Filed: May 1, 2019
`
`
`
`Filed on Behalf of:
`Patent Owner LiquidPower Specialty Products Inc.
`By:
`Douglas W. McClellan, Reg. No. 41,183
`Weil, Gotshal & Manges LLP
`700 Louisiana, Suite 1700
`Houston, Texas 77002
`Tel: (713) 546-5000, Fax: (713) 224-9511
`doug.mcclellan@weil.com
`
`Elizabeth S. Weiswasser, Reg. No. 55,721
`Weil, Gotshal & Manges LLP
`767 Fifth Avenue New York, NY 10153
`Tel: (212) 310-8000, Fax: (212) 310-8007
`elizabeth.weiswasser@weil.com
`
`
`
`
`UNITED STATES PATENT AND TRADEMARK OFFICE
`______________________
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`______________________
`BAKER HUGHES INCORPORATED, a GE COMPANY LLC
`Petitioner
`v.
`LIQUIDPOWER SPECIALTY PRODUCTS INC.,
`Patent Owner
`______________________
`Case IPR2016-01901
`Patent No. 8,450,249 B2
`PATENT OWNER’S NOTICE OF APPEAL
`
`
`
`
`
`
`
`Filed on Behalf of:
`Patent Owner LiquidPower Specialty Products Inc.
`By:
`Douglas W. McClellan, Reg. No. 41,183
`Weil, Gotshal & Manges LLP
`700 Louisiana, Suite 1700
`Houston, Texas 77002
`Tel: (713) 546-5000, Fax: (713) 224-9511
`doug.mcclellan@weil.com
`
`Elizabeth S. Weiswasser, Reg. No. 55,721
`Weil, Gotshal & Manges LLP
`767 Fifth Avenue New York, NY 10153
`Tel: (212) 310-8000, Fax: (212) 310-8007
`elizabeth.weiswasser@weil.com
`
`
`
`
`UNITED STATES PATENT AND TRADEMARK OFFICE
`______________________
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`______________________
`BAKER HUGHES INCORPORATED, a GE COMPANY LLC
`Petitioner
`v.
`LIQUIDPOWER SPECIALTY PRODUCTS INC.,
`Patent Owner
`______________________
`Case IPR2016-01901
`Patent No. 8,450,249 B2
`PATENT OWNER’S NOTICE OF APPEAL
`
`
`
`
`
`IPR2016-01901
`U.S. PATENT 8,450,249
`
`INTRODUCTION
`LiquidPower Specialty Products Inc.’s (“LSPI’s”) appeal stems from the
`
`Patent Trial and Appeal Board’s Final Written Decision entered on April 4, 2018
`
`(Paper 65) (the “Final Written Decision”) in the above-captioned inter partes
`
`review of United States Patent No. 8,450,249 (the “’249 Patent”). Please note that
`
`the Final Written Decision in this matter has been sealed to the public, and
`
`currently only the Parties and the Board have access to it. The redacted version of
`
`the Final Written Decision is attached to this Notice. This notice is timely filed
`
`within 63 days of the Board’s Decision to Deny Patent Owner’s Request for
`
`Rehearing (Paper 70), which was entered on March 4, 2019. 37 C.F.R. §
`
`90.3(b)(1).
`
`LSPI’S APPEAL
`Please take notice that under 35 U.S.C. §§ 141(c), 142, 319; 37 C.F.R.
`
`§§90.2(a), 90.3(a), and Federal Rules of Appellate Procedure/Federal Circuit Rule
`
`4(3)(a), Patent Owner LSPI hereby appeals to the United States Court of Appeals
`
`for the Federal Circuit from the Final Written Decision based on the “Decision,
`
`Institution of Inter Partes Review” entered on April 07, 2017 (Paper 10) (the
`
`“Institution Decision”).
`
`LSPI’S ISSUES ON APPEAL
`In accordance with 37 C.F.R. § 90.2(a)(3)(ii), LPSI’s issues on appeal may
`
`include, but are not limited to: (i) the Board’s finding that claims 1-5 of the ’249
`
`2
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`
`
`IPR2016-01901
`U.S. PATENT 8,450,249
`
`patent are unpatentable under 35 U.S.C. § 103 as obvious over the combination of
`
`the Holtmyer Publication, the Holtmyer Patent, and Carnahan; (ii) the Board’s
`
`finding that claims 1-5 of the ’249 patent are unpatentable under 35 U.S.C. § 103
`
`as obvious over the combination of Inaoka and Carnahan; (iii) whether the
`
`objective evidence of non-obviousness precludes each of the findings of
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`obviousness on claims 1-5 of the ’249 patent; (iv) the Board’s claim construction;
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`and (v) any findings or determinations supporting or related to the aforementioned
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`issues, as well as all other issues decided adversely to LSPI in any orders,
`
`decisions, rulings, and/or opinions.
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`Simultaneously with this submission, LSPI is filing a true and correct copy
`
`of this Notice of Appeal with the Director of the United States Patent and
`
`Trademark Office and a true and correct copy of the same, along with the required
`
`docketing fee, with the Clerk of the United States Court of Appeals for the Federal
`
`Circuit as set forth in the accompanying Certificate of Filing.
`
`3
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`
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`Dated: May 1, 2019
`
`IPR2016-01901
`U.S. PATENT 8,450,249
`
`Respectfully Submitted,
`
`
`
`/Elizabeth S. Weiswasser/
`Douglas W. McClellan, Reg. No. 41,183
`Melissa L. Hotze, Reg. No. 55,279
`Weil, Gotshal & Manges LLP
`700 Louisiana, Suite 1700
`Houston, TX 77002
`Tel: (713) 546-5000
`Fax: (713) 224-9511
`doug.mcclellan@weil.com
`melissa.hotze@weil.com
`
`Elizabeth S. Weiswasser, Reg. No. 55,721
`Weil, Gotshal & Manges LLP
`767 Fifth Avenue
`New York, NY 10153
`Tel: (212) 310-8000
`Fax: (212) 310-8007
`elizabeth.weiswasser@weil.com
`
`
`Attorneys for Patent Owner LiquidPower
`Specialty Products Inc.
`
`4
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`IPR2016-01901
`U.S. PATENT 8,450,249
`
`CERTIFICATE OF FILING
`The undersigned hereby certifies that, in addition to being electronically
`
`filed through PTAB E2E, a true and correct copy of the above-captioned PATENT
`
`OWNER’S NOTICE OF APPEAL is being sent via priority mail on May 1, 2019,
`
`to the Director of the United States Patent and Trademark Office, at the following
`
`address:
`
`Director of the United States Patent and Trademark Office
`c/o Office of the General Counsel, 10B20
`Madison Building East
`600 Dulany Street
`Alexandria, VA 22314
`The undersigned also hereby certifies that a true and correct copy of the
`
`above-captioned PATENT OWNER’S NOTICE OF APPEAL and the filing fee is
`
`being filed via CM/ECF with the Clerk’s Office of the United States Court of
`
`Appeals for the Federal Circuit on May 1, 2019.
`
`Dated: May 1, 2019
`
`
`
`
`
`Respectfully Submitted,
`
`/Elizabeth S. Weiswasser/
`Elizabeth S. Weiswasser
`Reg. No. 55,721
`
`
`
`
`
`5
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`IPR2016-01901
`U.S. PATENT 8,450,249
`
`CERTIFICATE OF SERVICE
`I hereby certify that on May 1, 2019, a copy of PATENT OWNER’S
`
`NOTICE OF APPEAL was served by filing this document through the PTAB’s
`
`E2E Processing System as well as delivering a copy via electronic mail upon the
`
`following:
`
`Herbert D. Hart III
`Registration No. 30,063
`McAndrews, Held & Malloy, Ltd.
`500 West Madison Street
`Chicago, Illinois 60661
`Tel.: (312) 775-8000
`Email: hhart@mcandrews-ip.com
`George F. Wheeler
`Registration No. 28,766
`McAndrews, Held & Malloy, Ltd.
`500 West Madison Street
`Chicago, Illinois 60661
`Tel.: (312) 775-8000
`Email: gwheeler@mcandrews-ip.com
`Aaron F. Barkoff
`Registration No. 52,591
`McAndrews, Held & Malloy, Ltd.
`500 West Madison Street
`Chicago, Illinois 60661
`Tel.: (312) 775-8000
`Email: abarkoff@mcandrews-ip.com
`Peter J. Lish
`Registration No. 59,383
`McAndrews, Held & Malloy, Ltd.
`500 West Madison Street
`Chicago, Illinois 60661
`Tel.: (312) 775-8000
`Email: plish@mcandrews-ip.com
`
`6
`
`
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`IPR2016-01901
`U.S. PATENT 8,450,249
`
`Dated: May 1, 2019
`
`
`
`Respectfully Submitted,
`
`/Elizabeth S. Weiswasser/
`Elizabeth S. Weiswasser
`Reg. No. 55,721
`
`
`
`
`
`7
`
`
`
`Trials@uspto.gov
`571-272-7822
`
`Paper No. 71
`Entered: March 8, 2019
`PUBLIC VERSION WITH REDACTIONS
`
`UNITED STATES PATENT AND TRADEMARK OFFICE
`____________
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`____________
`
`BAKER HUGHES, a GE COMPANY, LLC
`(f/k/a BAKER HUGHES INCORPORATED),1
`Petitioner,
`
`v.
`
`LIQUIDPOWER SPECIALTY PRODUCTS INC.
`(f/k/a/ LUBRIZOL SPECIALTY PRODUCTS, INC.),
`Patent Owner.
`____________
`
`Case IPR2016-01901
`Patent 8,450,249 B2
`____________
`Before KRISTINA M. KALAN, CHRISTOPHER M. KAISER, and
`MICHELLE N. ANKENBRAND, Administrative Patent Judges.
`
`KALAN, Administrative Patent Judge.
`
`FINAL WRITTEN DECISION
`Holding Claims 1–5 Unpatentable
`35 U.S.C. § 318(a); 37 C.F.R. § 42.73
`Dismissing Patent Owner’s Motion to Exclude
`37 C.F.R. § 42.64(c)
`Denying Without Prejudice Petitioner’s and Patent Owner’s Motions to Seal
`37 C.F.R. § 42.54
`
`1 Petitioner represents that its name has changed from Baker Hughes
`Incorporated to Baker Hughes, a GE Company, LLC. Paper 20, 2.
`Accordingly, we modify the case caption to reflect that change.
`
`
`
`IPR2016-01901
`Patent 8,450,249 B2
`
`INTRODUCTION
`I.
`Baker Hughes, a GE Company, LLC (f/k/a Baker Hughes
`Incorporated) (“Petitioner”) requested an inter partes review of claims 1–5
`of U.S. Patent No. 8,450,249 B2 (“the ’249 patent,” Ex. 1003). Paper 2
`(“Pet.”). LiquidPower Specialty Products Inc. (f/k/a/ Lubrizol Specialty
`Products, Inc.) (“Patent Owner”) filed a Preliminary Response. Paper 9
`(“Prelim. Resp.”). We instituted an inter partes review of claims 1–5 on
`certain grounds of unpatentability alleged in the Petition. Paper 10 (“Dec.”).
`After institution of trial, Patent Owner filed a Patent Owner Response.
`Paper 19 (“PO Resp.” (public version)). Petitioner filed a Reply. Paper 31
`(“Reply” (public version)). Patent Owner, with Board authorization, filed a
`Sur-Reply. Paper 40 (“Sur-Reply” (public version)). An oral hearing was
`held on December 4, 2017. A transcript of the hearing is included in the
`record. Paper 63 (“Tr.” (public version)).
`We have jurisdiction under 35 U.S.C. § 6. This Final Written
`Decision is issued pursuant to 35 U.S.C. § 318(a) and 37 C.F.R. § 42.73.
`For the reasons that follow, we determine that Petitioner has established by a
`preponderance of the evidence that claims 1–5 of the ’249 patent are
`unpatentable.
`A. Related Proceedings
`Petitioner identifies the following pending litigation involving
`the ’249 patent: Lubrizol Specialty Products, Inc. v. Baker Hughes Inc.,
`No. 4:15-cv-02915 (S.D. Tex.). Pet. 2; Paper 20, 3. Petitioner also
`identifies U.S. Patent Application No. 13/209,119, filed on August 12, 2011,
`as pending, and represents that the ’119 application claims benefit to, and is
`a continuation in part of, U.S. Patent Application No. 11/615,539 (now U.S.
`
`2
`
`
`
`IPR2016-01901
`Patent 8,450,249 B2
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`Patent No. 8,022,118, “the ’118 patent”) to which the ’249 patent claims
`priority. Pet. 3.
`Petitioner identifies two additional instituted inter partes review
`proceedings involving Petitioner’s challenges to patents related to the ’249
`patent: IPR2016-01903 (challenging U.S. Patent No. 8,426,498 B2), and
`IPR2016-01905 (challenging U.S. Patent No. 8,450,250 B2). See Pet. 2;
`Paper 8, 3. Petitioner also filed an earlier Petition requesting an inter partes
`review of the ’118 patent. Baker Hughes Inc. v. Lubrizol Specialty Prods.,
`Inc., Case IPR2016-00734 (“734 IPR”), Paper 2. We issued a final written
`decision in the 734 IPR on October 1, 2017. 734 IPR, Paper 79; Paper 85
`(public version).
`B. The ’249 Patent
`The ’249 patent, titled “Drag Reduction of Asphaltenic Crude Oils,”
`issued on May 28, 2013. Ex. 1003, at [54], [45]. The ’249 patent relates to
`a “method of introducing a drag reducing polymer into a pipeline such that
`the friction loss associated with the turbulent flow though [sic] the pipeline
`is reduced by suppressing the growth of turbulent eddies,” in which the
`“drag reducing polymer is introduced into a liquid hydrocarbon having an
`asphaltene content of at least 3 weight percent and an API gravity of less
`than about 26° to thereby produce a treated liquid hydrocarbon.” Id. at [57].
`According to the specification, “[w]hen fluids are transported by a
`pipeline, there is typically a drop in fluid pressure due to the friction
`between the wall of the pipeline and the fluid.” Id. at 1:20–22. The pressure
`drop increases with increasing flow rate, resulting in energy losses and
`inefficiencies that increase equipment and operation costs. Id. at 1:24–32.
`
`3
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`IPR2016-01901
`Patent 8,450,249 B2
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`The problems associated with pressure drop are most acute when fluids are
`transported over long distances. Id. at 1:29–31.
`Before the ’249 patent, it was known to use drag reducing polymers in
`the fluid flowing through a pipeline to alleviate the problems resulting from
`pressure drop. Id. at 1:33–35. A drag reducing polymer “is a composition
`capable of substantially reducing friction loss associated with the turbulent
`flow of a fluid through a pipeline,” and such a composition works by
`“suppress[ing] the growth of turbulent eddies, which results in higher flow
`rate at a constant pumping pressure.” Id. at 1:37–42. Drag reduction
`generally “depends in part upon the molecular weight of the polymer
`additive and its ability to dissolve in the hydrocarbon under turbulent flow.”
`Id. at 1:44–46.
`According to the specification, because conventional drag reducing
`polymers do not perform well in crude oils having a low API gravity2 and/or
`a high asphaltene content, there exists a need for “improved drag reducing
`agents capable of reducing the pressure drop associated with the turbulent
`flow of low API gravity and/or high-asphaltene crude oils through
`pipelines.” Id. at 1:49–54. The subject matter of the disclosed invention,
`therefore, “relates generally to high molecular weight drag reducers for use
`in crude oils.” Id. at 1:15–16. More specifically, the ’249 patent discloses a
`method for reducing the pressure drop associated with flowing a liquid
`hydrocarbon through a conduit, such as a pipeline. Id. at 2:48–50. The
`method comprises introducing a drag reducing polymer into a liquid
`
`
`2 The specification defines API gravity as “the specific gravity scale
`developed by the American Petroleum Institute for measuring the relative
`density of various petroleum liquids.” Id. at 3:50–54.
`4
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`IPR2016-01901
`Patent 8,450,249 B2
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`hydrocarbon having an asphaltene content of at least 3 weight percent and an
`API gravity of less than about 26° to produce a treated liquid hydrocarbon
`wherein the viscosity is not less than the viscosity of the liquid hydrocarbon
`prior to treatment with the drag reducing polymer. Id. at 18:62–19:5.
`The ’249 patent provides several examples of suitable heavy crude oils and
`blended heavy crude oils. Id. at 4:25–34, Table 1.
`The specification further explains that, “[i]n order for the drag
`reducing polymer to function as a drag reducer, the polymer should dissolve
`or be substantially solvated in the liquid hydrocarbon.” Id. at 11:16–18.
`The liquid hydrocarbon and the drag reducing polymer, therefore, have
`solubility parameters that can be determined according to known methods.
`Id. at 4:9–21 (setting forth known methods for determining the solubility
`parameter of the liquid hydrocarbon), 11:26–64 (setting forth known
`methods for determining the solubility parameter of the drag reducing
`polymer).
`C.
`Illustrative Claim
`Claims 1, 4, and 5 are independent claims of the ’249 patent. Claim 1
`is illustrative of the challenged claims and recites:
`1.
`A method comprising:
`introducing a drag reducing polymer, into a pipeline, such that
`the friction loss associated with the turbulent flow through
`the pipeline is reduced by suppressing the growth of
`turbulent eddies, into a liquid hydrocarbon having an
`asphaltene content of at least 3 weight percent and an API
`gravity of less than about 26° to thereby produce a treated
`liquid hydrocarbon wherein the viscosity of the treated
`liquid hydrocarbon is not less than the viscosity of the liquid
`
`5
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`IPR2016-01901
`Patent 8,450,249 B2
`
`
`Statutory Basis Claim Challenged
`§ 103(a)
`1–5
`
`hydrocarbon prior to treatment with the drag reducing
`polymer;
`wherein the drag reducing polymer is added to the liquid hydrocarbon
`in the range from about 0.1 to about 500 ppmw and
`wherein a plurality of the repeating units comprise a
`heteroatom.
`Ex. 1003, 18:62–19:10.
`Instituted Grounds of Unpatentability
`D.
`We instituted an inter partes review of claims 1–5 of the ’249 patent
`on two grounds. Dec. 27.
`Reference(s)
`Holtmyer Publication,3 Holtmyer
`Patent,4 and Carnahan5
`Inaoka6 and Carnahan
`
`§ 103(a)
`
`1–5
`
`
`Petitioner relies on the declarations of Thomas H. Epps, III, Ph.D.
`
`(Ex. 1041; Ex. 1115 (public version)). Patent Owner relies on the
`declaration of Brian Dunn, Ph.D. (Ex. 2141 (public version)).
`
`
`3 Marlin D. Holtmyer & Jiten Chatterji, Study of Oil Soluble Polymers as
`Drag Reducers, 20 POLYMER ENG’G & SCI. 7, 473–77 (1980) (“Holtmyer
`Publication”) (Ex. 1005).
`4 U.S. Patent No. 3,758,406, issued September 11, 1973 (“Holtmyer Patent”)
`(Ex. 1006).
`5 Norman F. Carnahan, Precipitation of Asphaltenes in Heavy Oil and Tar
`Sands, in 40B DEV. IN PETROLEUM SCI., ASPHALTENES AND ASPHALTS, 2
`319–33 (Teh Fu Yen & George V. Chilingarian eds., 2000) (“Carnahan”)
`(Ex. 1008).
`6 European Pat. App. No. EP 0,882,739 A2, published December 9, 1998
`(“Inaoka”) (Ex. 1007).
`
`
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`6
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`IPR2016-01901
`Patent 8,450,249 B2
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`II.
`
`ANALYSIS
`
`A. Claim Construction
`In an inter partes review, claim terms in an unexpired patent are
`interpreted according to their broadest reasonable constructions in light of
`the specification of the patent in which they appear. See 37 C.F.R.
`§ 42.100(b); Cuozzo Speed Techs., LLC v. Lee, 136 S. Ct. 2131, 2144–46
`(2016) (upholding the use of the broadest reasonable interpretation
`standard). Under the broadest reasonable construction standard, claim terms
`are presumed to have their ordinary and customary meaning, as would be
`understood by one of ordinary skill in the art in the context of the entire
`disclosure. In re Translogic Tech., Inc., 504 F.3d 1249, 1257 (Fed.
`Cir. 2007). Only those terms which are in controversy need to be construed,
`and only to the extent necessary to resolve the controversy. See Nidec
`Motor Corp. v. Zhongshan Broad Ocean Motor Co., 868 F.3d 1013, 1017
`(Fed. Cir. 2017) (“we need only construe terms ‘that are in controversy, and
`only to the extent necessary to resolve the controversy’”) (quoting Vivid
`Techs., Inc. v. Am. Sci. & Eng’g, Inc., 200 F.3d 795, 803 (Fed. Cir. 1999)).
`Petitioner submits that we need not construe any claim term for
`purposes of this decision. Pet. 14. Patent Owner does not appear to propose
`any claim constructions in its Response. We determine that no claim terms
`require construction.
`B. Level of Ordinary Skill in the Art
`Petitioner proposes a detailed definition of one of ordinary skill in the
`art. Pet. 11–13 (citing Ex. 1041 ¶¶ 18–20, 22, 42). Patent Owner does not,
`in its Response, appear to dispute this definition. In light of the evidence
`before us, we adopt Petitioner’s definition of one of ordinary skill in the art.
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`IPR2016-01901
`Patent 8,450,249 B2
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`We also find that Petitioner’s proposed level of skill in the art is reflected by
`the references themselves. See Okajima v. Bourdeau, 261 F.3d 1350, 1355
`(Fed. Cir. 2001) (“the absence of specific findings on the level of skill in the
`art does not give rise to reversible error ‘where the prior art itself reflects an
`appropriate level and a need for testimony is not shown.’”); In re GPAC,
`Inc., 57 F.3d 1573, 1579 (Fed. Cir. 1995) (finding that the Board of Patent
`Appeals and Interferences did not err in concluding that the level of ordinary
`skill in the art was best determined by the references of record).
`C. Overview of the Asserted References
`1. Holtmyer Publication
`The Holtmyer Publication, titled “Study of Oil Soluble Polymers as
`Drag Reducers,” was published in 1980. Ex. 1005, 473. The Holtmyer
`Publication is directed to an investigation “undertaken to find the most
`effective material which would reduce the friction coefficient in turbulent
`flow when added in small quantities to oil pipelines.” Id. at Abstract. A
`decrease in friction loss “would allow lower energy consumption or
`alternatively an increased flow rate under the original pumping conditions,”
`making a decrease in friction loss “desirable” and “economically profitable
`to industrial organizations engaged in movement of large volumes of liquid
`at high flow rates for considerable distance as in hydraulic fracturing of oil
`and gas wells.” Id. at 473. Among the polymers for drag reduction
`synthesized and described by the Holtmyer Publication is poly(isodecyl
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`IPR2016-01901
`Patent 8,450,249 B2
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`methacrylate) (“iDMA”), which was tested for drag reduction in kerosene,
`QC-1156, Cardium, and Ellenberger. Id. at 476, Table 9.
`2. Holtmyer Patent
`The Holtmyer Patent, titled “Methods and Compositions for Reducing
`Frictional Pressure Loss in the Flow of Hydrocarbon Liquids,” issued
`in 1973. Ex. 1006. The Holtmyer Patent relates to “methods and
`compositions for reducing the frictional pressure loss encountered in the
`turbulent flow of hydrocarbon liquids through a conduit.” Id. at 1:15–18.
`Regarding frictional pressure loss encountered in the turbulent flow of
`hydrocarbon liquids, the Holtmyer Patent provides that “considerable energy
`generally in the form of pumping horsepower must be expended” in order to
`compensate for such pressure loss and, thus, “reduction of the frictional
`pressure loss in the flow of such hydrocarbon liquids brings about an
`advantageous reduction in horsepower requirements, or alternatively, an
`increased flow rate of the hydrocarbon liquids under the same pumping
`conditions.” Id. at 1:56–65. The Holtmyer Patent provides examples of
`“suitable monomers which may be utilized to form the polymer additives of
`the present invention.” Id. at 3:3–20. When using the polymer additive
`“with a well-treating fluid containing sand or other solid agent suspended
`therein,” the Holtmyer Patent states that “it is preferable to use a somewhat
`larger amount of the polymer additive.” Id. at 4:63–67.
`3. Inaoka
`Inaoka, titled “High Molecular Weight Polymer and Producing
`Method the Same and Drag Reducer,” relates to a method of producing a
`high molecular weight polymer in which “dissolved oxygen existing in a
`solvent in a radical polymerization reaction is removed, and to a high
`
`
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`IPR2016-01901
`Patent 8,450,249 B2
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`molecular weight polymer obtained by the same, and to a drag reducer.”
`Ex. 1007, 2:5–7. Inaoka describes, generally, the problems with transporting
`“an organic liquid such as crude oil” through a pipeline, caused by “the fact
`that transporting pressure on the liquid is lost by the friction generated
`between the liquid and the conduit.” Id. at 3:9–11. To suppress such
`pressure loss, Inaoka states that “a drag reducer has been used
`conventionally,” and the drag reducer includes a high molecular weight
`polymer. Id. at 3:14–15. Regarding production of such polymers, Inaoka
`states that “a method disclosed in USP No. 3,758,406 [the Holtmyer Patent]
`is known.” Id. at 3:27. Regarding specific polymer additives, Inaoka states
`that “2-ethylhexylacrylate (2EHA (carbon number of 8)) and 2-
`ethylhexylmethacrylate (2EHMA (carbon number of 8)) are particularly
`preferable.” Id. at 4:48–50.
`4. Carnahan
`Carnahan, titled “Precipitation of Asphaltenes in Heavy Oil and Tar
`Sands,” is a chapter of a textbook titled “Asphaltenes and Asphalts, 2.”
`Ex. 1008. Carnahan discloses solubility parameters of asphaltenes and of
`petroleum fluids, particularly, that the expected value of the solubility of
`heavy petroleum fluids is about 8–10 hildebrands (wherein 10 hildebrands is
`equivalent to 20.5 MPa1/2). Id. at 325. Carnahan also discloses that the
`solubility parameter of certain asphaltenes is about 20.5 MPa1/2. Id. at 324.
`D. Analysis
`A patent claim is unpatentable under 35 U.S.C. § 103(a) if the
`differences between the subject matter sought to be patented and the prior art
`are such that the subject matter as a whole would have been obvious to a
`person of ordinary skill in the art at the time the invention was made. KSR
`
`
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`IPR2016-01901
`Patent 8,450,249 B2
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`Int’l Co. v. Teleflex Inc., 550 U.S. 398, 406 (2007). Obviousness is resolved
`based on underlying factual determinations, including: (1) the scope and
`content of the prior art; (2) any differences between the claimed subject
`matter and the prior art; (3) the level of ordinary skill in the art; and (4)
`objective evidence of nonobviousness, i.e., secondary considerations. See
`Graham v. John Deere Co., 383 U.S. 1, 17–18 (1966).
`Petitioner bears the burden of proving unpatentability of the
`challenged claims, and the burden of persuasion never shifts to Patent
`Owner. Dynamic Drinkware, LLC v. Nat’l Graphics, Inc., 800 F.3d 1375,
`1378 (Fed. Cir. 2015). Petitioner must demonstrate obviousness by a
`preponderance of the evidence. 35 U.S.C. § 316(e); 37 C.F.R. § 42.1(d); see
`also Harmonic Inc. v. Avid Tech., Inc., 815 F.3d 1356, 1363 (Fed. Cir. 2016)
`(citing 35 U.S.C. § 312(a)(3) (requiring inter partes review petitions to
`identify “with particularity . . . the evidence that supports the grounds for the
`challenge to each claim”)). A party that petitions the Board for a
`determination of obviousness must show that “a skilled artisan would have
`been motivated to combine the teachings of the prior art references to
`achieve the claimed invention, and that the skilled artisan would have had a
`reasonable expectation of success in doing so.” Procter & Gamble Co. v.
`Teva Pharm. USA, Inc., 566 F.3d 989, 994 (Fed. Cir. 2009) (quoting Pfizer,
`Inc. v. Apotex, Inc., 408 F.3d 1348, 1361 (Fed. Cir. 2007)). We analyze both
`parties’ arguments, below, in accordance with the above-stated principles.
`1. Petitioner’s Ground 1—Asserted Obviousness Based on the
`Holtmyer Publication, the Holtmyer Patent, and Carnahan
`Petitioner asserts that a person of ordinary skill in the art would have
`been led from the above-referenced disclosures of the Holtmyer Publication,
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`the Holtmyer Patent, and Carnahan, to a method comprising all of the
`elements recited in claims 1–5. Pet. 20–33, 46–51.
`Petitioner argues that the “Holtmyer Publication discloses most of the
`limitations of claim 1.” Id. at 21. In the section of the Petition summarizing
`the Holtmyer Publication, Petitioner characterizes the Holtmyer Publication
`as describing an investigation “to find the most effective material which
`would reduce the friction coefficient in turbulent flow when added in small
`quantities to oil pipelines” and as describing “the problem of frictional
`pressure losses associated with the turbulent flow of a fluid through a
`conduit.” Id. at 14–15 (citing Ex. 1005, 473, Abstract). Petitioner further
`notes that the Holtmyer Publication describes the drag reducing properties of
`“a series of homo- and copolymers of alkyl styrenes, acrylates, and
`methacrylates in hydrocarbon solvents.” Id. at 15 (citing Ex. 1005, 473,
`474, Table 1). Specifically, Petitioner focuses on the Holtmyer Publication’s
`preparation and testing of iDMA, which test results are presented in Table 9
`of the Holtmyer Publication. Id. at 15–16 (citing Ex. 1005, Table 9). The
`test results demonstrate iDMA’s drag reduction in kerosene, in two types of
`crude oil (Cardium and Ellenberger), and in QC-1156 (primarily an aromatic
`hydrocarbon with an API gravity of 22.5°). Id. at 16 (citing Ex. 1005,
`Table 9).
`Petitioner relies on Dr. Epps’s testimony that “a person of ordinary
`skill in the art would have known that a plurality of the repeating units of the
`iDMA polymer comprise oxygen heteroatoms.” Id. at 21–22 (citing
`Ex. 1041 ¶ 57). Petitioner further relies on Dr. Epps’s testimony that a
`person of ordinary skill in the art would have understood that introduction of
`the iDMA polymer into a liquid hydrocarbon would reduce “friction loss
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`associated with the turbulent flow through the pipeline . . . by suppressing
`the growth of turbulent eddies” as recited in claim 1. Id. at 22 (citing
`Ex. 1041 ¶ 71). Regarding the claim 1 requirement that “the viscosity of the
`treated liquid hydrocarbon is not less than the viscosity of the liquid
`hydrocarbon prior to treatment with the drag reducing polymer,” Petitioner
`relies on Dr. Epps’s testimony that adding the iDMA drag reducing polymer
`of the Holtmyer Publication to a liquid hydrocarbon would achieve this
`effect. Id. at 23 (citing Ex. 1041 ¶¶ 76–77). Finally, Petitioner relies on
`Dr. Epps’s testimony that the Holtmyer Publication would have directed a
`person of ordinary skill in the art to add iDMA to a liquid hydrocarbon, such
`as that defined by the claims of the ’249 patent, “at a concentration within
`the ‘about 0.1 ppmw to about 500 ppmw’ range recited by claim 1,’”
`specifically, at a concentration of about 300 ppm. Id. at 23–24 (citing
`Ex. 1041 ¶¶ 72–75; Ex. 1005, Table 6).
`Petitioner posits that the “only limitation of claim 1 that the Holtmyer
`Publication does not disclose explicitly is the introduction of the iDMA drag
`reducing polymer into a liquid hydrocarbon having an asphaltene content of
`at least 3 weight percent,” (id. at 24) but argues that (i) crude oils having the
`claimed properties were well known, as acknowledged in the ’249 patent
`itself and other contemporaneous publications (id. at 25 (citing Ex. 1003,
`Table 1; Ex. 1017, 12; Ex. 1018, 557–58)); (ii) one of ordinary skill would
`have been prompted by the known economic benefits associated with drag
`reduction to introduce the iDMA polymer into a crude oil having the
`claimed properties (id. at 25–27 (citing Ex. 1005, 473; Ex. 1041 ¶¶ 90–92));
`and (iii) one of ordinary skill would have had a reasonable expectation that
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`the iDMA polymer would be effective at reducing drag in a crude oil having
`the claimed properties (id. at 27–33 (citing Ex. 1041 ¶¶ 94–111)).
`Regarding asphaltene, Petitioner argues the Holtmyer Patent addresses
`the effect of asphaltene content on the ability of the iDMA polymer to
`achieve drag reduction, relying on Dr. Epps’s testimony that “the optimum
`quantity of polymer to be introduced to a hydrocarbon liquid may vary
`depending on the type of liquid hydrocarbon involved” and that “when a
`solid agent is suspended in the liquid hydrocarbon, it is preferable to use a
`somewhat larger amount of the polymer additive,” such as between
`about 160 ppm and 1600 ppm. Id. at 27–28 (citing Ex. 1041 ¶ 97 (citing
`Ex. 1006, 4:51–59, 4:63–75)). Regarding solubility, Petitioner argues that
`solubility parameters “were (and are) commonly consulted in order to
`predict solubility of one compound in another.” Id. at 29 (citing Ex. 1041 ¶
`100). Petitioner relies on Carnahan (Ex. 1008, 325) and Dr. Epps’s
`calculations of the solubility parameters of heavy, asphaltenic crude oils
`(“within the range between about 16.4 MPa1/2 and 20.5 MPa1/2,” Ex. 1041
`¶ 107) and the iDMA polymer (“about 17.84 MPa1/2,” Ex. 1041 ¶¶ 101–03)
`to argue that because the solubility parameter of the iDMA polymer falls
`squarely within the range disclosed by Carnahan, a person of ordinary skill
`in the art “would have had a reasonable expectation that the iDMA drag
`reducing polymer would be effective at achieving drag reduction in a liquid
`hydrocarbon having an API gravity less than about 26° and an asphaltene
`content of at least 3 weight percent undergoing turbulent flow through a
`pipeline.” Pet. 33 (citing Ex. 1041 ¶ 111).
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`2. Petitioner’s Ground 2—Asserted Obviousness Based on Inaoka
`and Carnahan
`Petitioner asserts that a person of ordinary skill in the art would have
`been led from the above-referenced disclosures of Inaoka and Carnahan to a
`method comprising all of the elements recited in claims 1–5. Pet. 33–44,
`46–51.
`Petitioner argues that “Inaoka discloses most of the limitations of
`claim 1.” Id. at 34. In the section of the Petition summarizing Inaoka,
`Petitioner characterizes Inaoka as describing a high molecular weight
`polymer having a straight-chain structure with less branching, being soluble
`in an organic solvent, and “suitably adopted as a drag reducer.” Id. at 17
`(quoting Ex. 1007, Abstract). Petitioner further characterizes Inaoka as
`describing the problem of frictional pressure losses associated with the
`turbulent flow of fluid through a conduit and the conventional use of drag
`reducers to address the problem of pressure loss. Id. at 17–18 (quoting
`Ex. 1007, 3:9–13, 3:14–21). Petitioner notes that Inaoka refers to drag
`reducing polymers that may be produced by “a method disclosed in USP
`No. 3,758,406 [the Holtmyer Patent].” Id. at 18 (quoting Ex. 1007, 3:27).
`Inaoka’s drag reducing polymer “can be suitably adopted in transporting of
`an organic liquid such as crude oil through a conduit, such as a pipeline.”
`Id. at 19 (quoting Ex. 1007, 17:1–5). Inaoka’s two “particularly preferable”
`drag reducing polymers are 2-ethylhexylacrylate (“2EHA”) and 2-
`ethylhexylmethacrylate (“2EHMA”); the latter, according to Dr. Epps, is the
`same as Polymer A of the ’249 patent. Id. at 19–20 (citing Ex. 1007, 4:48–
`50; Ex. 1041 ¶ 155).
`Petitioner relies on Dr. Epps’s testimony that “a person of ordinary
`skill in the art would have known that a plurality of the repeating units of the
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`2EHMA polymer comprise oxygen heteroatoms.” Id. at 34–35 (citing
`Ex. 1041 ¶ 156). Petitioner further relies on Dr. Epps’s testimony that “a
`person of ordinary skill in the art would have understood that introducing the
`2EHMA polymer into crude oil flowing through a pipeline would reduce
`drag by suppressing the growth of turbulent eddies” as recited in claim 1.
`Id. at 35–
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