IN THE UNITED STATES PATENT AND TRADEMARK OFFICE
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`Mail Stop: Inter Partes Reexam
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`Attn: Central Reexamination Unit
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`Examiner: Ling Xu
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`Art Unit: 3991
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`xax./\/xas/xas/xa
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`In re Reexam Control No. 95/002,030
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`Filed: August 20, 2012
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`U.S. Patent No. 8,065,882 to Singh et al.
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`Title: Compositions Containing
`Fluorine Substituted Olefins
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`DECLARATION OF DONALD B. BIVENS
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`1.
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`My name is Donald Bivens. I joined DuPont Company in 1966, and held a number of
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`technical and managerial positions in plastics, fiber intermediates, and fluorochemicals. My work
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`focused on fluorochemicals from 1981 to 2009, during which time I worked in refrigerants process
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`technology management as well as research and development of new alternatives for CFC and HCFC
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`saturated compounds} I have since retired from DuPont, and am now an independent consultant on
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`issues related to refrigerant applications. Attached as Exhibit A to this declaration is a copy of my recent
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`curriculum vitae. I received my B.S. degree in Chemical Engineering in 1962 from the University of
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`Tennessee. I received my M.S. and Ph.D. degrees in Chemical Engineering from the Georgia Institute of
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`Technology in 1963 and 1966.
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`2.
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`I am the principal author or co-author of more than 100 peer-reviewed journal articles,
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`patents, presentations, and other publications related to the use of refrigerants and including methods of
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`cooling air. A representative list of such publications is provided in my curriculum vitae. Many of the
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`patents on which I am a named inventor were found to be commercially significant by DuPont and were
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`commercialized.
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`3.
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`I have worked with refrigeration companies, air conditioning companies, industry groups,
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`and academic and governmental laboratories to facilitate the safe and environmentally sustainable
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`application of new refrigerants. Thus, I have considerable experience in specific applications, including
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`1 By “CFC” I am referring to compounds commonly known in the refrigerants industry as chlorofluorocarbons. By
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`“HCFC” I am referring to compounds commonly known in the refrigerants industry as hydrochlorofluorocarbons.
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`CFCs and HCFCs have fully saturated carbon backbones in which the carbon atoms are all connected by single
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`bonds. CFCs and HCFCs typically are one or two carbon atom compounds containing chlorine, and fluorine atoms
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`(CFCs) and chlorine, hydrogen, and fluorine atoms (HCFCs).
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`- Page 1 -
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`Page 1 of 11
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`Arkema Exhibit 1059
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`Arkema Exhibit 1059
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`methods for cooling air. Additionally, I have participated in technology evaluation teams for National
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`Institute of Standards and Technology (NIST) refrigerant programs, and Oak Ridge National Laboratory
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`(ORNL) Buildings Technology programs. Since 2009, I have served on three Department of Energy
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`Merit Review Committees where I evaluated research proposals for improving building energy efficiency.
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`I am currently a member of the ASHRAE Research Administration Committee, having responsibility for
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`evaluation and recommendation for funding of research proposals from the ASHRAE technical
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`committees.
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`4.
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`I am a member of the following professional organizations, with past and current
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`committee positions: Chair of the American Society of Heating, Refrigerating, and Air Conditioning
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`Engineers (ASHRAE) Refrigerants Committee; Chair of the ASHRAE Refrigerants Thermophysical
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`Properties Subcommittee; Chair of the ASHRAE Refrigerants Research Subcommittee; Chair of the
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`ASHRAE SSPC34 Designations and Nomenclature Subcommittee; Member of the ASHRAE Standards
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`Committee; Member of the ASHRAE Refrigerants Committee; Current voting member of the ASHRAE
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`Committee to draft the standard on the reduction of refrigerant emissions from systems; Current voting
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`member of the ASHRAE Research Administration Committee; Reviewer for the ASHRAE technical
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`publications and International Journal of Refrigeration; Convener of the ASHRAE sponsored committee
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`which developed refrigerants thermophysical properties standard for the International Standards
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`Organization (ISO 1758422005); Member of the Air Conditioning and Refrigeration Institute (ARI)
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`Alternative Refrigerants Evaluation Program; Member of the ARI Refrigerants Subcommittee; Member
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`of the ARI Twenty-First Century Working Fluids Subcommittee; Member of the International Energy
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`Agency Heat Pump Team for the United States; Member of the Technical Options Committee for the
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`Montreal Protocol; Lead Author for Chapter 4 (“Refrigeration”) of the Intergovernmental Panel on
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`Climate Change’s (IPCC) Working Group III Report entitled “Safeguarding the Ozone layer and the
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`Global Climate System.”
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`5.
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`I have received the following honors and awards: R.C. Schulze Award for Distinguished
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`Service from the ARI; ASHRAE Distinguished Service Award; DuPont Company Award for the
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`development of new refrigerant alternatives technology; Hero of Chemistry Award from the American
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`Chemical Society for the development of alternative refrigerant blends; Cited for contributing to the
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`award of the 2007 Nobel Peace Prize to the IPCC.
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`6.
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`I have reviewed and am familiar with the following documents from the ‘882 patent
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`reexamination: U.S. Patent No. 8,065,882 (“the ‘882 patent”) and pending claims; October 23, 2012
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`Office Action by the Examiner; U.S. Patent No. 6,783,691 (“Bivens”); JP 04110388 (“Inagaki”); U.S.
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`Patent No. 6,374,629 (“Oberle”); U.S. Patent No. 4,842,024 (“Palinchak”); U.S. Patent No. 6, 176,102
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`(“Novak”); and declarations of Honeywell personnel provided to the PTO.
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`7.
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`I consider myself a person skilled in the art of heat transfer methods and compositions
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`originally claimed and now pending in the ‘882 patent;2 and believe that I have the requisite knowledge
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`that allows me to interpret the art as it would have been understood by one having ordinary skill in the art
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`at the time the invention was made (in 2002).
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`8.
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`Prior to 2002, all commercial fluorocarbon-based heat transfer compositions for cooling
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`or conditioning air (even in automobiles) had used only saturated refrigerants--that is, compounds with
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`only carbon-carbon single bonds, not carbon-carbon double bonds as found in the halogenated olefins
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`(HFOs) of the methods of the ‘882 patent. Importantly, HFOs are chemically different from the
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`previously-used saturated refrigerants because of the presence of the double bond. This difference
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`significantly impacts the chemical and physical properties of the refrigerant such as, for example, toxicity,
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`thermal and chemical stability, flammability, miscibility with lubricants, and compatibility of
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`refrigerant/lubricant mixtures with system materials of construction.
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`The problem facing the refrigerant industry at the time of Honeywell’s inventions was to
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`find more environmentally-friendly refrigerants to replace existing refrigerants for use in automobile air
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`conditioning systems. In order to solve that problem, researchers had to contend with a complex matrix
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`of required and unpredictable properties. A heat transfer composition for automobile air conditioning
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`must possess simultaneously at least the following: excellent heat transfer and performance
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`characteristics, substantial environmental advantage (low GWP and ODP), low and acceptable toxicity
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`and flammability, acceptable refrigerant/lubricant miscibility, as well as thermal and chemical stability
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`between the refrigerant and lubricant and with materials found within the system. Thus, the problem
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`facing researchers—even those of extraordinary skill— attempting to identify solutions to this challenge
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`was not simply identifying compounds with refrigerant or heat transfer properties, but rather finding a
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`refiigerant with such properties that could then be combined with a lubricant having the appropriate
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`properties to form a composition that would satisfy the desired criteria. Honeywell’s claimed methods
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`which require the use of the claimed Formula II compounds (which include HFO-l234yf and transHFO-
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`l234ze for example) satisfy each requirement without requiring accompanying trade offs in performance
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`or safety. This was in no way predictable or thought possible at the time of the inventions.
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`2 For clarity, my reference to claims “now pending,” “now claimed” and the like is to the claims presented in the
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`Exhibit A Claim Listing that I understand is being filed concurrently with this declaration.
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`10.
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`At the time of the invention leading to the ‘882 patent, those3 searching for more
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`environmentally friendly heat transfer compositions for automobile air conditioning were confronted with
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`a sizeable field of potential candidates. Not only were researchers looking at compounds which would be
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`considered to belong to the traditional class of halogenated refrigerants (such as CFCs/I-ICFCs) and
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`identifying HFCs, they were also investigating other groups of chemically diverse compounds such as
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`fluorinated ketones, alcohols, ethers, amines, silicon and sulfi1r-containing compounds, as well as gases
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`like CO2 and NH3, to name a few. When the numerous members of each class as well as the possibility
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`of blends are considered, the number of possible candidates multiplies quickly. In all, I estimate that
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`thousands of possible compounds and blends were available for consideration at the time of Honeywell’s
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`inventions, and the search for the best candidates went in many different directions. In the search that
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`followed, industry, academia, and government research organizations began investigating options for next
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`generation heat transfer compositions. However, and despite that the search involved exploring a large
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`group of very diverse compounds, none of them recommended using any halogenated olefins, let alone
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`any of the fluorinated olefms claimed in the methods of the ‘882 patent. And there was good reason for
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`that. Fluorinated olefins at that time were viewed by the industry with a great deal of skepticism. In
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`addition to other perceived disadvantageous properties, it was generally believed these compounds were
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`too unstable and reactive due to the reactivity of the double bond.4 Reactivity is also understood in the art
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`to cause toxicity. Thus, HFOs were considered to be of no value as refrigerants in any application. Due
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`to this perception, halogenated olefins were routinely rejected in investigations for alternative refrigerant
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`replacements. This conventional thinking impacted my own search for low GWP refrigerants.
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`I was located at the DuPont Chambers Works site in the late 1980s with the assignment to
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`identify compounds that would be more environmentally friendly than CFC compounds for refrigeration
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`and air conditioning applications. I began the assignment by requesting a search and listing of all known
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`compounds in the boiling point range of about —80°C to +30°C. The resulting list contained hundreds of
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`compounds and I needed to develop criteria for reducing the listing to the compounds more likely to be
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`3 Those searching included more than 10 international chemical companies, various trade organizations and agencies
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`within the U.S. government (e.g., EPA, National Institute of Standards and Technology, and NASA), as well as
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`foreign organizations and governments.
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`4 See e.g., Exhibit F, Mark O. McLinden & David A. Didion, Questfor Alternatives: A Molecular Approach
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`Demonstrates Tradeofifs and Limitations Are Inevitable in Seeking Refiigerants, 29(l2) ASHRAE J. 32, n. 4 (1987)
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`(compounds with carbon-carbon double bonds not considered because of their lower stability); Exhibit G, J. Jones &
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`C.J. Morrissey, NASA JPL, Nearly Azeotropic Mixtures to Replace Refrigerant 12, 16(8) NASA TECH BRIEF 122,
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`tbl. 2 (1992) (dismissing the fluorinated olefms as being too reactive); Exhibit H, W.L. Kopko, Beyond CFCs:
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`Extending the Searchfor New Refiigerants, PROCEEDINGS OF ASHRAE’S 1989 CFC TECHNOLOGY CONFERENCE 39,
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`42 (1989).
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`successful in refrigeration and air conditioning applications. A Ph.D. chemist with many years of
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`experience researching fluorine containing compounds was in a nearby office and offered to help with the
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`initial screening. Based on the need for non-toxic compounds and long term stability in refrigeration and
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`air conditioning systems operating near the general public, he advised me to eliminate first from my list
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`any unsaturated compounds. I took his advice and began studies of selected remaining compounds,
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`eventually resulting in patenting and commercialization of several compounds for refrigerant applications.
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`But none of these compounds were halogenated olefins; and none satisfied the full matrix of properties
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`required.
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`12.
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`Given the above, when Honeywell announced its plans to develop the HFOs of the ‘882
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`patent for refrigeration applications, I was quite surprised. In fact, I am not aware of anyone in the
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`industry who was not surprised by the news. I can say unequivocally and without reservation that
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`Honeywell’s invention was, in my opinion, the most significant discovery that occurred during my 30
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`year career in the entire field of refrigeration.
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`13.
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`A refrigerant (in 2002 or even today) for use in methods of cooling or conditioning air in
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`an automobile must meet the difficult to achieve criteria outlined in paragraph 9 above. Although it is
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`quite challenging to find a refrigerant that meets all of the required properties, surprisingly and
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`unexpectedly, the small subset of compounds claimed in the methods of the ‘882 patent do meet these
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`requirements while other HFO compounds taught in the generic formula of Inagaki such as HFO-l243zf
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`and HFO-l225zc do not.
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`14.
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`The complexity of the problem prior to the Honeywell invention (and hence the
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`surprising results of its discovery) was borne out in the long search, repeated failures, initial skepticism,
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`acceptance and praise, and other factors described in Dr. Singh’s December 2012 declaration, paragraphs
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`14 to 25. By no means was the problem simply finding a lubricant to pair with Honeywell’s claimed
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`HFO compounds for methods of cooling air in automobile air conditioning because no HFOs were
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`accepted refrigerants at that time. Strong evidence that those skilled in the art considered fluorinated
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`olefins to be generally unacceptable for use in heat transfer compositions in general (and as a refiigerant
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`in automobile air conditioning applications specifically) is the very fact that no one in the industry had
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`developed, used or commercialized a fluorinated olefin for use in a heat transfer composition in the more
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`than 10 years post-publication of Inagaki, and even up until the present invention. It was not until
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`Honeywell’s invention that the use of any haloolefin as a refiigerant was pursued commercially.
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`Additional praise for Honeywell’s invention was bestowed on two of the Honeywell inventors on the ‘882
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`patent who received prestigious awards for the work they did related to this invention. Exhibits B and C.5
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`15.
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`A person of ordinary skill in the art would understand that Inagaki expresses no
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`preference for any one unsaturated compound (or sub-groups of unsaturated compounds) out of the 30
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`unsaturated compounds disclosed. No compound is expressly identified in Inagaki as being better or
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`worse than any other. In fact, four of the exemplified compounds are stated to be “typical compounds”
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`with no indication that any advantage is to be gained by using any one of the 30 compounds, nor any of
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`these four compounds, over any other. Certainly, Inagaki provides no teaching that a selection can be
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`made from among the general class of compounds for use in automobile air conditioning systems or that
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`the specific subset of compounds in the instant invention is any way preferred. Rather than teaching the
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`possibility of making a selection of a compound to achieve an advantage, Inagaki actually teaches that all
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`compounds are equivalent and then goes on to include as acceptable, compounds now known to have
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`unacceptable toxicity for use as a refrigerant in an automobile (e.g., HFO-l225zc). The only logical
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`conclusion from this is that Inagaki, like all others skilled in the art at that time, presumed that toxicity
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`problems would exist equally with all of the compounds within the formula and that toxicity was of little
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`to no concern for the heat pump application for which the molecules were being considered. Thus, there
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`is no teaching in Inagaki to arrive at the HFOs of the ‘882 patent method claims. In my opinion, Inagaki
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`does not make obvious the invention claimed in the ‘882 patent.
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`16.
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`Moreover, Inagaki actually teaches away from using the HFO’s of Honeywell’s
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`invention. Specifically, Examples 1 to 4 show that 3,3,3-trifluoro-1-propene (HFO-l243zf) of Example 1
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`achieves a higher capacity relative to refrigerant R-l2 than compounds including HFO-l234ze, described
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`in Example 2 and those compounds described in Examples 3 and 4 (see capacity ratio data of Figure 4
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`and examples 2-4 in which the capacity ratios of the example compounds versus R-l2 can be determined
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`from data provided).6 A person skilled in the art would conclude that the only possible preference--if it
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`5 Dr. Raj iv Singh was awarded the Jacob F. Schoellkopf Medal by the Western New York Section of the American
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`Chemical Society in 2008; the award recognizes contributions to chemistry and chemical technology constituting a
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`major advance in science (Chemical Engineering Progress, January, 2009). Dr. Ian Shankland was awarded the
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`2008 Perkin Medal by the Society of Chemical Industry; the award recognizes scientists whose innovations have led
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`to improvements in quality of life and competitiveness of the U.S. chemical industry (Chemical & Engineering
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`News, July 23, 2008). Notable recent recipients of the Perkin Medal include Gordon Moore, cofounder of Intel,
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`Herbert Boyer, cofounder of Genentech, and Robert Gore, inventor of Gore-Tex.
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`6 Using the capacity ratio data of Figure 4 and examples 2-4, the capacity ratios of the Example compounds versus
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`R12 can be determined as follows: Beginning with Example 1 (F3C-CH=CH2) data from Figure 4, the capacity ratio
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`for R12/R22 at 5 degrees C evaporator temperature is 0.61, and the ratio for the compound of Example 1 versus R22
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`is 0.68. Dividing these two ratios results in the capacity ratio for F3C-CH=CH2/R12, which is 0.68/0.61 = 1.11. The
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`could be argued that Inagaki gave any direction at all--between the 30 compounds is the teaching
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`regarding the capacities of the 4 examples. Therefore, if any preference is taught at all, it is a preference
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`for HFO-l243zf, which lies outside the compounds claimed in Honeywell’s ‘882 patent claims. But
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`HFO-l243zf is too flammable for use in automobile air conditioning.
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`17.
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`Also, a person of ordinary skill in the art would not understand Inagaki as teaching
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`methods of cooling or conditioning air. Inagaki makes no reference to automobile air conditioning or
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`even air conditioning in general. When Inagaki is read in its entirety (even with reference on page 1 to
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`“refrigerators, heat pumps and the like” relied on by the Examiner) the skilled person would conclude, at
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`most, that Inagaki is directed to methods of heat transfer in a heat pump. The term “heat pump” is used
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`numerous times (fourteen) throughout the reference and all the examples are of a heat pump. Moreover,
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`the term “refrigerator” is not the same as an “air conditioner” generally or “automobile air conditioner”
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`specifically. Although the vapor compression cycle forms the theoretical basis for many refrigeration
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`applications, specific refrigeration applications have their own technical requirements. As a result,
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`specific requirements are imposed depending on the application. This is particularly true for methods of
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`cooling air in an automobile because of the unique environment encountered--a confined and moving
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`space for passengers typically proximate a gasoline-fed engine which is subjected to a wide variety of
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`operating conditions. To be usefirl in methods of cooling air in an automobile, the refiigerant must
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`simultaneously possess a number of unique and essential properties as enumerated in paragraph 9 above.
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`18.
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`While each of the Examples identify the heat transfer media, there is not a single mention
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`in any of the Examples of the material into which heat is being transferred. There is certainly no mention
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`or indication in any of the Examples that air is involved in the heat transfer in any way, much less that
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`heat is removed from air in order to cool air. Furthermore, the use of the term “heat pump” in the Inagaki
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`Examples do not imply or inherently describe cooling of air. There are many heat pump applications in
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`which heat is transferred to water or possibly other liquids that do not involve the cooling of air at all.
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`19.
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`Figure 2 is also equally lacking any disclosure or suggestion of methods of cooling air.
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`There is nothing in Figure 2 which indicates or suggests in any way to a person skilled in the art that air
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`would be cooled as a result of the operation of the apparatus disclosed therein. In addition, the labels in
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`Fig. 2 describe water as the fluid, not air. "Fw" indicates the flow rate of the water and "Tw," the
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`capacity ratios vs R12 for Examples 2-4 are calculated in a similar manner using the ratios in Tables 2-4. For
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`Example 2 compound F3C=CH=CHF, the capacity ratio vs R22 is 0.43, and the capacity ratio for R12 is 0.61. So
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`the capacity ratio for F3C-CH=CHF/R12 is 0.43/0.6l=0.70. Accordingly the capacity ratios versus R12 for
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`Examples 3 and 4 are 0.44/0.6l=0.72 (Example 3), and 0.53/0.6l=0.87 (Example 4). The Inagaki data show that
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`Example 1 compound F3C=CH=CH2 achieves the highest capacity ratio versus R12.
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`- Page 7 -
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`Page 7 of 11
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`Page 7 of 11
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`temperature of the water in the evaporator, heat exchanger, and condenser. Inagaki states that "Figure 2 is
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`a circuit diagram of the refrigeration cycle used in the examples and comparative examples." It would be
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`assumed by the person of ordinary skill in the art that the authors of Inagaki had a specific reason for
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`showing the flow of water (not air) across the heat exchangers, rather than a simpler diagram with arrows
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`depicting air flow across the heat exchangers. To be clear, there is nothing in any of the labels in Fig. 2
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`that implies the presence of air in the system at all.
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`20.
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`My view of Fig. 2 is fl.lI'tl’l61‘ supported by an article published by the four named
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`inventors on the Inagaki patent application7 attached as Exhibit D to my declaration. At the same time
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`that Inagaki et al. provided Fig. 2 to the Japanese Patent Office, they also published and provided a
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`presentation to the worldwide refrigerant industry in 1992 at the Purdue University which included a
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`figure (Fig. 11) very similar to Fig. 2. In Exhibit D (entitled “Characteristics of HFC Refrigerants” in
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`Proceedings of the 1992 International Refrigeration Conference), as would be understood by a person of
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`ordinary skill in the art, Fig. 11 refers to liquid in the system, not air, as being the fluid from which heat is
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`transferred. Specifically, Fig. 11 shows two storage tanks, a “Low temperature tank” and a “High
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`temperature tank.” From the use of this terminology “Low temperature tank” and “High temperature
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`tank” and from this design set-up, a person skilled in the art would understand that these two tanks hold
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`liquid--not air--to ensure an even flow of liquid to the suction of the two pumps denoted just outside these
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`tanks. This is a well-known design requirement for the pumping of liquids but not air. Additionally, the
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`use of the term “pump” just outside these two tanks to denote in the same diagram the movement of both
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`heat sink and heat source fluids also indicates that the fluid moving through the system from the storage
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`tanks to the heat exchangers is a liquid and not air. Finally, there are no pressure sensors on the fluid
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`circuit which would be expected if the fluid were air and not water or some other liquid.
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`21.
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`The same technical requirements needed for automobile air conditioning are not required
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`for other types of air conditioning applications or for heat pump applications. The teaching in Inagaki
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`with its emphasis on the exemplified heat pump application would not impart to a person of ordinary skill
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`in the art any information about the use of any of the 30 compounds for automobile air conditioning.
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`There is no teaching or motivation anywhere in Inagaki that would lead the person of ordinary skill to the
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`automobile air conditioning application.
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`22.
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`Whether a refrigerant and lubricant combination (even a saturated refiigerant/lubricant
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`combination) is miscible is not predictable. In fact, the 1992 Purdue paper by Inagaki et al. (referenced in
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`7 I note that one of the four inventor