Declaration in Support of Petitioners’ Reply
`
`
`UNITED STATES PATENT AND TRADEMARK OFFICE
`____________________
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`____________________
`
`E. I. DU PONT DE NEMOURS AND COMPANY and
`ARCHER-DANIELS-MIDLAND COMPANY,
`Petitioners,
`
`v.
`
`FURANIX TECHNOLOGIES B.V.,
`Patent Owner.
`
`____________________
`
`Case IPR2015-01838
`Patent 8,865,921
`____________________
`
`Declaration # 2 of Dr. Kevin J. Martin
`
`
`
`
`
`
`
`Petitioners' Exhibit 1028, Page 1 of 18
`
`
`
`
`UNITED STATES PATENT AND TRADEMARK OFFICE
`____________________
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`____________________
`
`E. I. DU PONT DE NEMOURS AND COMPANY and
`ARCHER-DANIELS-MIDLAND COMPANY,
`Petitioners,
`
`v.
`
`FURANIX TECHNOLOGIES B.V.,
`Patent Owner.
`
`____________________
`
`Case IPR2015-01838
`Patent 8,865,921
`____________________
`
`Declaration # 2 of Dr. Kevin J. Martin
`
`
`
`
`
`
`
`Petitioners' Exhibit 1028, Page 1 of 18
`
`
`
`
`
`I, Kevin J. Martin, do hereby declare as follows:
`
`I have been asked to submit an opinion in support of a Reply Brief
`
`regarding the subject matter of the claims of U.S. Patent No. 8,865,921 (“the ’921
`
`patent”) (Exhibit 1001) in response to Patent Owner’s Response (Paper No. 23)
`
`(“the Response”), including the testimony of Dr. Schammel.
`
`I describe herein portions of Dr. Schammel’s testimony (Exh. 2020) and
`
`the Response with which I do not agree. Other portions of Dr. Schammel’s
`
`testimony and the Response are not addressed; however, just because I do not
`
`discuss a portion of the testimony or reply, does not imply or suggest that I agree
`
`with Patent Owner’s or Dr. Schammel’s representations.
`
`As I previously testified (e.g., Exhibit 1009), I am very familiar with the
`
`subject matter of the claims of the ’921 patent, and worked in the relevant field for
`
`a number of years. A further description of my qualifications can be found in my
`
`CV. See Exhibit 1015.
`
`Similar to my prior Declaration, I am not being compensated beyond my
`
`current salary for my time preparing this declaration and any time associated with
`
`any subsequent deposition. I am, however, being reimbursed for reasonable and
`
`customary expenses associated with my work and testimony. I do not expect to
`
`1
`
`
`
`Petitioners' Exhibit 1028, Page 2 of 18
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`
`
`
`
`receive any compensation contingent on the outcome of this matter or the specifics
`
`of my testimony.
`
`I.
`
`A PERSON OF ORDINARY SKILL IN THE ART
`I have reviewed Dr. Schammel’s declaration and supporting testimony
`
`and understand that he does not agree with my description of a person of ordinary
`
`skill in the art. See Exh. 2003 ¶ 44. Instead, Dr. Schammel asserts “a person of
`
`ordinary skill in the art in 2009 would have been a person having at least a
`
`bachelor’s degree in chemistry or chemical engineering, having worked in the field
`
`of chemical process development for at least five years [or] having experience in
`
`the preparation of furan compounds from biomass and in the catalysis of oxidation
`
`of furan compounds.” Id.; see also Exh. 2020 at 18:6-14.
`
`According to Dr. Schammel, a person having ordinary skill in the art
`
`would have been able to run oxidation reactions to arrive at FDCA, would have
`
`been able to run tests within a particular range if provided, and would be capable
`
`of reviewing and understanding peer-reviewed publications. See Exh. 2020 at
`
`20:5-8 and 20:19-21:6. Dr. Schammel further testified that a person having
`
`ordinary skill in the art would have been capable of designing experiments. See id.
`
`at 20:15-18.
`
`
`
`2
`
`
`
`Petitioners' Exhibit 1028, Page 3 of 18
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`
`
`
`
`While I agree with Dr. Schammel’s description of the capabilities of his
`
`described person of ordinary skill in the art, I disagree with the limitations placed
`
`on that person, especially in view of his deposition testimony wherein he admitted
`
`that a person of ordinary skill in the art would not have been able to necessarily
`
`fully practice the invention. See Exh. 2020 78:11-14. In my opinion, the
`
`difference between my description of a person of ordinary skill in the art and Dr.
`
`Schammel’s description is that the added experience and/or education my
`
`description requires would have allowed that person to draw further inferences
`
`from peer-reviewed publications based on the additional experience and/or
`
`education, and that a person of ordinary skill in the art would have had a
`
`reasonable expectation of successfully optimizing conditions for oxidation
`
`reactions based, in part, on peer-reviewed publications. My description of a person
`
`having ordinary skill in the art would have been able to obtain workable ranges for
`
`the catalytic oxidation of HMF to FDCA, and to design experiments to vary
`
`variables and determine an optimal range to maximize yields. This is supported by
`
`the references themselves that provide ranges for temperatures, pressures, reaction
`
`times, and catalyst concentrations, as well as inferences drawn from the
`
`experiments reported. See, e.g., the ’732//7:5-7 (“preferred time of the reaction is
`
`determined by the temperature, pressure and catalyst concentration such that a
`
`maximum yield of diacid is obtained.”); id. at 15:9-11 (the data “also illustrates
`
`
`
`3
`
`
`
`Petitioners' Exhibit 1028, Page 4 of 18
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`
`
`
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`that increasing catalyst concentrations at a given temperature and time, nearly
`
`always increased the FDA yield.”); Partenheimer//105 (“yield increases with
`
`catalyst concentration (Figure 7) [and] with temperature (entries 1 and 2 and 3 and
`
`4 of Table 3).”); id. (discussing data showing staged reactions achieving no greater
`
`yield than non-staged reactions); id. (“[i]t is believed that variation of the molar
`
`amounts of the Co, Mn, Zr, and Br could well improve the yield of 2,5-
`
`furandicarboxylic acid.”); ’318 at [0007] (disclosing reactor temperatures of from
`
`about 50° C to about 200° C.); id. at Figs. 30, 31 (disclosing the conversion of
`
`HMF to FDCA at 160°C and at either 150 psi of air (oxygen partial pressure of
`
`2.17 bar) or 300 psi (oxygen partial pressure of 4.34 bar)), below:
`
`
`
`4
`
`
`
`
`
`Petitioners' Exhibit 1028, Page 5 of 18
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`
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`
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`“FIG. 30 shows HMF conversion and product selectivity as a function of time
`
`on stream utilizing the catalyst of FIG. 28 at varied temperature. P=150 psig
`
`air, T=140-160° C., 0.5% HMF LHSV=7.5 h-1, GHSV=300 h-1.” ’318//[0038]
`
`“FIG. 31 shows HMF conversion and product selectivity as a function of time
`
`on stream utilizing the catalyst of FIG. 28 at varied LHSV at varied
`
`temperature and at varied psi air. P=150-300 psig air, T=100-160° C., 0.5%
`
`HMF LHSV=7.5-15 h-1, GHSV=300 h-1.” ’318//[0039].
`
`
`
`
`
`
`
`5
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`
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`
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`Petitioners' Exhibit 1028, Page 6 of 18
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`
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`
`
`II. THE ’732 PUBLICATION AND PARTENHEIMER
`A. MOTIVATION TO COMBINE
`8. I previously reviewed and provided my opinions relating to
`
`International Publication No. WO 01/072732 (“the ’732 publication”) (Ex.
`
`1002). See, e.g., Ex. 1009 ¶¶ 16, 63-64.
`
`9. In my review of the Response, with respect to the ’732 publication,
`
`the Response appears to focus solely on a number of the Examples put forth in
`
`the ’732 publication. In particular, the Response discusses Examples 38-40 of
`
`the ’732 publication. See Paper 23 at 6, 15-17.
`
`10. The ’732 publication describes Examples 16-40 as a catalytic
`
`oxidation of HMF with acetic acid in the presence of air at 1000 psi. See Ex.
`
`1002, p. 15, ll. 3-4. Furthermore, as demonstrated in Table 4 of the ’732
`
`publication, the different examples were operated at, among other things,
`
`different temperatures, different catalyst concentrations, and different reaction
`
`times.
`
`11. The ’732 publication explicitly compares Examples 35-37 with
`
`Examples 38-40. See Ex. 1002, p. 15, ll. 12-14. I have reproduced the relevant
`
`portion of Table 4 below for ease of consideration.
`
`
`
`6
`
`
`
`Petitioners' Exhibit 1028, Page 7 of 18
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`
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`
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`
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`
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`
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`Examples 35-37 were each conducted at a temperature of 105 °C. See
`
`Ex. 1002, Table 4. In comparison, Examples 38-40 were conducted with “staged”
`
`temperatures of 75 °C for 2 hours and 150 °C. See id. at p. 15, ll. 12-14. The ’732
`
`publication appear to have concluded that “staging of the temperature gave higher
`
`yields.” Id. at p. 15, ll. 14-15.
`
`With additional experiments, however, at least two of the co-inventors
`
`found that the conclusion was not exactly correct. While the ’732 publication
`
`states “[t]he staging of the temperature gave higher yields” (Ex. 1002, p. 15, ll. 14-
`
`15), one skilled in the art would not have reached that conclusion because
`
`Partenheimer (Ex. 1003), a peer-reviewed publication authored by two of the co-
`
`
`
`7
`
`
`
`Petitioners' Exhibit 1028, Page 8 of 18
`
`
`
`
`
`inventors of the ’732 publication1 later in time,2 states “staging the temperature
`
`from an initial value … for 1 [hour] and then [at a higher temperature] for 2 [hour]
`
`gave no better [yields] than the oxygenation [at the higher temperature] for 3
`
`[hour] (Figure 7).” See Ex. 1003, p. 105. Thus, one skilled in the art would have
`
`understood from the later teachings of Partenheimer that his previous conclusion
`
`was incorrect and instead staging a reaction is no more beneficial than only
`
`operating the reaction at the higher temperature, at least with respect to yields.
`
`Furthermore, I have reviewed both the ’732 publication and
`
`Partenheimer and understand the references to have some overlap. For example,
`
`some of Examples 16-40 of the ’732 publication are included in Tables 2 and 3 of
`
`Partenheimer. As I previously testified, and as proffered in the Response and by
`
`
`1 Compare the ’732 publication listing, among others, Walt Partenheimer and
`
`Vladimir V. Grushin with Partenheimer listing Walt Partenheimer and Vladimir V.
`
`Grushin as co-authors. See also the ’732 publication (listing E. I. du Pont de
`
`Nemours and Company as applicant) and Partenheimer (listing the address as
`
`“Central Research and Development, E. I. DuPont de Nemours & Co.”).
`
`2 Compare the ’732 publication’s earliest effective filing date (March 27, 2000)
`
`with Partenheimer having a “[r]eceived” date of August 3, 2000.
`
`
`
`8
`
`
`
`Petitioners' Exhibit 1028, Page 9 of 18
`
`
`
`
`
`Dr. Schammel, both of these references are related and include some of the same
`
`disclosure.
`
`As I stated above, one of ordinary skill in the art would understand the
`
`’732 publication to have reached its conclusions, as of the priority date of the
`
`document, on March 27, 2000. See supra. A person of ordinary skill in the art
`
`would understand Partenheimer, with a receiving date of August 3, 2000, to be a
`
`later filed document than the ’732 publication.
`
`Therefore, in my opinion, a person having ordinary skill in the art
`
`reviewing both the ’732 publication and Partenheimer, would understand that the
`
`conclusions arrived at in Partenheimer were at a later date than the conclusions
`
`arrived at in the ’732 publication, and hence whenever the conclusions conflict,
`
`Partenheimer would have been the more authoritative and final conclusion.
`
`Moreover, from the later disclosure of Partenheimer, one of ordinary
`
`skill in the art would not have considered that staging the temperature would have
`
`resulted in higher yields, and instead would have been motivated to simply react
`
`HMF at a higher contact temperature to obtain FDCA as explained in
`
`Partenheimer. In my opinion, additional factors would further motivate one skilled
`
`in the art to utilize a single higher temperature, for example, simplification of the
`
`
`
`9
`
`
`
`Petitioners' Exhibit 1028, Page 10 of 18
`
`
`
`
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`process, reduction in process control requirements, improved repeatability of the
`
`process, etc.
`
`B. YIELD
`Partenheimer states that “[e]xtrapolation…suggests that the maximum
`
`obtainable 2,5-furandicarboxylic acid yield is about 70% using the Co/Mn/Zr/Br
`
`catalyst at the specified molar ratios of these elements.” Ex. 1003 at 105. In my
`
`opinion, by Partenheimer using the word “suggests,” one skilled in the art would
`
`understand that greater yields of FDCA could be achieved and would hence not be
`
`unexpected. Indeed, Partenheimer demonstrates, in my opinion, utilizing Figure 7,
`
`that as catalyst concentration increases, yield of FDCA increases. See
`
`Partenheimer//Figure 7. Thus, in my opinion, it would have been obvious to one of
`
`ordinary skill in the art, at least from the representations of Figure 7 of
`
`Partenheimer, that increasing catalyst concentration could increase yield even
`
`greater than 70%. See id.; see also ’732//15:9-11 (“It also illustrates that
`
`increasing catalyst concentrations at a given temperature and time, nearly always
`
`increased FD[C]A yield.”).
`
`I have reproduced Figure 7 of Partenheimer below for ease of
`
`consideration.
`
`
`
`10
`
`
`
`Petitioners' Exhibit 1028, Page 11 of 18
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`
`
`
`
`
`
`III. THE ’318 PUBLICATION
`I address U.S. Patent Publication No. 2008/0103318 (“the ’318
`
`publication” or “’318”) (Exh. 1008) because it was addressed by the Decision to
`
`Institute IPR, by Patent Owner in its Response and by Dr. Schammel.
`
`I have reviewed, analyzed, and understand the specification and claims
`
`of the ’318 publication, and hereby discuss its disclosure as one of ordinary skill in
`
`the art would have understood it.
`
`
`
`11
`
`
`
`Petitioners' Exhibit 1028, Page 12 of 18
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`
`
`
`
`The ’318 publication describes a process including the catalytic
`
`oxidation of HMF to FDCA. The oxidation of HMF is in the presence of acetic
`
`acid and a noble metal Pt/ZrO2 catalyst. The preferred temperature range for the
`
`oxidation is “from 100°C through about 160°C,” and a pressure “of 150-500 psi.”
`
`’318//[0050]; see also Figures 30, 31, and 39 (showing HMF conversion to FDCA
`
`at temperatures of 100° C through 160° C and pressures of 150 psi to 300 psi).
`
`More broadly, the ’318 publication discloses a reactor temperature range
`
`of from 50 °C to 200 °C for the oxidation. ’318, Abstract. A range that, in my
`
`opinion, overlaps the claimed temperature ranges of the ’921 patent.
`
`I have reviewed the Petition’s representations regarding the disclosure
`
`of the ’318 publication, and to the best of my understanding, the Petition accurately
`
`represents the disclosure of the ’318 publication, and why one skilled in the art
`
`would combine the teachings of the ’318 publication with the ’732 publication and
`
`RU ’177.
`
`The ’318 publication is directed to the same field of endeavor as the
`
`’732 publication, the liquid-phase catalytic oxidation in acetic acid of HMF to
`
`produce FDCA. See ’318//[0049]-[0054]. Similar to the ’732 publication, the ’318
`
`publication teaches temperature ranges above 100 °C, and even above 150 °C.
`
`Similar to the ’732 publication, the ’318 publication provides data to suggest to
`
`
`
`12
`
`
`
`Petitioners' Exhibit 1028, Page 13 of 18
`
`
`
`
`
`one of ordinary skill in the art that higher temperatures can increase yield. For
`
`example, Figure 31 of the ’318 publication shows FDCA yields of about 40-50%
`
`in oxidizing HMF at 100° C; those yields are increased to about 80% when the
`
`reaction is conducted at a temperature of 160° C.
`
`In my opinion, the ’318 publication teaches one of ordinary skill in the
`
`art that pressures from 150-500 psi can be utilized to successfully react HMF into
`
`FDCA. See id. at [0050]. This range translates to an oxygen partial pressure of
`
`2.17 to 7.24 bar when air is used, or alternatively, an oxygen partial pressure of
`
`10.34 to 34.47 bar when pure oxygen is used.3
`
`Thus, in my opinion, one skilled in the art would look to combine the
`
`teachings of the ’732 publication and the ’318 publication because both are
`
`directed to converting HMF to FDCA, both recite overlapping temperatures for the
`
`reaction, and both use a catalytic oxidation in a liquid solvent of acetic acid-water
`
`mixture. See, e.g., id. In addition, both references refer to reactions done in batch
`
`reactions.
`
`
`3 This is calculated by converting psi to bar (1 psi = 0.067 bar) and, in the case of
`
`air, further multiplying the bar value by 0.21, which is essentially the percentage of
`
`oxygen in air.
`
`
`
`13
`
`
`
`Petitioners' Exhibit 1028, Page 14 of 18
`
`
`
`
`
`The ’318 publication explicitly teaches one skilled in the art that a
`
`temperature range “from 100°C through about 160°C,” is a viable temperature for
`
`the catalytic conversion of HMF to FDCA, thus in my opinion, further confirming
`
`the disclosed range of 50 °C to 250 °C taught by the ’732 publication. Moreover,
`
`in my opinion, even though the ’318 publication relies upon a different catalyst
`
`system than the ’732 publication, one skilled in the art would understand the ’318
`
`publication as confirming the viability of the higher temperature range disclosed in
`
`the ’732 publication.
`
`IV. COMMERCIAL VIABILITY
`29. As I previously testified, I have reviewed the ’921 patent and each
`
`example provided is conducted at a scale of about 5 mL in 8 mL reaction
`
`vessels. In addition, I have reviewed Dr. Schammel’s and Dr. Gruter’s
`
`declarations, and the recently conducted experiments—purportedly showing
`
`unexpectedly high yields commensurate in scope of the claims—were also
`
`conducted at a scale of about 5 mL in 8 mL reaction vessels.
`
`30. In my opinion, and as one skilled in the art would understand,
`
`production of FDCA in these types of small lab scale reactors is not
`
`commercially viable because it is not at a sufficient commercial scale. As
`
`identified by Patent Owner’s expert Dr. Gruter, the FDCA monomer is
`
`intended to create a wide range of polymers “such as polyesters, polyamids and
`
`
`
`14
`
`
`
`Petitioners' Exhibit 1028, Page 15 of 18
`
`
`
`
`
`polyurethanes, as well as coating resins, plasticizers and other chemical
`
`products.” Ex. 2007 ¶ 17. Indeed, in my opinion, if a monomer (FDCA) is
`
`intended to create these types of polymers, which are commonly understood to
`
`be widely used in vast quantities, a significant quantity of such monomer
`
`would be required to be produced in each batch, certainly in at least the
`
`hundreds or thousands of liters, if not more.
`
`31. Instead, the ’921 publication reports conversions from 0.5 ml of
`
`starting material stock solution in acetic acid (0.78 mmol/ml), which converts
`
`to approximately 0.39 mmoles HMF. Thus, even if 78.08 % yield is achieved,
`
`the greatest disclosed in the ’921 publication, an insignificant amount of FDCA
`
`is produced. Even producing the reaction in reactor blocks containing 12 batch
`
`reactors (Ex. 1001, col. 6, ll. 8-10), an insignificant amount of the polymer is
`
`produced.
`
`32. In fact, Patent Owner’s expert Dr. Schammel agrees that the reactor
`
`sizing disclosed in the ’921 publication and subsequent testing by Dr. Gruter is
`
`insufficient to be at the commercial scale, and instead would need to produce
`
`FDCA at “much higher levels” including “pilot plants and so forth.” See Ex.
`
`77:22-78:22. In my opinion, based on my understanding of the need for
`
`FDCA, pilot plants would only be the start of the scale of this process to meet
`
`
`
`15
`
`
`
`Petitioners' Exhibit 1028, Page 16 of 18
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`
`
`
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`commercial needs and thus be commercially viable. Once a pilot plant is
`
`established and successfully run, it is common, as would be understood by a
`
`person having ordinary skill in the art, that a full size plant would be built and
`
`established, likely orders of magnitude greater than the reactors disclosed in
`
`the ’921 publication. Thus, as even admitted by Patent Owner’s expert, the
`
`’921 patent fails to disclose production at a commercial scale, and thus fails to
`
`teach to one of ordinary skill in the art, a commercially viable process. See id;
`
`see also Exh. 2020 at 78:11-18 (“Q[:] In your opinion, a person of ordinary
`
`skill in the art as you define it, would they know how to scale up from eight
`
`milliliters? A Not necessarily…I’m an expert and I wouldn’t rely on it. You
`
`need teams of engineers and so forth to eventually do that…”).
`
`V. DR. GRUTER’S 2016 EXPERIMENTS
`I have reviewed and analyzed Dr. Gruter’s declaration (Exh. 2007) and
`
`the supporting exhibits.
`
`Dr. Gruter’s declaration discussed experiments conducted in 2016
`
`reproducing Example 1 and Table 1 of the ’921 patent and also conducting
`
`additional experiments at additional temperatures from the range between 140 °C
`
`and 200 °C. See Ex. 2007 ¶ 31. In my opinion, and from my review of Dr.
`
`Gruter’s declaration, the experiments appear to be conducted at essentially the
`
`same scale as the experiments disclosed in the ’921 patent. See id. at ¶¶ 32-33. For
`
`
`
`16
`
`
`
`Petitioners' Exhibit 1028, Page 17 of 18
`
`
`
`Gruter’s declaration, the experiments appear to be conducted at essentially the
`
`same scale as the experiments disclosed in the ’92l patent. See id. at 111] 32-33. For
`
`example, the reactors were similarly loaded with 0.5 ml of substrate solution and
`
`conducted in 8 ml reaction vessels. See id.
`
`35. From the information disclosed in Dr. Gruter’s declaration I calculated
`
`the catalyst concentration utilized by Dr. Gruter’s 2016 experiments. The 2016
`
`experiments utilized substantially the same catalyst concentration as used in the
`
`Examples of the ’92l patent.
`
`I further declare that all statements made herein of my own knowledge are
`
`true and that all statements made on information and belief are believed to be true;
`
`and further that these statements were made with the knowledge that willful false
`
`statements and the like so made are punishable by fine or imprisonment, or both,
`
`under Section 1001 of Title 18 of the United States Code.
`
`
`
`
`
`
`
`Kevin J. Martin
`
`Date:
`
`C/( /K;/Z0/(5
`
`200365.000] 5/lO3445454v.l
`
`17
`
`Petitioners‘ Exhibit 1028, Page 18 of 18
`
`Petitioners' Exhibit 1028, Page 18 of 18
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