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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`\é%/%/\é%/\é%/\é
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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
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`Substituted Olefins
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`DECLARATION OF RAJIV RATNA SINGH
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`1.
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`My name is Rajiv Ratna Singh.
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`I am one of the inventors named in U.S. Patent No.
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`8,065,882 (the ‘882 patent).
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`I am a named inventor on over 100 issued U.S. Patents.
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`I am currently
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`employed by the Patent Owner of the ‘882 patent, Honeywell International Inc. Attached as Exhibit A to
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`this declaration is a copy of my recent curriculum vitae.
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`2.
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`My educational background is as follows:
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`I received my B.Sc. degree (Honours in
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`Chemistry) in 1978 from the Benares Hindu University, India.
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`I received my Ph.D. degree in physical
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`chemistry in 1987 from the University of Tennessee, Knoxville, Tennessee.
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`I conducted Postdoctoral
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`Research from 1987 to 1989 at the University of California, Berkeley. In 1996, I received my MBA
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`degree from Canisius College, Buffalo, New York.
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`3.
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`My post—university work experience is as follows:
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`I joined Honeywell International Inc.
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`(formerly AlliedSignal) in 1989. From 1989 to 1992 my title was Research Chemist, and I was
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`responsible for supplying data needed for products and process development. From 1992 to 1995 my title
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`was Senior Research Chemist. In this position I had direct supervisory responsibility for the four—member
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`Physical Measurement group. From 1995 to 2003, my title was Senior Principal Scientist. In this
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`position I had direct supervisory, project management and budgetary responsibility for the Physical
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`Science Department, whose members work on a wide spectrum of projects ranging from technical support
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`of existing products to process, product and applications development. From 2003 to 2008 my title was
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`Fellow & Leader, New Applications Department. Here I had direct supervisory, project management and
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`budgetary responsibility for the New Applications Department. From 2008 until 2010, my title had been
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`Arkema Exhibit 1062
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`Page 1 of 8
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`Arkema Exhibit 1062
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`Senior Fellow & Leader, Fluorine Chemistry Group. From 2010 to present my title is Corporate Fellow
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`& Leader Fluorine Chemistry Group. My responsibilities include direct supervisory, project management
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`and budgetary responsibility for the New Applications, Analytical Chemistry and Synthetic Chemistry
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`departments.
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`4.
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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; 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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`5.
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`I have reviewed and understand the claims being filed in connection with the response to
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`the first office action in the above—identif1ed matter (hereinafter “the Response”).
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`6.
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`Attached as Exhibit B is a Declaration of George Rusch (hereinafter the “Rusch Dec”)
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`establishing testing that has been done by the Patent Owner in connection with within the scope of the
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`claims presented with the Response. The Rusch Declaration also describes testing done by DuPont on
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`HFO—l225zc.
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`I understand that this Declaration was submitted to the Patent Office during the
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`prosecution of one of the patent application that led to the ‘882 patent.
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`7.
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`According to the DuPont publication, HFO—l225zc——within the general teaching of the
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`Inagaki reference but outside the scope of the present claims because it does not have at least one H on
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`the unsaturated tenninal carbon——has an acute toxicity, as measured by its LC50, of less than 2000 ppm.
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`The LC50 is the median lethal concentration required to kill half the members of a tested population. The
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`acute toxicity exhibited by HFO— l225zc renders this molecule unacceptable for many commercial
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`refrigeration applications, including most air conditioning applications and particularly for use in
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`automotive air conditioning.
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`8.
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`Compared to molecules within the requirements of the present claims, HFO—l225zc is the
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`closest molecule for which acute toxicity test data was publically available at the time the invention was
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`made. Accordingly, this prior art report demonstrating highly detrimental toxicity clearly teaches away
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`from, or at the very least would dissuade those skilled in the art from using, compounds of this type.
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`9.
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`The Rusch Dec also explains acute toxicity testing done by Patent Owner on another
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`molecule (2,3,3,3—tetrafluoropropene or HFO—l234yf) comparable to those reported with respect to HFO—
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`l225zc. More specifically, HFO—1234yf has the molecular structure depicted below:
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`;C1:\';
`ELI
`— THE C"
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`F “T : A "
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`HFO—1234yf
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`This molecule is structurally similar to the acutely toxic HFO—l225zc, but it also differs in a way that
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`brings it within the scope of the claims, namely, it has at least one H on the unsaturated terminal carbon
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`as opposed to two Fs in that position. Toxicity testing on this molecule establishes that it has an acute
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`toxicity of greater than 400,000 ppm. This is a value that represents an acute toxicity that is at least
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`approximately 200 times less than HFO—l225zc.
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`10.
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`Based on my knowledge and understanding of the state of the art at the time our
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`invention was made, the important and significant difference in acute toxicity described above was not
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`predictable or in any way expected. Furthennore, those compounds which have an acute toxicity on the
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`level exhibited by HFO—l225zc are generally excluded on the basis thereof from use in many refrigeration
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`applications, including particularly methods of cooling air (air conditioning), because of the potential of
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`the molecule to leak into the air space being conditioned.
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`ll.
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`The acute toxicity properties exhibited by HFO—l234yf have established that it is a viable
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`candidate for use in high concentrations as a refrigerant in commercial air conditioning applications
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`(including methods of cooling air in an automobile). In contrast, HFO—l225zc has an acute toxicity that
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`has effectively eliminated it for use as a refrigerant in most air conditioning applications and in particular
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`in automobile air conditioning.
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`l2.
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`HFO—l225zc (l, l,3,3,3—pentafluoropropene (F3C—CH=CF2)) is a compound falling within
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`the general disclosure of Inagaki and exhibiting unacceptably high acute toxicity as noted above.
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`Although toxicity is not a predictable property, it was generally believed at the time of Patent Owner’s
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`invention that the unacceptable toxicity of HFO—l225zc was due, at least in part, to the double bond. Its
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`toxicity generally excludes its use in many refrigeration applications, including particularly automobile
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`air conditioning applications because of the potential of the molecule to leak into the air space being
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`conditioned.
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`13.
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`To my knowledge, after more than ten years since the publication of Inagaki, and indeed
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`up until our invention, no one ever used any of the HFOs disclosed in Inagaki for a commercial cooling
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`application until the Patent Owner’s invention.
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`14.
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`I explain in the paragraphs below, that a heat transfer composition using an HFO, namely
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`HFO—1234yf (a compound falling within Formula II as further limited by the claims) has been widely
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`recognized and lauded by industry experts/organizations as the preferred solution for an important long
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`felt, but otherwise unresolved, need which was initially met with failure and skepticism by others.
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`15.
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`The invention of the present claims addresses the long—felt—but—unmet need for
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`developing environmentally friendly heat transfer compositions that have a minimal effect on both ozone
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`depletion (as measured by their ODP values) and global wanning (as measured by their GWP values).
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`This need has existed for many decades as atmospheric scientists began to more fully understand ozone
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`depletion and global wanning, as well as the negative contribution of fluorochemicals to these
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`environmental phenomena. The history of the international community’s understanding and regulation of
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`ozone depletion is documented in the United Nations Environment Programme’s 2000 publication
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`“Action on Ozone,” attached as Exhibit C. Important milestones include the signing and ratification of
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`the 1985 Vienna Convention and the 1987 Montreal Protocol, as well as the resulting switch from
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`chlorofluorocarbons (“CFCs”) to lower—impact hydrochlorofluorocarbons (“HCFCs”) and
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`hydrofluorocarbons (“HFCs”). Although the transition away from CFCs has been an important step
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`forward, the HCFC and HFC compounds meant to replace CFC remain significant contributors to global
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`warming. Thus, their use was an imperfect solution.
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`16.
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`At the time the international community was learning about and regulating ozone
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`depletion, it was also learning about global wanning caused by greenhouse gases. However, a solution to
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`the global wanning problem was more difficult to come by than that to the ozone depletion problem, as
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`shown by the number of years that passed before alternatives having both low GWP and low ODP values
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`were proposed, as well as the frustration expressed by industry participants at finding a commercially
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`acceptable solution. CFCs have been linked to global warming since the late—l970s, as shown by a 1977
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`report by the National Academy of Sciences entitled “Energy and Climate,” attached as Exhibit D. In the
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`1980s and 1990s, industry participants explored the effect of proposed low—ODP replacement refrigerants
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`on global wanning and expressed the view that any long—term replacements for CFCs must have minimal
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`effects on both ozone depletion and global wanning. For example, a 1986 article by Lois Embler in
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`Chemistry & Engineering Weekly discussed DuPont’s decision to support CFC controls, which are due in
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`part to “[t]he contribution CFCs make to climate warming produced by carbon dioxide and other trace
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`gases.” (see page 48 of the attached Exhibit E). Similarly, a 1987 article by Mark McLinden and David
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`Didion stressed that although “[t]he problem of global wanning due to the greenhouse effect has received
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`far less attention recently than that of ozone depletion, [it] is felt by many to be equally important.” (see
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`page 33 of the attached Exhibit F). Along these lines, Donald Bivens and David Didion presented a paper
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`during a 1989 ASHRAE (“American Society of Heating, Refrigerating and Air—Conditioning Engineers”)
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`Conference (attached as Exhibit G) in which they discussed several proposed CFC—alternatives’
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`implications on global wanning. And a 1990 article by Donald Fisher that appeared in Nature attempted
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`to characterize the effect of proposed CFC replacements on global wanning and stated that although
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`“intemational conventions (Montreal 1987) regulating the future use of chlorofluorocarbons (CFCs) stem
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`from the recognition that these compounds may affect stratospheric ozone[,] [a]nother environmental
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`concern involving these compounds is their role as greenhouse gases.” (see page 513 of the attached
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`Exhibit H) Altogether, during this initial time period, the contribution of fluorochemicals to global
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`warming was understood to be an issue but progress towards an acceptable commercial solution was
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`impeded by the absence of straightforward solutions. Thus, the industry focused first on researching and
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`implementing low ODP but high GWP replacements for CFCs (z'.e., the HCFCs and HFCs). However,
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`the global wanning contribution by these replacements was addressed by the UN’s Framework
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`Convention on Climate Change (“UNFCCC”) in 1992, which in turn resulted in the 1997 Kyoto Protocol
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`on greenhouse gases. In 2006, the European Directive 2006/40/EC, later modified (Exhibit 1) was
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`enacted to phase out automobile refrigerants having GWPs greater than 150.
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`17.
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`Prior to Honeywell’s invention, proposed refrigerants either had low ODP values but
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`high GWP values, making them unacceptable for long—term implementation, or they had low ODP and
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`GWP values but required detrimental perfonnance or safety tradeoffs. As discussed, the fonner category
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`included the HCFC and HFC replacements for CFCs. The latter included HFC— 152a, carbon dioxide (R-
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`744), and hydrocarbons. For example, although HFC—152a and hydrocarbons have both low GWPs and
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`low ODPs, their high flammability posed significant safety risks for certain applications as described in
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`James Calm and David Didion’s 1997 article “Trade—Offs in Refrigerant Selections.” (Exhibit J). And
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`carbon dioxide’s thennodynamically inferior coefficient of perfonnance relative to HFC—134a limited its
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`utility for systems designed for use with HFC—134a, including current automobile air conditioning
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`equipment. For example, in wann climates, carbon dioxide is less efficient at cooling air even though this
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`is precisely where air conditioning is desired. This issue is discussed in more detail in J. Steven Brown,
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`Samuel Yana—Motta, and Piotr Domanski’s 2002 comparative article, which was published in the
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`International Journal of Refrigeration, attached as Exhibit K.
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`- Page 5 -
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`18.
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`Altogether, HCFCs, HFCs (including HFC—152a), carbon dioxide, and hydrocarbons
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`represent failures by others in the industry to develop refrigerants that solved the need for low ODP and
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`low GWP heat transfer compositions without significant tradeoffs. After many years passed without the
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`identification of acceptable low ODP and low GWP heat transfer compositions, industry commentators
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`became pessimistic about finding an acceptable solution. For example, on page 6 of the Calm and Didion
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`article referenced above opined in 1997 that: “[T]he outlook for discovery or synthesis of ideal
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`refrigerants is extremely unlikely. Trade—offs among desired objectives, therefore, are necessary to
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`achieve balanced solutions. .
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`. [T]he probability of finding an ideal refrigerant, particularly with the
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`exhaustive searches perfonned to date, is practically zero. Those waiting for a perfect solution will be
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`disappointed.”
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`19.
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`Similarly, in 1999, Dr. Denis Clodic (a renowned person with extensive experience in the
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`search for solutions in the art who was then Deputy—Director at the Center for Energy and Processes in
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`France) and Young Soo Chang expressed doubt that “HFCs can rapidly disappear” on the world scale
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`because “no simple chemical molecule that has all the desirable characteristics is currently available.”
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`(see pages 9- 10 of the attached Exhibit L, translation at Exhibit M).
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`20.
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`In light of this pessimistic outlook, Honeywell’s announcement of its commercial HFO—
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`1234yf product for automobile air conditioning, which could be used with PAG and POE lubricants, was
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`met with excitement. The following quotes from various industry and academic papers, articles, and
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`presentations illustrate the wide recognition and praise that has been achieved by the presently claimed
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`subject matter.
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`21.
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`In February of 201 1, the United States EPA issued a press release (attached as Exhibit N)
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`touting the claimed invention as a “home grown innovative solution.” In particular, the EPA stated the
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`following with respect to HFO—1234yf: “This new chemical helps fight climate change and ozone
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`depletion,” said Gina McCarthy, assistant administrator for EPA’s Office of Air and Radiation. “It is
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`homegrown innovative solutions like this that save lives and strengthen our economy.”
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`22.
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`In another article, attached as Exhibit 0 hereto, Dr. Denis Clodic, reflecting upon the
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`state of the art and on previous efforts to develop a new, environmentally acceptable refrigerant, then
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`makes the following note about Honeywell’s HFO—1234yf product: “Moreover, in February 2006, what
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`was apparently impossible became possible, namely the existence of molecules containing fluorine and
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`having a very short atmospheric life, in the case which interests us, less than two weeks. Figure 8 shows
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`a molecule of tetrafluoropropylene with a GWP of 4. which is very moderately flammable. less than R-
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`32, and for which toxicity studies to date show quite acceptable results."
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`23.
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`In an article attached as Exhibit P hereto appearing in Chemical Week in November,
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`2008, the authors called the claimed invention “revolutionary” as follows: “Separately, Arkema is
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`piloting a process for the ‘revolutionary’ R-1234yf fluorinated gas at Lyon, France.”
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`24.
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`In a July 2010 General Motors on-line article attached as Exhibit Q, entitled “GM First to
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`Market Greenhouse Gas-Friendly Air Conditioning Refrigerant in U.S.,” July 23, 2010,” it is noted that:
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`“General Motors Co. will introduce a new greenhouse gas-friendly airconditioning refrigerant in 2013
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`Chevrolet, Buick, GMC and Cadillac models in the U.S. that keeps vehicle interiors as cool as today
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`while reducing heat-trapping gases in the atmosphere by more than 99 percent. The biggest benefit of the
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`new refrigerant, (HFO-1234 yf) supplied by Honeywell, is that it breaks down faster in the atmosphere
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`than the refiigerant currently used (R—134a). On average, R— 1 34a refi'igcrant has an atmospheric life of
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`more than 13 years, giving it a global warming potential ( GWP) of over 1,400. The use of IIFO-1234yf
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`will help GM vehicles significantly exceed its targets under the new regulations.
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`. GM‘s decision to
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`adopt this new refrigerant is additional proof of our commitment to be on the forefront of green
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`technologies that will keep our planet healthy for our children and grand-children,” said Mike Robinson,
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`GM vice president of Environment, Energy and Safety Policy. “lt’s not just about meeting regulatory
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`requirements; it’s about environmental leadership and GM plans to lead in developing new technologies
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`that will take the vehicle out of the environmental debate."
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`25.
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`Such praise has even been echoed by the German automotive industry (the Verband der
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`Automobilindustrie or “VDA") (attached as Exhibit R), which at one point was encouraging the use of
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`carbon dioxide but is now supporting the use of HFO- l234yf: “[HFO-l234yf] has received global
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`acceptance .
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`.
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`. and is significantly better than the coolant Rl34a that was previously used. These exciting
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`advantages make R1234yf a viable choice for use around the world."
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`26.
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`I declare that all statements made herein of my own knowledge are true and that all
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`statements made on information and belief are believed to be true; and further that these statements are
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`made with the knowledge that willful false statements are punishable by fine or imprisonment, or both,
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`under §l00l of Title 18 of the United States Code and that such willful false statements may jeopardize
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`the validity of the claims or the patent.
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`E 2,/24/2i} E. 2
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