac­terial L-Tryptophan acts as a natural antidepressant; the amino strain and fermentation process. acid is a precursor of neurotransmitters in the human brain In the past, strain development, fermentation, and down­ that are responsible for a feeling of well-being. It is also an stream processing were often developed sequentially. important building block for derivatives used in, for exam­ Today, Evonik‘s technicians work concurrently on these prob­ ple, animal cell cultures for antibody production. In all these lems in interdisciplinary teams (fig. 2). In this way, findings­ applications, purity is key. from downstream processing trials on critical by-products­ For Rexim‘s scientists, the challenge lay in developing a can be integrated directly into strain and process develop- highly efficient downstream processing process for obtain­ ment. This reduces development costs and time to market. ing from the crude product high-purity L-tryptophan with­ While many companies have optimized their strains ini- out undesired impurities. They solved the problem by means tially by classical random mutagenesis, Rexim, in collabora- of a special crystallization process that allowed the purity re- tion with the biotechnologists of Evonik‘s Bioproducts quirements of various pharmacopoeias to be not only met Business Line, has choosen from the start for more progres- but significantly exceeded.

Figure 2 Figure 3 Interdisciplinary collaboration in strain Effect of strain optimization on development, fermentation, and downstream performance processing saves time and money Performance of original strain Performance of improved strain Strain performance Fermentation performance Biomass

Product

Yield

Byproduct/product ratio

Other amino acids/product ratio

s s 0 20 40 60 80 100 120 140 Percent

Downstream processing performance

28 elements30 evonik science newsletter B I otec H N o l o g y

The fermentation building of Fermas, Evonik’s Slovakian subsidiary, in Slovenska L´up˘ca

First industrial-scale fermentative possibility. Fermentation also has the advantage that the production of L-homoserine L-homoserine so obtained can be produced from renewable raw materials and therefore be classified as a natural product. L-Homoserine, a non-proteinogenic amino acid, is an im- Working in conjunction with biotechnologists from portant synthetic building block for various product groups Evonik‘s Bioproducts Business Line, Rexim succeeded in (Fig. 4). It has so far been possible to produce L-homoserine less than 18 months in transforming a threonine producer in industrial quantities only by following complex chemical into a highly active homoserine producer, notably by sup- synthetic routes using, for example, L-methionine as the pressing the breakdown of L-homoserine to L-threonine in starting material. Rexim‘s goal was therefore to develop a the cell. Employees at the Ham site have extensive chroma- process allowing it to supply the market with large quanti- tographic expertise, dating from the period when amino ties of the amino acid. Because L-homoserine is an inter­ acids were still being obtained by extraction from protein mediate in the biosynthesis of threonine (Fig. 5, p. 30), the hydrolysates. They were therefore in a good position to esta- development of a fermentation process was anO obvious blish a highly efficient recovery process to provide >>> O O HOHO HO OR2 OR2 OR2 O NR1H O O NR1H NRO 1H H2N H N H2N Figure 4 O 2 O O OH HO Important molecules thatOH have OH O OR2 L-homoserine asH startingNHBoc material N H NHBocH NHBocO HO NR1H N H N OR HH2N H O 2 O OH NR1H H2N O H NHBoc Protected N OH L-homoserine derivatives H H NHBoc N CO H H2N O H CO2 H H2N HBuilding2N block for Telcagepant O CO2H 2 O (S)-3-Aminopyrrolidine (Migraine drug) HOHO HO OH N N O OH OH N R O O NH R R H N NH2 CO2H 2 NH2 O 2

HO CO H H2N O OH N 2 O R (S)-3-Aminotetra- HO NH2 Azetidine carboxylic hydrofuran L-HomoserineOH acidN derivatives O R NH2

O O H2N O H N H2N 2 O O O OR2 O OR2 OR2 O H2N OO H N H2N H NR1H O O 2 H NRH1H NRO 1H (S)-Hα2-AminobutyrolactoneN L-Aspartic acid semialdehydeO derivatives S S O OR2 O (S)-3-Aminotetra-S H2N H2N O hydrothiophene O H NR1H OR2 O H N O 2 S H NR1H elements30 evonik science newsletter 29 S high-purity L-homoserine in high yield. The process has al- Dr. Andreas Karau ready been transferred to the multi-ton industrial scale. This Born 1967 Andreas Karau is responsible for process research, makes Evonik the first company in the world to offer on the development, and quality assurance for the Product­ market large quantities of fermentatively produced L-homo­ line Rexim and currently located at Evonik Rexim serine of very high purity. SAS, an Evonik affiliate in Ham, France. He studied process engineer­ing at RWTH Aachen, and in 1997 obtained a doctor­ate from the Institute for Enzyme L-Ornithine directly from sugar Technology of the Heinrich Heine University Düssel­ dorf, where he worked in the research group of Prof. Maria Regina Kula. He then joined Evonik, L-Ornithine is a proteinogenic amino acid that plays an im- where he occupied a variety of posts. In the Biotech­ portant role in the human body’s nitrogen metabolism. The nology Project House, he was responsible for establishing the test center and amino acid and its salts are therefore used for patients with transferring processes from the laboratory to the pilot scale. In early 2004 he moved to the ProFerm Project House, which he headed from the end of 2005 impaired liver function to stabilize liver function. The clas- to its successful wind-up a year later. Following a position as senior project sical process for producing L-ornithine is by chemical or en- manager in Evonik‘s Bio Science-to-Business Center in Marl, he took up his zymatic conversion of L-arginine. current post at the start of 2008. +33 323 81-4762, [email protected] In a project carried out with the Science-to-Business Center Bio of Creavis Technologies & Innovation Evonik‘s technicians­ wanted to replace this process by a fermentative process that would allow L-ornithine to be pro­duced directly from sugar. They achieved this goal by using molecular biological processes to analyze a parent strain obtained by classical mutagenesis, and then removing bottlenecks. In this way they were able to more than double the efficiency cost efficiently to market requirements. That this prodigious of the bacteria. Industrial production of L-ornithine started achievement—the transformation was effected in just two- at Fermas last year. and-a-half years—has paid off is evident from the significant- Barely four years ago Evonik achieved a complete trans- ly expanded product portfolio: Evonik now covers the entire formation in production technology for specialty amino acids, spectrum of amino acids for specialty applications, and (in moving from an extraction process to fermentation, which is contrast to extraction of protein hydrolysates, which always more accepted in the customer industries. This established a involves coproduction) can flexibly adjust production capac­ sustainable base allowing the company to react rapidly and ities for individual amino acids according to demand. l

Figure 5 L-Homoserine is an important intermediate in the biosynthesis of L-threonine O Sugar HO OR2 O NR1H H2N O OH H NHBoc N L-Aspartate H

L-Lysine CO H H2N O 2 HO OH N O R NH2

L-Methionine L-Homoserine L-Threonine

O H N 30 2 O elements30 evonik science newsletter OR2 O H N O 2 H NR1H

S news

+++ Evonik at Auto Expo India

Evonik Industries exhibited at this year’s Auto Expo India in New drawing numerous visitors were interior and exterior parts made Delhi. The Chemicals Business Area of Evonik and its Automotive of plastic. On the outside of a car, they feature excellent UV resist­ Industry Team exhibited in the German Pavilion at India’s major ance and weatherability. They also lower fuel consumption and automotive trade show. Extending across some 140,000 square thus CO2 emissions. meters of space, the trade show hosted 2,100 companies from “The German exhibit isn’t showing any signs of crisis,” com- more than 25 countries, who showcased their products to some mented Sven Augustin, Technical Marketing and Innovation Ma­n­ 1.8 million visitors. The theme of this year’s Auto Expo India a­ger at Evonik’s Automotive Industry Team. “On the contrary: “Mobility for all with focus on green technologies.” The country’s pavilion at Auto Expo India has grown by 40 per- India is a heavyweight on the automobile market: It is the cent compared to 2008, and over 2,000 exhibitors presented fourth-largest commercial vehicle market and the eleventh- component parts. Germany and China even had their own halls.” largest automobile market in the world. What is more, except for Augustin said that German suppliers had excellent exhibits and China, India is the industry’s only booming automobile market, vis­ited with very high interest for local manufacturer. As regards with growth at 3 percent. In this connection, exports will play an green technology, local manufacturers like Tata displayed fully increasingly crucial role. The region’s manufacturers have acted electrified vehicles for the first time. “Indian automobile manufac- with this trend in mind, tripling their passenger car exports from turers are one leap ahead in performance and design and will be- 2002 to 2007, quintuple truck export. gin selling their new models immediately. They are open to co- Evonik was present for the first time, along with 30 other operation with German companies. Often, our Indian customers Germany suppliers, in the German Pavilion. The focus here was even have their headquarters in Europe,” confirmsA shok Bandella, on fuel savings, thus echoing the theme of the event. Accordingly, technical market manager at Evonik Degussa India. Evonik’s automobile expertise was met enthusiastically. For ex- The automotive sector is Evonik’s second-largest market and ample, the company’s innovative fillers for low rolling resistance generates annual sales of around €2 billion (2008). The company tires were presented; they make it possible for motorists to save supplies a wide range of products for the sector—from specialty up to 8 percent in fuel consumption. Fuel lines made of Evonik’s chemicals for the manufacture of fuel-saving tires, high-perfor- special plastics are, by virtue of their durable properties, thinner mance plastics for fuel and coolant lines, oil additives, and plastics and lighter and thus more easily formable than common systems components for automotive interiors to lightweight bodywork of metal or elastomers. They also lower weight considerably. Also and scratch-resistant high-gloss coatings.

+++ More than 300 VESTAMID® offshore lines in three years

Since its approval in mid-2006, VESTAMID® LX9020, a polyamide 12 mold­ ing compound made by Evonik Industries, has been used in the manufacture of more than 300 non-bonded flexible pipes in the oil industry. Oil com­ panies are already using the pipes in offshore projects. The molding compound was tested over a two-and-a-half year period between 2003 and 2006. These studies confirmed its advantageous proper- ties over other polyamides used as barrier layers in flexible piping, properties that are crucial to the compound’s success. In collaboration with Wellstream International Limited, Evonik has conducted intensive tests to demonstrate compliance with the international standards API 17J (for flexible pipes) and ISO 13628-2. The tests evaluated creep performance, ductility, thermal ex- pansion, methanol compatibility, and hydrolysis resistance as plus points. On the basis of these results, Lloyd’s Register granted Wellstream approval in June 2006 for the use of the polyamide 12 molding compound VESTAMID® LX9020 in the manufacture of flexible pipes for conveying production and in- jection fluids in offshore crude oil production, giving the company the award of the Certificate of Material Qualification for the Use of Polyamide 12G rade VESTAMID® LX9020 in Non-Bonded Flexible Pipes. Since then, the molding compound has been used commercially for the manufacture of flexible pipes. The polyamide 12 grade specially developed Developed specifically for offshore for the purpose combines the above technical advantages with consistent applications: the new Polyamide 12 grade VESTAMID® LX9020 product quality; this ensures outstanding processability, thereby reducing setup­ times, scrap, and the risk of extrusion faults. elements30 evonik science newsletter 31 events

Fbruarye 1 0 march 1 0

02/23–02/24/2010 16.12.–21.12.200703/07–03/10/2010 03/10–03/12/2010 03/14–03/19/2010 10th Colloquium: Joint Research on International10th European Symposium Symposium on 43rd Annual Meeting of EUCHEM Conference on Adhesive Technology Catalysison Polymer & FineBlends Chemicals German Catalysis Experts Molten Salts and Ionic Liquids 2010 frankfurt/main (germany) dresdensingapur (germany) weimar (germany) bamberg (germany) events.dechema.de www.ipfdd.dewww.cfc2007.org/index.html www.processnet.org/ http://events.dechema.de/ katalytiker2010.html euchem2010.html

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04/07–04/10/2010 05/02–05/07/2010 05/13–05/15/2010 POLYCHAR 18 – World Forum EUCHEM Conference on Bunsentagung 2010 for Advanced Materials Stereochemistry bielefeld (germany) siegen (germany) brunnen (switzerland) www.bunsen.de http://polychar18.uni-siegen.de www.stereochemistry- buergenstock.ch

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06/02–06/04/2010 06/07–06/11/2010 08/29–09/02/2010 Nanotoxicology 2010 Formula VI – Formulations 3rd EUCheMS Chemistry Congress edinburgh (united kingdom) for the future nürnberg (germany) www.nanotoxicology2010.org/ stockholm (sweden) www.euchems-congress2010.org www.chemsoc.se/sidor/KK/ formulaVI/index.htm

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09/13–09/15/2010 10/03–10/05/2010 ORCHEM 2010 Polydays 2010 – Polymers in weimar (germany) Biomedicine and Electronics www.gdch.de/orchem2010/ berlin (germany) www.gdch.de/makro2010/

Credits Design Michael Stahl, Munich (Germany) Publisher Evonik Degussa GmbH Photos Innovation Management Evonik Industries Chemicals & Creavis Karsten Bootmann Rellinghauser Straße 1–11 Dieter Debo Evonik Industries AG 45128 Essen Markus Schmidt Rellinghauser Straße 1–11 Germany Stefan Wildhirt 45128 Essen Fotodesign Lichtblick/ Scientific Advisory Board A. Langosch (p.13) Germany Dr. Norbert Finke Daskleineatelier/ www.evonik.com Evonik Degussa GmbH Fotolia (p.16) Innovation Management Justin Horrocks/ Chemicals & Creavis iStockphoto (p.18) [email protected] Stormarn/Fotolia (p.31)

Editors Printed by Dr. Karin Assmann Laupenmühlen Druck GmbH & Co.KG (responsible) Bochum (Germany) Evonik Services GmbH Editorial Department Reproduction only with permission [email protected] of the editorial office

Contributing Editors Evonik Industries is a worldwide Klaus Jopp manufacturer of PMMA products sold Dr. Angelika Fallert-Müller under the PLEXIGLAS® trademark Michael Vogel on the European, Asian, African, and Australian continents and under the ACRYLITE® trademark in the Americas