Nexam Chemical and Evonik – Competition or Collaboration?

Posted: 20 June, 2015 in Nexam, Published Investment Calls
Tags: , , ,

Nexam and the Nexam technology / future expected impact has previously been highlighted here:

https://cuttingedgescienceinvest.com/2014/09/28/nexam-chemical-nexam-genius-applications-of-the-148-year-old-berthelot-reaction/

https://cuttingedgescienceinvest.com/2015/03/28/nexam-full-scale-tests-in-a-double-digit-growth-industry-the-global-plastic-pipes-market/


Logically, within the cutting edge polymer cross linking research area, confidentiality and confidentiality agreements lowers the accuracy of outsider speculation. Furthermore, it is difficult to decipher the relationships between the major key market leaders.  Very recently, one or several Placera bloggers (Placera = A Swedish stock market forum) suggested that a near future joint Evonik-Nexam webinar together with joint sales of a specific molecule (PBO), could be potential clues to an ongoing Nexam-Evonik collaboration

PBO= 1,3-Phenylene-Bis-Oxazoline  (Nexam PBO link and Evonik PBO link).

Let´s check the Evonik patent landscape:

Evonik US 20140163165 A1 (published June 12, 2014)

Low molecular weight products and use thereof as reversible or permanent low-temperature crosslinking agent in diels-alder reactions

The invention relates to low molecular mass products and to their preparation and use as reversible or permanent crosslinkers in polymers or polymer networks where the linking or crosslinking of the resultant polymers is brought about via Diels-Alder reactions.

CESI: The Diels Alder reaction is related to the original Nexam cyclotrimerization reaction. Both reactions produce 6 membered rings after heat activation. The Nexam cyclotrimerization produces a substituted benzene ring and the Evonik 4+2 cycloaddition produces a cyclohexene ring. If fully unsaturated rings are desired using Diels Alder methodology (= non reversible cross linking = substituted phenyl derivatives = the Nexam cyclotrimerization target product), the Diels Alder approach is potentially less straight forward and necessitates a post elimination of substituents or (normally) a subsequent oxidation:

Benzene DA

The graphic example above is attached solely to explain how a phenyl derivative can be synthesized via a Diels Alder synthetic sequence. This example is not related to any announced Evonik activities.

However, CESI´s initial conclusion is that Evonik primarily is focusing on reversible low temperature applications using an alternative strategy and primarily within the following areas (as highlighted in the patents final sections):“Adhesive, moulding compounds, inks, sealants, coating materials, composite materials, or use in the production of mouldings for example via rapid prototyping methods. One example of application in the rapid prototyping sector for the crosslinking and uncrosslinking materials described here is to be found in the sector of FDM (Fused Deposition Modelling) or in 3D printing by inkjet methods using low-viscosity melts.”

Reversibility is stated as a strength by Evonik. CESI believes that reversibility equals a limitation of scope. In other words: The Evonik concept might be limited to low temperature special applications. However, the Evonik marketing strategy seems excellent and the market potential for the actual special applications should also be large…

Evonik wants to facilitate bulk production of composites

  • New technology is designed to significantly reduce manufacturing costs for composites
  • Hybrid polymer systems form the technology base and are scheduled to be launched on the market in late 2018
  • In the composites business, Evonik aims for medium-term sales in the lower triple-digit million € range

With a chemical trick, Evonik Industries combines the best from two worlds—the characteristics of two types of plastic which were said to be incompatible until now. In doing so, the specialty chemicals company wants to provide an answer for one of the central questions of the composites industry: How can we succeed in producing composites more efficiently? Composites are made of extremely strong fibers embedded in a polymer (plastic). The polymer primarily determines the composite processing. Hybrid polymer systems are the heart of Evonik’s innovation—they combine good processability of thermoplastic polymers and good mechanical properties of thermosetting plastics.

Composites are already in great demand in many different application fields: In lightweight design in the automotive and aviation industry, for example, they reduce the fuel consumption. According to experts, every 100 kilogram of weight saved in a car saves around 0.3 to 0.5 liters of fuel per 100 kilometers. In wind turbines, composites guarantee enormous stability and make bigger and thus more efficient energy plants possible.

But, the production of composites is still complex and costly. Since late 2014, Evonik demonstrates in pilot plants at its Marl site that the material concept of hybrid polymer systems can save time and costs in manufacturing composites. First potential customers have already received samples for testing. First hybrid polymer systems are expected to be ready for the market in 2018.

“Our technology will help to significantly reduce manufacturing costs for composites,” says Chief Innovation Officer Ulrich Küsthardt with conviction, adding that “We want to contribute to leading the way to bulk production of composites.” Evonik that already offers numerous innovative products for composites wants to continue strengthening its position in this growth market.

The company is aiming for sales in the lower triple-digit million € range in the composites market in the medium term. For the market of carbon fiber-reinforced plastics alone, CCeV, a network of companies and research institutes in the fiber composites field, is expecting stabile annual growth of an average of 9 percent by 2020.

Composites are a key technology for lightweight design because of their ability to combine very good mechanical properties and low weight. Their processing properties are mainly determined by the polymer. Thermosetting plastics have very good mechanical properties but do require longer processing times compared to thermoplastic materials. But then again, thermoplastic polymers are easy to process, quick to reshape and to recycle, however, they rarely demonstrate the excellent mechanical properties of thermosetting plastics.

There is a reason for the very different properties: polymer chains in thermosetting plastics are crosslinked whereas in thermoplastics they are not. Switching between crosslink and no link is usually not possible because a chemical crosslinking process is irreversible.

Special Diels-Alder reaction as chemical switch

However, this is exactly what Evonik achieved in cooperation with the Karlsruhe Institute of Technology in producing hybrid polymer systems. They are able to crosslink without using catalysts in a completely reversible process. Heating causes de-crosslinking and allows the system to be reshaped. During the cooling phase, the crosslink is created again and its shape becomes stabile.

A special Diels-Alder reaction causes this phenomenon where the crosslink is almost chemically switched on and off. Material properties are maintained even with repeated heating and cooling.

“We’re cooperating closely with suppliers of semifinished products, plant producers, and processing companies of fiber-reinforced plastics to develop appropriate processing chains for our hybrid polymers,” explains Sandra Reemers, head of Evonik’s Composites Project House. “We aim at offering system solutions that enable an efficient production process for semifinished products as well as final parts.”

The Composites Project House founded in April 2013 develops new materials, processes, and system solutions for composite materials. Project houses are a part of Evonik’s strategic innovation unit Creavis. In the project houses, the company pools expertise from various operative units, bringing in additional external experts. Together, they research topics that expand the existing product and technology portfolio and advance these projects to application stage.

Company information

Evonik, the creative industrial group from Germany, is one of the world leaders
in specialty chemicals. Profitable growth and a sustained increase in the value of the company form the heart of Evonik’s corporate strategy. Its activities focus on the key megatrends health, nutrition, resource efficiency and globalization. Evonik benefits specifically from its innovative prowess and integrated technology platforms.

Evonik is active in over 100 countries around the world. In fiscal 2014 more than 33,000 employees generated sales of around €12.9 billion and an operating profit (adjusted EBITDA) of about €1.9 billion.

Now, let´s highlight an Evonik patent:

Low molecular weight products and use thereof as reversible or permanent low-temperature crosslinking agent in diels-alder reactions  US 20140163165 A1 (Source link: http://www.google.com/patents/US20140163165:)

The invention relates to low molecular mass products and to their preparation and use as reversible or permanent crosslinkers in polymers or polymer networks where the linking or crosslinking of the resultant polymers is brought about via Diels-Alder reactions.

Methods for the reversible crosslinking of polymers are of great interest for a broad field of applications. In adhesive applications, for example, diverse possibilities for the automotive industry or the semiconductor industry have been described. In the context of the construction of machines, precision mechanical devices, or in the building industry as well, however, such adhesives are of interest.

Besides adhesive applications, reversibly crosslinkable polymers may also be of interest in sealants, coating materials such as varnishes or paints, or in the production of mouldings for example via rapid prototyping methods.

The best-known crosslinker molecules for Diels-Alder crosslinking reactions are the bismaleimide units (COMPIMIDE® from Evonik AG) that have already been available commercially for a considerable time.

For a number of years, primarily within academia, methods for constructing block copolymers have been researched under the generic heading of “click chemistry”. In this chemistry, two different homopolymers with linkable end groups are combined with one another and are joined to one another by means, for example, of a Diels-Alder reaction, Diels-Alder-analogous reaction or another cycloaddition. The objective of this reaction is to construct thermally stable, linear and possibly high molecular mass polymer chains. Inglis et al. (Macromolecules 2010, 43, pp. 33-36), for example, describe, for this purpose, polymers with cyclopentadienyl end groups which are obtainable from polymers prepared by means of ATRP. These cyclopentadiene groups are able to react very rapidly in hetero-Diels-Alder reactions with polymers which carry electron-deficient dithioesters as end groups (Inglis et al. Angew. Chem. Int. Ed. 2009, 48, pp. 2411-2414).

The use of monofunctional RAFT polymers for linking with monofunctional polymers which a dihydrothiopyran group by way of a hetero-Diels-Alder reaction is found in Sinnwell et al. (Chem. Comm. 2008, 2052-2054). This method can be used to realise AB diblock copolymers.

Rapid variants of this hetero-Diels-Alder linkage for the synthesis of AB block copolymers with a dithioester group which is present after a RAFT polymerization, and with a dienyl end group, are described in Inglis et al. (Angew. Chem. Int. Ed. 2009, 48, pp. 2411-14) and in Inglis et al. (Macromol. Rapd Commun. 2009, 30, pp. 1792-98). The analogous preparation of multiarm star polymers is found in Sinnwell et al. (J. Pol. Sci.: Part A: Pol. Chem. 2009, 47, pp. 2207-13).

U.S. Pat. No. 6,933,361 describes a system for producing transparent mouldings that are easy to repair. The system consists of two polyfunctional monomers which polymerize by a Diels-Alder reaction to form a highly dense network. One functionality in this system is a maleimide, and the other functionality is a furan. The thermal switching of a highly dense network of this kind is used for its repair. Crosslinking takes place at temperatures above 100° C. The partial reverse reaction at even higher temperatures.

In Syrett et al. (Polym. Chem. 2010, DOI: 10.1039/b9py00316a), star polymers are described for use as flow improvers in oils. These polymers have self-healing properties that can be controlled by means of a reversible Diels-Alder reaction. For that purpose, monofunctional polymethacrylate arms are combined with polymethacrylates which in the middle of the chain, as a fragment of the initiator employed, possess a group which can be used in a reversible Diels-Alder reaction.

Patent application DE102010001987.9 discloses crosslinkable systems which feature a thermoreversible crosslinking mechanism based on a Diels-Alder or hetero-Diels-Alder reaction. DE102010001992.5 discloses analogous systems which have a controllable viscosity by means of the same thermoreversible mechanism.

U.S. Pat. No. 4,513,125 A discloses a composition for special cathodic electrodeposition coatings, where a polydiene-functionalized epoxy-amine reacts with a polydienophile-functionalized polyisocyanate oligomer at elevated temperatures. The polydienophile-functionalized polyisocyanate oligomers have a functionality of at least 3. Cited specifically are furfuryl alcohol and/or furfurylamine, 2-hydroxymethyl-1,3-butadienes, 2-aminomethyl-1,3-butadiene or mixtures thereof. Sorbic alcohol derivatives, however, are not cited.

Object

“It was an object of the present invention to find low molecular mass crosslinker molecules, easy to synthesize and with diverse possible uses, for Diels-Alder reactions at preferably low temperatures, and with the possibility of a retro-Diels-Alder reaction for reversible crosslinkings, these molecules additionally being particularly ecological.”

[…]

“Surprisingly it has been found that the compounds according to the invention can be crosslinked with dienophiles even at room temperature or at only slightly elevated temperatures and that the crosslinking can be made at least 50% reversible at a higher temperature.

It has been found that these systems crosslink very rapidly even at room temperature, optionally with addition of a crosslinking catalyst. It has also been found that these networks can be returned to a thermoplastic state again, simply and almost completely, even at very low temperatures of, for example, somewhat above 80° C. It has additionally been found, very surprisingly, that subsequently a further crosslinking can take place, without further addition of crosslinker and/or catalyst, by means, for example, of pure cooling. A particular effect, furthermore, is that these cycles of crosslinking and conversion back into a thermoplastic can be carried out at least three times, preferably at least five times, without any substantial loss in properties of the network.”

To the best of the authors knowledge, there are no available information describing a hands on collaboration between Nexam and Evonik (within PBO, cyclotrimerizations or Diels Alder reactions). Therefore, CESI disqualifies this hypothesis until such information is formally released. Thus, to the best of the author´s knowledge and on the molecular level, Evonik pursues an alternative concept and should – until the opposite is announced – be classified as a potential future Nexam competitor primarily within low temperature segments. CESI is fully convinced that the Nexam future is very bright. Reversibility is stated as a strength by Evonik. CESI believes that reversibility equals a limitation of scope. In other words and again: The Evonik concept should be limited to low temperature special applications. Regardless, the total market is gigantic and will allow a number of key market players. Furthermore, CESI believes the near future joint webinar will be beneficial for both Nexam and Evonik. However, the Nexam Evonik collaboration is, as expected, a soft collaboration.

Any marketing Synergy effect? CESI: Yes, most likely.

The last weekend Nexam – Evonik webinar is attached here: http://www.globalspec.com/events/eventdetails?eventid=685&evtsrc=EvonikShare)

At t= 36:45. Moderator:

“We have quite a number of questions so far. I´ll start with Jeff Dimmit:

How are Nexam and Evonik working togheter in this area?”

“We realized in the recent past that our dianhydride products and Nexam cross linkers would be often used in the same or similar applications and by similar customers and it just made sense to give us better coverage in the market place if we could work togheter as a team sharing market information and better service to the market with both of our products”

– Jeff Dimmitt, Vice President of Technology and Business Development Evonik Jayhawk Fine


EDIT September 7 2015 🙂

Press release: Evonik Jayhawk and Nexam Chemical form Joint Marketing Program with focus on Polyimide Solutions.

2015-09-07

Evonik Jayhawk Fine Chemicals Corporation and Nexam Chemical AB have begun a joint-marketing program, whereby Evonik’s JAYHAWK dianhydrides and Nexam Chemical’s NEXIMID® cross-linkers will be offered in a coordinated effort to the growing polyimide market sector.

Evonik and Nexam Chemical will collaborate on modifying and improving polyimide processing, while offering physical and mechanical property enhancements. Customers will benefit from consultation in product selection, pairing and optimal dosing to achieve desired properties of their polyimide coatings, films, fibers, foams and resins.

Said Dr. Jeff Dimmit, VP Technology for Evonik Jayhawk, “Our first collaboration was the “Empowering Polyimides” webinar, narrated by Dr. Carlos Solano, Product Manager for Nexam Chemical. The participation and lively Q&A period frankly overwhelmed us. This positive proof that the industry is thirsty for knowledge on how to use our products together has led us to move into a market collaboration.”

Best regards, CESI

The author, Cutting Edge Science Invest, is a Nexam Chemical share holder. Cutting Edge Science Invest can not guarantee, or take into accountability, the content of truth and accuracy of the information in this article/post. Thus, Cutting Edge Science Invest requires that a possible reader gather complimentary information if any type of investment in the company described above is considered. Cutting Edge Science Invest provides personally biased information and at best also “general information and opinions”. The article/post does not contain professional investment advice. 

Comments
  1. Chris Elland Pehrson says:

    “Furthermore, CESI believes the near future joint webinar will be beneficial for both Nexam and Evonik.” Känns tryggt att ha en kemist som skribent på Placeras forum.

  2. Tack. Lita dock inte på mig. Jag har haft fel förr 😉

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