b u s i n e s s

NEW CATALYSTS RENEW POLYOLEFINS Tailored polymer structures expand market for commodity materials Paige Marie Morse C&EN Houston

There is a buzz among the producers of polyolefins, an unexpected excite­ment that is sweeping through this

more than 100 billion-lb-a-year commodity market. At the center of the fluny is a breakthrough in technology—metallocene or single-site catalysts—that gives produc­ers the power to design precise polymers, a feat that has briefly distracted them from the cost-cutting and price battles typical of a commodity market.

The leader of a company created to ex­ploit this new technology says the indus­try response is at "a fever pitch." Gregory L. McPike, president and chief executive officer of Univation Technologies, a one-year-old joint venture between Exxon Chemical and Union Carbide, says, "It is amazing that an industry this old has that much vitality in it."

With new catalysts and processes, producers can now exercise greater con­trol over polymerization, consistently creating more uniform polymers to meet the performance properties required by their customers. In truth, news about these catalysts has been heard from the technical ranks for many years. But now—with several production units op­erating and technology licenses avail­able—the business colleagues of these early researchers have increased the vol­ume. This laboratory curiosity has finally become a commercial reality.

Shoe soles and tubing ate end uses for new

elastomer products afforded by Dow's Inslte

catalysts.

"The industry now has the ability to take a design approach to poly­mer structure for greater speed and accuracy of development," said Kurt W. Swogger, vice president for polyolefins R&D at Dow Chemical, at the recent Met-Con '98 conference in Houston, spon­sored by the consulting firm Catalyst Group, Spring House, Pa. Dow describes its use of this technology as "molecular architecture."

The crucial next step for this technolo­gy is to access the mainstream polyolefins market and compete with existing materi­als on a cost basis. The high performance

Commodity polymers based on single-site catalysts are on the market Producers

Polymer Malm U.S. Europe

Linear low-density polyethylene

High-density polyethylene

Polypropylene

Film

Film

Fibers, nonwovens

Dow, Exxon, Phillips, Mobil

Dow

Exxon, Fina

BASF/Elenac, Borealis, BP Chemicals

Fina

Targor

Source: Phillip Townsend Associates

offered by these new polymers has already led to opportunities in the specialty mar­kets, but penetration at the large-volume commodity level is required if the produc­ers expect to regain their significant R&D costs. The market and technology devel­opment decisions of companies in the next several months will fundamentally define whether these products truly revo­lutionize the polyolefin market or just pass into the smaller specialty arena.

The term metallocene has often been used to describe these new polyolefin cat­alysts. In the early development, this term was appropriate because most of the cata­lysts were based on metal compounds that included π-bound cyclopentadienyl (Cp) ring structures. Many more types of cata­lyst structures are now being explored and used, so the descriptor metallocene

is being replaced by the |S broader term "single-site cat-•§. alyst"—-because the poly-

l e merization is thought to oc­cur at a single site on the

|ω metal catalyst. Exxon's Exxpol and

Phillips' proprietary cata­lysts—both of which are based on substituted zir-conocene dichloride—are examples of commercial me­tallocene catalysts. In con­trast, Dow's Insite catalysts are single-site catalysts; they have a metal center bound by a single Cp ring that has a bridging group to a het-

eroatom that is also bound to the metal. Much of the new nonmetallocene cata­

lyst developments for olefin polymeriza­tion are due, in part, to "the patent stran­glehold held by Exxon and Dow" in me-tallocenes, says John J. Murphy, program director at the Catalyst Group. In an effort to establish their own intellectual proper­ty, many companies have turned to alter­native catalyst compounds to create simi­lar tailored polymer structures.

Most major polyolefin pro­ducers acknowl­edge that they spend significant resources keep­ing track of com­petitors' activity in this field, and there have been several patent dis­putes. Many com­panies arc licens­ing, or planning

Japan

Mitsui Chemicals, Japan Polyolefin, Sumitomo, Ube

Asahi

Mitsui Chemicals

JULY 6, 1998 C&EN 11

b u s i n e s s

New alliances to address developing technology When C&EN reviewed the developments in polyolefin catalysts three years ago, the company names mentioned were easily recognized by most who work in the chemical industry. Such familiarity is gone. Many companies have created new ventures—with new names—to work in the rapidly expanding field of single-site, often called metallocene, catalysis. Also, many companies have alliances or licens­ing agreements with competitors to strengthen their position in this area.

"There remain very few polyolefin players without a partner, position, or potential in the supply of metallocene-catalyzed materials," says John J. Mur­phy, program director at Spring House, Pa-based consulting firm Catalyst Group.

Exxon Chemical and Dow Chemical continue to dominate this technology, and both have been actively forming al­liances with several other companies. Hoechst also has a strong patent base in the single-site catalysis area that it has leveraged with alliances.

Several of the new ventures cite intel­

lectual property issues as a reason for their formation. Numerous patents have been filed in the single-site catalyst area and several disputes have arisen—many industry participants call the technolo­gy area a "patent minefield." Through an alliance or joint venture, companies can combine their intellectual property estates to create a stronger force.

"The combination of Exxon and Union Carbide has made the patent estate a lot broader and more difficult to penetrate," says Gregory L. McPike, president and chief executive officer of Univation Tech­nologies, the polyethylene joint venture between Exxon and Union Carbide.

Also, in the announcement of the venture, the companies pointed out that "the joint venture resolves current and likely future legal disputes between Exx­on and Union Carbide over ownership of the technology."

The need to respond quickly in this fast-moving technology area is also an important consideration. Often these cat­alyst technologies provide routes to prod-

Univation Technologies

Dex-Plastomers

Mitsubishi Borealis Ube

Eienac <# PE with Shell BASF

PPT

Targor «*- pp

PE

Exxon

PP

Hoechst

Mitsui gi£^°

Montell

γ Dow 4 Elastomers^ DuPont Dow

with DuPont Elastomers

χ BP Chemicals

« » s Joint venture or alliance • s license

PE = polyethylene PP = polypropylene

Source: Catalyst Group

X.PP

Fina PE

ucts in unfamiliar markets. An alliance can facilitate rapid access to a market, be­fore another competitor moves in.

"Dow was looking for an applications and channel-to-market partner" for its ethylene-propylene-diene monomer technology, says Ashby L Rice, vice pres­ident for technology at the joint venture DuPont Dow Elastomers. "DuPont of­fered a long-standing market leadership position, knowledge of the elastomers in­dustry, and a portfolio of strong brands," adds Cathy Branciaroli, director of global communications for the venture.

The extensive resources of the parent companies, available electronically, if not physically, help these ventures develop new products more rapidly. For example, Targor, the polypropylene joint venture between Hoechst and BASF, has access to the research facilities of these companies and often contracts experimental work from their scientists. Hoechst recently an­nounced that it would withdraw from that venture within the next two years, but Tar­gor will continue to have access to techni­

cal expertise through Hoechsts new R&D company, Aventis.

The lines between companies, markets, and technologies are blurring with the myriad agreements among players in the single-site catalyst field. Clarifying the scope of these rela­tionships is a task that takes a lot of effort, say most companies, to ensure minimal overlap. But as this technology progress­es and new uses for these catalysts are found, the boundaries are increasingly diffi­cult to define.

Evolue

Phillips

to license, their technology, and intellectual property is a significant part of the product they offer. Defending their patent base is a fundamental part of business.

Disputes also arise because this tech­nology is expected to have a significant impact on the future markets for polyole-fins. As in most emerging technology ar­eas, establishing a strong intellectual prop­erty base early is an important part of en­suring future success.

Univation's McPike says that with such a "rich technology area," it is not

surprising to have a "feeding frenzy of competitors."

Single-site catalysts differ from conven­tional olefin polymerization catalysts in that the metal atom usually is in a con­strained environment, which allows single access by monomers to this catalytically active site. Polymers grow by a single mechanism, instead of the multiple routes that occur in Ziegler-Natta systems, thus forming a more uniform and reproducible polymer structure. By determining the route and kinetics of the chain growth, a

polymer can be designed for a particular performance target.

For polyolefins, this technology trans­lates to various performance enhancements including increased strength and toughness, better clarity and gloss, and easier and more consistent handling characteristics.

With the improved performance of­fered by tailor-made polyolefins, some of the characteristics of high-end engi­neering polymers can be achieved with potentially inexpensive polyethylene or polypropylene.

12 JULY 6, 1998 C&EN

ΡΕ.

ΡΕ -£S2orners

with union carbide

É

Researcher conducts catalyst R&D In Baytown, Texas, lab.

"Instead of competing with a commod­ity plastic," says Mark Mack, director of polyethylene processes at Equistar, "these materials, based on polyolefins, can com­pete in engineering polymer applications or with a metal. That is very exciting." Eq­uistar, a joint venture of the petrochemical operations of Lyondell Petrochemical, Mil­lennium Chemicals, and Occidental Chem­ical, is the largest U.S. producer of polyeth­ylene (C&EN, June 8, page 22).

Intermaterial competition between the polyolefins is also increasing because of this technology, says Michael Gallagher, marketing and sales director of licensing at Univation. "The lines are blurring between polymers, with polyethylene taking over polypropylene applications, and then poly­propylene taking over engineering plastics applications. The [product] growth chain is going in that direction."

Today, the commercial polyolefins made with these catalysts are linear low-density polyethylene (LLDPE), high-density polyethylene (HDPE), and poly­propylene. In 1997, close to 500,000 lb of commodity polymers worldwide was made using single-site catalysts, accord­ing to Surinder Bahl, a project manager at Houston-based consulting firm Phillip Townsend Associates. The majority was made in the U.S., with small quantities made in Europe and Japan.

Most of these products were not made in facilities dedicated to metallocene, or single-site, catalysts, says Bahl, and produc­tion capacities are not clear. "A producer

can easily retrofit a plant because it does not take too much time, effort, or money to make LLDPE in an existing plant with a metallocene catalyst. At this stage, capaci­ties are very difficult to define for metallo­cene [polymers]." The large size of poly-olefin reactors, typically more than 500 million lb per year, means that little production time is required to prepare ad­equate quantities for today's demand.

Several companies have begun to point out this flexibility in recent years. Most announcements about new or ex­panding polyolefin manufacturing facili­ties note that new units have the capabil­ity to make a metallocene or single-site catalyst polymer product.

At Univation, the realization of this need for flexibility has translated into a unique business opportunity. "What Uni­vation offers—which no one else does—is plant retrofit technology," says McPike. "It allows someone with an older gas-phase plant to apply metallocene technology to it. It does not require a new plant."

Univation licenses Carbide's Unipol polyethylene process technology, which is the global leader in third-party licenses for polyethylene technology. With Uni­pol accounting for 53% of worldwide li­censes, according to the company, Uni­vation has access to more than 100 poly­ethylene reactors.

Phillips Petroleum took advantage of the new flexibility offered by its propri­etary single-site catalysts to make LLDPE, a new product for the company, in reactors that usually are used to make HDPE (C&EN, March 10, 1997, page 12). "We saw the metallocene technology as an op­portunity to lower the density capabilities of the Phillips process," says Don G. Bra­dy, manager of polymers and materials. "From the beginning, we had a very high interest in using the catalysts to produce LLDPE in the Phillips slurry loop process-

both for use internally and for licensing ac­tivities." Brady adds that Phillips started its catalyst licensing efforts this spring.

Single-site catalysts are particularly use­ful for LLDPE production, which copofy-merizes ethylene with various α-olefin comonomers, because the comonomers are incorporated more uniformly than they are with conventional catalysts. The resultant polymers have a narrow molecu­lar weight distribution and predictable physical and mechanical properties.

Equistar's Mack says his company's cat­alyst development efforts are focused on LLDPE for this reason. "The comonomer efficiency advantage is twofold. First is the ability of the catalyst to easily incorporate the α-olefin into the ethylene polymeriza­tion without reaching a plateau [in incor­poration rate]. Also, the catalysts place the comonomer evenly throughout the back­bone, not just in the low molecular weight zone," Mack explains.

Equistar has a significant position in the LLDPE market, but it does not yet offer a single-site-made polymer. Mack reports that pilot-plant efforts and a few customer trials are in progress. Equistar is consider­ing licensing its proprietary catalyst tech­nology, which uses a heteroatom substi­tute in the Cp ring bound to the metal.

Like LLDPE, HDPE made using single-site catalysts is targeted at the film mar­ket. Applications include blow-molded bags, agricultural films, and food packag­ing. Films made with HDPE are stronger and can be used for heavy-duty applica­tions; they can also be made thinner for comparable LLDPE uses. Some convert­ers, or polymer fabricators, blend these products with other polyethylenes to boost overall strength.

Fina uses its proprietary catalysts with licensed Phillips' slurry loop technology for HDPE production at its site in Ant­werp, Belgium. Dow also produces a high-

Traditional and single-site catalysts for polyolefins

Catalyst system

Heterogeneous titanium

Heterogeneous chromium

Homogeneous vanadium

Metallocenes

Constrained environment

Source: Montell

Activity

High

High

Low

High

Medium

Catalytic site

Multiple

Multiple

Single, multiple

Single

Single

Polyolefins made

Polyethylene, polypropylene

Polyethylene

Ethylene-propylene rubbers

Polyethylene, polypropylene

Polyethylene, polypropylene

Molecular weight range

Broad

Broad

Narrow, broad

Narrow

Narrow

JULY 6, 1998 C&EN 13

b u s i n e s s

density product the company suggests ™ could be used in pipe and other dura­ble applications.

The development of polypropyl­ene based on single-site catalysts is proceeding more slowly than that for polyethylene, and fewer companies are participating in this market. Tar-gor, the polypropylene joint venture between Hoechst and BASF (C&EN, May 12, 1997, page 18), began com­mercial production in Europe last fall. Exxon's polypropylene product, made in Baytown, Texas, was launched in 1995. Also, Fina has commercial poly­propylene production at its site in La-Porte, Texas, which is being expand­ed to allow for more metallocene poly­mer production.

Single-site catalysts have an addition­al level of molecular control with poly­propylene, owing to the stereochemis­try of the polymer. Specific isomers can be made—isotactic, with all of the methyl groups, on one side, or syndiotactic, with alternating methyl groups—depending on the performance required. Such control over the polymer structure can be very

Univation leads patent filings on single-site catalysts for polyethylene

Other3

47% Univation

Technology 18%

Hoechst 13%

Mitsui 6%

Dow Chemical Phillips BASF Montell 6 %

Petroleum ^% 4° /o

3%

Total cumulative patents = 1,500b

a Includes Fina (2%), Idemitsu (2%), Mitsubishi (2%), Mobil (2%), Tosoh (2%), BP Chemicals (1%), Shell (1%), and other smaller shares, b Patents filed worldwide as of Jan. 1, 1997, related to single-site catalysts for polyethylene. Source: Univation Technologies

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" Market observers suggest that sin­gle-site polypropylene with improved barrier properties and clarity could re­place polyethylene terephthalate in some bottle applications and polysty­rene in some packaging.

"Metallocene technology arrived too early for polypropylene," notes Catalyst Group's Murphy. Convention­al polypropylene continues to grow at almost twice the rate of polyethylene, which needed the technology to re­new its slowed growth. However, the leaders—Exxon along with BASF and Hoechst through Targor—can control their fates: "With the [corporate] align­ments in place and the technology well documented and protected, these leaders are certainly in the position to set the pace," says Murphy.

Following a few years of early de­velopment that served to prepare the market, these products are now poised to penetrate commodity mar­

kets as replacements in some existing polyolefin applications and in new appli­cations. Several analysts are bullish on their prospects and expect rapid growth in the next few years.

Catalyst Group forecasts annual de­mand for polyethylene made with all sin­gle-site catalysts at 26 billion lb in 2005, representing 15% of total polyethylene consumption. About 60% of these poly­mers will be made with metallocenes and the remainder by other single-site catalysts and noncatalytic advances in process technology. Single-site polypro­pylene is expected to penetrate the mar­ket by 5 to 6% by 2005, representing nearly 4 billion lb of annual demand.

Speaking at MetCon '98, Kenneth Sin­clair, principal at consulting firm STA Re­search, Sunnyvale, Calif., estimates the demand for polyethylene made from sin­gle-site catalysts at 3.2 billion lb in 2000 and 110 billion lb in 2015. Sinclair ac­knowledges that some of that volume will be "cannibalized" from conventional polyethylenes, but most will come from new polyethylene applications made possible by improved performance.

Townsend's Bahl shows similar opti­mism, predicting a demand of 4.2 billion lb in 2002. Most of the growth will occur in the U.S. because "the suppliers are here, the applications are usually devel­oped here, and converters in the U.S. are very familiar with the term metallocene. Everybody wants to be associated with it."

These estimates assume that produc­ers are able to overcome two critical is­sues that will have a significant impact

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on the market acceptance of these poly­mers: price and processibility.

After several years and millions of dol­lars of investment in R&D and market de­velopment efforts, many companies are eager to recover their costs. Price is an obvious tool to do this, but commodity markets seldom tolerate inflated prices.

"If the costs are so high to the cus­tomer that [use of the new polymer] doesn't result in an economic advan­tage," explains Equistar's Mack, "then you won't see a high growth rate in the metallocene area. The polymer needs to be positioned in a way that the customer can take advantage of the performance characteristics."

Also, a new entrant can help keep prices down in some markets. Bahl notes that LLDPE is a new market for Phillips, and, therefore, the company probably will price its material "reasonably" to penetrate the market.

Also, the actual costs for the catalysts are high right now. "One of the major costs associated with metallocene cata­lysts has been the catalyst cost itself," says Phillips' Brady. "As the volume grows and the technology improves, those costs will come down and be com­petitive with existing catalyst systems."

Custom catalyst manufacturer Albe­marle agrees. The company works under confidentiality agreements with several polymer producers that use single-site cat­alysts. "It is feasible to get the catalyst costs down—we can see that when the catalyst volumes become large enough," says A. T. Stoll, new-business manager for organometallics and catalysts. "That is not a hope for the distant future—but it is not too fer away."

Patrick G. Simms, Albemarle's business development manager, adds that the in­dustry seems to have moved beyond the catalyst cost issue. "At a recent conference in Germany, attendees said these costs are no longer in question; [lower costs] are happening as we speak."

Several analysts note that in recent months the initially high single-site poly­mer prices had been moving very close to what the market would bear. Howev­er, with polyolefin prices falling world­wide recently because of the Asian finan­cial crisis (C&EN, June 22, page 19), the gap between these products and conven­tional resins has widened again.

Processing problems have become a major issue for these polymers as they move into large, existing commodity markets. The industry infrastructure of converters is already in place, and most

Albemarle makes slngle-slte-catalyst precu

have invested heavily in equipment to handle existing polyolefins. Not surpris­ingly, narrow molecular weight poly­mers have very different melt and flow properties from polymers with a broad molecular weight distribution. Although the narrower range may provide some performance advantages, the processing of such polymers can be difficult.

"Customers are reluctant to embrace new materials," says Brady, "because it means they will have to learn how to process them and change the way they run their processing machines.

"The customers for polyethylene are large film companies," he continues. "They want to produce a lot of film and push the polyethylene through the ma­chines rapidly. They do not want to ad­just the machines or shut down a line because of [processing problems]."

In contrast, the emerging markets in Asia and South America may be more tol­erant of these processing differences, points out Bahl. Their newer processing equipment has greater flexibility and pumps with more power to move vis­cous materials.

Companies are using various technol­ogies to address the processing prob­lems. Dow, for example, emphasizes its ability to make LLDPE with long-chain branching with its Insite catalysts. The company says this branching "makes [its LLDPE] easier to process than other co­polymers having a narrow molecular weight distribution."

Borealis and Fina, for example, use two reactors to make bimodal polymers, which contain polymer chains with two different molecular weight distributions.

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The low molecular weight chains pro­vide some plasticizing of the longer chains and enhance the melt and flow characteristics of the polymers.

Another more subtle issue that catalyst and polymer producers are beginning to address is how to focus their product de­velopment efforts. With the new capabili­ty to make highly specialized products, ef­fective communication with customers is especially important to ensure that the new product meets the required perfor­mance targets.

"There is a great importance now on market focus," says Dow's Swogger, ad­mitting that this requirement surprised him. "The challenge is to match the tech­nical capability to the market need."

Joint ventures and alliances can help focus marketing efforts and provide spe­cific expertise. Through DuPont Dow Elastomers, Dow gained access to the elastomers market, where it previously had a small, fragmented presence.

"Dow developed the technology to make rubber, but had no application ex­pertise or market channel to the rubber industry," says Ashby L. Rice, vice presi­dent for technology at DuPont Dow Elas­tomers. "DuPont, on the other hand, had an ethylene-propylene-diene monomer business that was looking for a technolo­gy revitalization."

Exxon has a similar relationship with Dutch chemicals producer DSM, through a venture called Dex-Plastomers. The company sells polymers made with me-tallocenes to traditional elastomer mar­kets such as wire and cable, polymer modification, and foams.

Both of these ventures are targeting

JULY 6, 1998 C&EN 15

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business specialty markets where these products can be sold at higher prices and profit margins are generally better than com­modity markets. However, the volumes are much lower.

Equistar's Mack acknowledges that a small-volume market is not adequate. "In order to win in single-site catalysts, you will need to identify larger markets and move away from a specialty orientation to large-volume commodity-like markets."

He uses the term "commodity-like," not commodity, on purpose. The mar­kets for polymers made with single-site catalysts "are large-volume commodity­like markets—big, but with so much pos­sible differentiation, they are not really commodity markets."

Market size is certainly a key issue for these new catalysts and polymers, with so many large companies vying for posi­tion. However, in a commodity market, the presence of many players can be an advantage, particularly in the early devel­opment of a product.

"A lot of customers are resistant to buy from [only] one source of supply," says Univation's McPike. "They need a guarantee that more than one polymer producer will use [the technology]. That is starting to happen now."

One possible glitch in the apparently bright future for single-site catalysts is the current reduction in polymer de­mand due to the Asian economic crisis. But producers do not seem concerned, and some even see possible advantages.

"When you have a slowdown and re­actor capacity is idle," says Mack, "often researchers are given the green light to run in the commercial area. That acceler­ates commercialization."

Phillips' Brady adds that the delay of some Asian projects "is healthy for the poly­ethylene industry because we were headed for large overcapacity. Health in the indus­try provides money for companies to sup­port R&D and product development."

And healthy is how the single-site-cata­lyst technology looks now, ready to move into the mainstream markets and capture a lot of business. Major polyolefin producers have significant challenges because of the diversity of products possible with these catalysts—a big change after years of sell­ing large quantities of the same material— but many seem well prepared. And the opportunities are great.

"The advantage of single-site catalysts is that you don't have to make the same product," says Sinclair. "If you can do that, and your customers can appreciate that, you can both make a lot of money. "Λ

16 JULY 6, 1998 C&EN

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