INTERNATIONAL

STATUS OF LEGAL CHALLENGES: PATENTS

RELATED TO THE USE OF HFO-1234YF IN AUTO
AIR CONDITIONING
Steve Seidel
Center for Climate and Energy Solution
Christine R. Ethridge
Eckert Seamans Cherin & Mellott, LLC
July 2016

One of the key challenges identified by Parties to the cal substitutes (i.e., primarily hydrofluoroolefins [HFOs])
Montreal Protocol as part of the Dubai Pathway on and on the compositions and use of these substitutes in a
Hydrofluorocarbons (HFCs) relates to concerns raised number of industry sectors primarily in developed (non-
about intellectual property rights. Because a large num- Article 5) and in several Article 5 Parties. The category
ber of patents on low global warming potential (GWP) of patents on compositions and their uses are generally
chemical substitutes for HFCs have been filed by a few referred to as application patents. This paper seeks to
transnational companies, a number of developing coun- address what has been described as the primary concern
tries (Article 5 Parties) have raised concerns that these related to patents—even if chemical companies in Article 5
could impede their ability to meet HFC reduction goals, Parties can develop their own methods of producing HFOs, they
significantly increase the costs of doing so, or put their would be prevented (absent a license) from selling their products
industries at a competitive disadvantage. at home and in key markets abroad in countries where applica-
Numerous patents have been granted and applications tion patents have been granted to other companies until the time
for patents filed both on methods for producing chemi- when these patents expire.

I. KEY FINDINGS
This paper focuses on application patents granted on • Two of these challenges are final determinations,
compositions for, and the use of, HFO-1234yf in the auto- while the other seven are at various stages of ap-
mobile air-conditioning sector and examines the current peals, including re-opening of prosecution.
status of legal challenges to a number of patents relevant • Patents granted in India and China on composi-
to this sector. Key findings include: tions for the use of HFO-1234yf in automobile
• Nine patents granted in the United States and air conditioning claim the same or very similar
Japan and under the European Patent Conven- subject matter to that recited in the claims con-
tion that, in the absence of a license, would tained in the nine patents that have been success-
prevent the use of HFO-1234yf in automobile air fully challenged in the United States, Europe, and
conditioning, are in various stages of challenges, Japan.
with all patent-holder claims relevant to the use of • Other patent applications (e.g., continuations in
HFO-1234yf in auto air conditioning canceled or part and divisionals1) have been filed, and other
rejected.
 patents have recently been granted (some of addition, new patents derived from these exist-
which are in early stages of being challenged), ing patents are being granted and challenges to
that are also relevant to the use of HFO-1234yf in them, if successful, will require additional time.
automobile air conditioning. • If any of the legal challenges described below
• Any conclusions from this review of legal chal- ultimately result in patents being upheld, then re-
lenges must be viewed as tentative pending new strictions resulting from the patent claims would
developments. While a number of early chal- continue through 2023–25 when they would
lenges have been successful in revoking relevant expire.
patents, in most cases appeals are still pending. In

II. APPLICATION PATENTS RELATED TO HFO-1234YF IN AUTO AIR

CONDITIONING
This paper focuses on the status of legal challenges to of these cover the use of a wide range of blends, often
a number of application patents—specifically the use involving HFO-1234yf mixed with other compounds. Be-
of HFO-1234yf in automobile air conditioning.2 This cause the automobile manufacturing sector has focused
sector was targeted because the market for its use is the its efforts on the use of HFO-1234yf alone and not in
most advanced. The automobile manufacturing sector blends, our analysis focuses only on those patents that
is already well along in its transition from HFC-134a to would impact the use of HFO-1234yf in this manner in
HFO-1234yf in developed nations, many of which have auto air conditioning.
regulations in place setting deadlines for such transi- With this limitation in mind, we have focused our
tions. While much industry effort has focused on shifting analysis on legal challenges on the following nine pat-
to HFO-1234yf, research is also being conducted on ents, shown below, that have been granted in the United
alternative secondary loop systems using HFC-152a3 and States, Japan, or by the European Patent Office.4 These
Daimler has announced that it will introduce the first patents appear to be most relevant to the use of pure
vehicles with carbon dioxide air-conditioning systems in HFO-1234yf as the refrigerant in auto air conditioning.
2017. Nonetheless, automobile manufacturers have devel- The patent holder for all nine is Honeywell. These three
oped technical standards (i.e., by the Society of Automo- jurisdictions represent the largest developed country
tive Engineers) based on converting to HFO-1234yf, and markets for chemical producers seeking to sell substitutes
appear to be continuing along this path. for refrigerants used in automobile air conditioning. Sec-
A large number of application patents have been filed tion IV of this paper looks at similar patents granted in
by transnational companies that could potentially impact India and China that could impact companies’ ability to
the use of HFO-1234yf in auto air conditioning. Many sell HFO-1234yf for use in auto air conditioning in these
large developing countries.
Box 1 shows that most of these same patents have
also been identified by Honeywell as applicable to
TABLE 1: Patents on the use of HFO-1234yf
use of HFO-1234yf in automobile air conditioning. As
in Automobile Air Conditioning described above, while other transnational companies
have patents on HFO and other blends for use in auto air
UNITED STATES EUROPEAN UNION JAPAN conditioning, the blend patents appear to be less relevant
US 7,279,451 EP 1 563 032 JP 4571183 and therefore are beyond the scope of this analysis.5
US 7,534,366 EP 1 716 216 JP 4699758
US 8,033,120 EP 1 725 628
US 8,065,882

2 Center for Climate and Energy Solutions

BOX 1: Honeywell Web Information on Patents for the Use of HFO-1234yf in Auto Air
Conditioning

SOLSTICE® YF PATENT INFORMATION

Following is a listing of the Honeywell patents under which certain limited rights are granted to purchasers of Honeywell’s
Solstice yf product. The patents under which rights are granted are limited by application and in accordance with the terms
of the purchased product’s label license.

For automotive air-conditioning applications:

For the US:
• US 8,065,882
• US 8,033,120
• US 7,279,451
• US 7,534,366
• US 9,157,017
For the EU:
• EP 1 563 032
• EP 1 725 628
For Japan:
• JP 4571183
Honeywell recently updated this web page to include one new patent in the United States (US 9,157,017) and one in
Europe (EP 1 563 032). It also eliminated one patent in Europe (EP 1 716 216) and one in Japan (JP 4699758) where legal
challenges have successfully revoked the patents with all appeals exhausted. See section III below.
Source: “Solstice® yf Patent Information | European Refrigerants,” Honywell, last accessed July 5, 2016, [Link]
solstice-yf-patent-information.

III. STATUS OF LEGAL CHALLENGES

This analysis focuses on the nine application patents avenues of appeal are exhausted, or the time for taking
identified in Table 1 that impact the use of HFO-1234yf an appeal has expired, patents remain in effect, notwith-
in automobile air conditioning and that have been the standing a determination that all claims are invalid.
subject of legal challenges. All of the relevant claims6 The reasoning behind the rejection of specific claims
included in these nine cases have been rejected by the in these patents varies but includes: a lack of novelty or
legal body responsible for hearing the challenges and inventiveness due to the existence of prior art.7 For the
these rejections have been upheld on the initial appeal. European patent challenges, the revocations have been
In two of these cases (EP 1 716 216 and JP 4699758), the based on failure to describe in the application a basis for
appeals process has been exhausted and decisions revok- the claims added by amendment after filing the applica-
ing the patents are final. In the remaining seven patents, tion (i.e., an added matter issue).
appeals are at various stages of the legal process and may The following sections briefly describe each patent
not be finally resolved for some time. Under the rules and the current stage of legal challenges to that patent.
governing U.S., European, and Japanese patents, until all Table 2 summarizes this information.

Status of Legal Challenges: Patents Related to the Use of HFO-1234yf in Auto Air Conditioning 3
US 7,534,366 (US ‘366) 2016, the patent holder filed a request for rehearing by
the PTAB. If the request for rehearing is denied, and if
This patent issued from an application filed on October
the examiner again rejects the claims, and the PTAB af-
27, 2003. It covers a heat-transfer composition for use in
firms the rejections, the PTAB decision may be appealed
an air-conditioning system that is comprised of generally
to the CAFC.
at least 50 percent by weight of HFO-1234yf and at least
one polyalkylene glycol lubricant. The patent was chal-
lenged and a reexamination initiated (#95/002,189) at US 8,065,882 (US ‘882)
the U.S. Patent and Trademark Office (USPTO), where This patent issued from an application filed on March
all claims were rejected by the examiner. This ruling was 26, 2009. It covers several methods relating to auto air
appealed to the Patent Trial & Appeals Board (PTAB) conditioning or cooling air, including a method of trans-
and a decision was handed down on March 20, 2016 ferring heat to or from a fluid or body to provide cooling
affirming the examiner’s decision to reject all claims. of air in an automobile with the specifics of the heat-
An appeal of the PTAB decision to the U.S. Court of Ap- transfer composition described by a chemical formula in
peals for the Federal Circuit (CAFC) was filed on May 2, the patent. This formula encompasses HFO-1234yf. All
2016 and is pending.8 claims in the patent were rejected or cancelled during a
USPTO reexamination (#95/002,030). On appeal, the
US 7,279,451 (US ’451) PTAB affirmed the rejection of the claims either on the
same grounds, or in some cases, on alternative grounds.
This patent issued from an application filed on April 29,
Because the PTAB asserted new grounds for some of the
2004. It covers a heat-transfer composition comprising at
rejected claims, the patent holder requested re-opening
least one fluoroalkene described by a chemical formula
prosecution before the examiner for consideration of
contained in the patent (which includes HFO-1234yf as
new evidence and arguments regarding the new grounds
a subset), and that makes up between 5 and 99 percent
of rejection. In addition, on May 2, 2016, the patent
by weight of the composition. A request to reexamine
holder filed a request for a rehearing before the PTAB. If
this patent was granted by the USPTO (#95/000,576)
the request for rehearing is denied, and if the examiner
resulting in the initial rejection of all pending claims
again finally rejects the claims and the PTAB affirms the
by the examiner. Upon appeal to the PTAB, the previ-
rejections, the PTAB decision may be appealed to the
ous decision rejecting all claims was affirmed. A request
CAFC.
for rehearing by the PTAB was filed on May 2, 2016 and
awaits a decision. If the request is denied, the PTAB deci-
sion may be appealed to the CAFC. EP 1 563 032 (EP ‘032)
This patent is derived from the European regional stage
US 8,033,120 (US ‘120) of a Patent Cooperation Treaty (PCT) application (pub-
lished as WO 2004/037913) with an international filing
This patent issued from an application filed on April
date of October 27, 2003. It covers the use as a heat-
20, 2009. It covers a method of cooling air comprising
transfer composition of a composition comprising at least
providing a heat-transfer fluid that includes a lubricant
one HFO-1234 and a polyol ester or polyalkylene glycol
and a fluoroalkene based on a chemical formula con-
lubricant. Opposition to this patent was filed in 2012 and
tained in the patent (that includes HFO-1234yf as one
the European Patent Office (EPO) Opposition Division
possible subset). The ‘120 Patent also was re-examined
issued a communication revoking the patent on January
(#95/001,783) and the examiner’s decision to reject all
15, 2015. An oral hearing is scheduled for January 17,
the claims was appealed to the PTAB. The PTAB deci-
2017 on an appeal of the revocation to the EPO Boards
sion affirmed the rejection of some of the claims by the
of Appeal filed by the patent holder.
re-examination examiner and rejected the remaining
claims on new grounds, substituting its own modified ba-
sis for rejection. Because the PTAB asserted new grounds EP 1 716 216 (EP ‘216)
for rejecting some of the claims, the patent holder This patent is derived from the European regional stage
requested re-opening prosecution before the examiner of a PCT application (published as WO 2005/105947)
for consideration of new evidence and arguments regard- filed on April 29, 2005. It covers use as a refrigerant of a
ing the new grounds of rejection. In addition, on May 2, composition comprising an HFO-1234 in an automobile

4 Center for Climate and Energy Solutions

air-conditioning system. The EPO Opposition Division tion (published as WO 2004/037913) filed on October
revoked this patent following a hearing. Following oral 27, 2003, and covers a heat-transfer composition compris-
proceedings, this decision was upheld on appeal by the ing a component described in a chemical formula in the
EPO Boards of Appeal and the time period for further patent along with a polyol ester or polyalkylene glycol
appeal has lapsed. lubricant. This patent has been ruled invalid based on
a decision by the Japan Patent Office (JPO) Board of
EP 1 725 628 (EP ‘628) Appeals. A further appeal to the high court affirmed the
This patent is a European regional stage of a PCT appli- invalidity decision and no further appeals are possible.
cation (published as WO 2005/042663) with an interna-
tional filing date of October 25, 2004. It covers a liquid JP 4571183 (JP ‘183)
composition for use in a compression refrigeration, air- This patent is a Japanese national stage of a PCT appli-
conditioning or heat-pump system comprising a general cation (published as WO 2005/105947) filed on April
formula including at least HFO-1234yf and a polyol ester 29, 2005, and covers use as a refrigerant of a constituent
or polyalkylene glycol lubricant. Several oppositions to containing tetrafluoropropane (HFO-1234) in air-condi-
this patent were filed in 2012–2013 and the EPO Opposi- tioner of an automobile. The patent has been ruled to be
tion Division issued a communication revoking the pat- invalid based on a decision by the JPO Board of Appeals,
ent on Jan. 15, 2015. An appeal of the revocation to the but a decision on appeal before the high court is pend-
Boards of Appeal has been filed by the patent holder. ing.

JP 4699758 (JP ‘758) SUMMARY OF LEGAL CHALLENGES

This patent is a Japanese national stage of a PCT applica- Table 2 summarizes the evolution and current status

TABLE 2: Summary of Legal Challenges

PATENT
NUMBER INITIAL APPEAL FURTHER APPEALS CURRENT STATUS
US ‘366 PTO re-examination— PTAB affirmed rejections Appealed to U.S. Court of Appeals
all claims rejected
US ‘451 PTO re-examination— PTAB affirmed rejections Rehearing by PTAB requested
all claims rejected
US ‘120 PTO re-examination— PTAB affirmed rejections; Rehearing by PTAB requested;
all claims rejected issued new rejections prosecution re-opened
US ‘882 PTO re-examination— PTAB affirmed rejections; Rehearing by PTAB requested;
all claims rejected issued new rejections prosecution re-opened
EP ‘032 EPO Opposition Divi- Under appeal to EPO Boards of Appeal Appeal of revocation is pending
sion revoked patent
EP ‘216 EPO Opposition Divi- EPO Boards of Appeal upheld revocation No further appeals possible
sion revoked patent
EP ‘628 EPO Opposition Divi- Under appeal to EPO Boards of Appeal Appeal of revocation is pending
sion revoked patent
JP ‘758 JPO Board of Appeals Appeals court affirmed invalidation Revocation is final
invalidated patent
JP ‘183 JPO Board of Appeals Under appeal to high court pending Appeal pending
invalidated patent

Status of Legal Challenges: Patents Related to the Use of HFO-1234yf in Auto Air Conditioning 5
of legal challenges to the nine key application patents one petition seeking inter parties review. The outcome of
examined in this analysis. It shows that in all nine cases, these challenges and any subsequent appeals regarding
the entire relevant set of claims contained in these this patent will be relevant to the use of HFO-1234yf in
patents has been rejected. In two of these cases, appeals auto air conditioning in the United States.10
have been exhausted and decisions are final. In the other A communication from the EPO issued recently stat-
seven, appeals are pending, requests for rehearing are ing its intention to grant a patent, EP 2314654 (divisional
awaiting a decision, or reconsideration of certain claims of EP’ 032) claiming a refrigerant composition compris-
by the initial examining authority is in progress. ing at least 50 percent by weight of a fluoroalkene having
a general formula that includes HFO-1234yf and a lubri-
ADDITIONAL PATENTS OF RELEVANCE cant which is a polyalkylene glycol.
A communication from the EPO issued in April
There are several other patents related to the use of
2016 stated its intention to grant a patent, EP 2277970
HFO-1234yf in auto air conditioning that recently
(divisional of EP’ 628) claiming, in pertinent part, a
have been issued and therefore have not yet resulted in liquid composition for use in compression refrigeration,
legal challenges. In particular, in the United States, US air-conditioning and heat pump systems comprising a
9,157,017 issued from an application filed on March 26, fluoroalkene containing from 3 to 4 carbon atoms and
2014.9 It claims a method for cooling air in an automo- at least one but not more than two double bonds and a
bile using HFO-1234yf and a polyalkylene glycol lubri- lubricant, wherein the mixture has one liquid phase with
cant. This patent is at the early stages of being chal- at least one temperature in the range between -40°C and
lenged by two petitions seeking post grant review and 70°C.11

IV. PATENTS IN INDIA AND CHINA RELEVANT TO USING HFO-1234YF IN

AUTO AIR CONDITIONING
Given the potentially substantial markets in India and fied as they go through national review in a particular
China for the use of a substitute refrigerant in auto country, this section looks at each of the claims con-
air-conditioning systems, it is not surprising that applica- tained in two patents granted in India and one in China
tions for patents have been filed for this technology in that appear most relevant to the use of HFO-1234yf in
these countries. It is also not surprising that the patents automobile air conditioning. The analysis presented here
filed in both countries share many common elements examines each of the claims in these three patents and
with patents filed in the United States, Europe, and compares them to claims included in eight of the nine
Japan given that they arise from the same PCT applica- challenged patents (from the United States, Europe, and
tion. In fact, the PCT was created in part to make it Japan) previously discussed. The objective of this analysis
easier to file the same patent application in multiple is to see if the subject matter of each of the claims in the
national or regional jurisdictions. While the applications Indian and Chinese patents can be matched with the
leading to these patents start off the process virtually same or closely similar subject matter of claims that have
the same (i.e., filed under the PCT), as they are reviewed been challenged and rejected (pending review) in one
and acted upon by national or regional patent offices, or more of the eight relevant patents from the United
the individual claims can be modified, for example, to States, European Patent Convention, or Japan.
address objections raised by specific patent offices and It is important to note that decisions rejecting claims
to take into account differences in local or regional legal by one national patent authority are not in any way bind-
practices.12 Nonetheless, it is significant that the relevant ing on another jurisdiction. Each country’s patent office
patents in India and China contain the same or similar makes its own determinations based on national laws.
claims to those found in related patents in the United For example, the test applied in Europe to assess whether
States, Europe, and Japan. a claim formally finds basis in the application as origi-
Because claims in specific patents are often modi- nally filed is very strict and this same test is not applied in

6 Center for Climate and Energy Solutions

any other jurisdiction. Nonetheless, there is considerable example, IN 239049 contains many of the same claims or
commonality across nations in patent laws developed to claims similar subject matter as recited in the claims of
comply with the Patent Cooperation Treaty and the same the closely related US ‘120 and US ‘451 patents. All the
information used to challenge the novelty or inventive- claims in both of these U.S. patents have been rejected
ness of claimed subject matter in one national jurisdic- during reexamination and the decisions affirmed by the
tion may be introduced in proceedings in other national PTAB. Requests for a rehearing of the appeal decision by
jurisdictions. the PTAB or a reopening of the proceeding have been
filed by the patent holder. The subject matter of key
KEY FINDINGS FROM COMPARISONS claims in the Indian patent also tracks closely the subject
For every one of the claims in the two Indian and one matter of key claims in the European and Japanese
Chinese patents, we found the same or substantially simi- patents that have been rejected with appeals pending in
lar subject matter in claims that had been rejected in one some cases.
or more of the eight U.S., European, or Japanese patents
The claims in the IN 250569 patent are laid out in
examined in this analysis. Attachments 1 and 2 list the
Attachment 2 and are also compared to the same eight
claims in the two Indian patents in the first column and
relevant patents from the United States, Europe, and
identify corresponding claims from eight patents in oth-
Japan. In this case, all 48 claims in the Indian patent
er jurisdictions (United States, Europe, and Japan) that
closely match rejected claims from the US ’882 patent.
have been rejected. Since some of the decisions rejecting
claims are under appeal, as stated above, the information In addition, a large number of the claims in the Indian
contained in these tables could change over time. Attach- patent correspond to subject matter recited in claims
ment 3 does the same cross-comparison for the Chinese that have been rejected in other of the patents including
patent believed to be most relevant. those from Europe and Japan presented in the table.
The two patents granted in India that appear to There are pending oppositions against IN 239049 and
be most relevant to the use of HFO-1234yf in auto air IN 250569, but the status of that proceeding is undeter-
conditioning have been filed by Honeywell and are: IN mined at this time.13
250569 (Compositions Containing Fluorine Substituted The most relevant Chinese patent CN 1732243 (CN
Olefins) and IN 239049 (Heat-Transfer Composition ‘243) is also held by Honeywell and covers the use of a
for an Air-Conditioning System). The IN 250569 patent heat-transfer composition in an automobile air-condi-
focuses on a “method of transferring heat to or from a tioning system and apparatus, said heat-transfer composi-
body to provide cooling of air in an automobile” using a
tion comprising a refrigerant comprising HFO-1234yf
heat-transfer composition defined by a chemical for-
in an amount of at least 50 percent by weight and a
mula which includes HFO-1234yf. The IN 239049 patent
lubricant selected from polyalkylene glycol and/or polyol
focuses on “a heat-transfer composition for use in an air-
esters.14 It is a national stage of the PCT application (pub-
conditioning system” with specifications that include the
lished as WO 2004/037913) which claims a priority date
use of HFO-1234yf of at least 50 percent by weight.
of October 25, 2002, to the same two U.S. provisional
For IN 239049, we found that its 18 claims closely
applications from which the US ‘366 claims priority.
matched specific claims contained in the US ‘366 patent.
Attachment 3 compares the claims related to the use
In the case of all 18 claims we found that the exact or
similar claim in the US ‘366 patent has been rejected in of HFO-1234yf in auto air conditioning in the Chinese
the reexamination conducted by the USPTO. On appeal patent to the claims contained in the eight U.S., E.U. and
to the PTAB, the rejection of all claims was affirmed and Japanese patents.15 It shows that for the subset of claims
a further appeal to the CAFC is pending. Attachment in CN ‘243 relevant to HFO-1234yf and automobile air
1 identifies specific claims in the US ’366 patent that conditioning that similar subject matter is recited in the
match each of the claims in the Indian patent. rejected claims of US ‘366. The attachment also shows
Attachment 1 goes on to show that the subject matter that the subject matter or subsets of the subject matter
of claims in IN 239049 was also contained in exact or of relevant claims in CN ‘243 can be found in many of
similar form in a number of the other seven relevant pat- the rejected claims contained in the other seven patents
ents granted in the United States, Europe, and Japan. For examined in this analysis.

Status of Legal Challenges: Patents Related to the Use of HFO-1234yf in Auto Air Conditioning 7
 V. EXPIRATION DATES FOR RELEVANT PATENTS
To the extent patents survive the legal challenges tions expire 20 years from the filing date of the earliest
described above, they will continue to restrict the uses previously claimed priority application (with provisional
of the surviving claimed subject matter in the jurisdic- patents excluded). For patents arising from regional or
tions in which they have been granted until they reach national stage Patent Cooperation Treaty applications,
their expiration dates. In general, the patents relevant to the effective filing date is the date of the PCT filing.
this topic expire 20 years after the effective filing date. Table 3 provides the relevant priority claims, dates and
Determining the “effective filing date”, i.e., when the expiration dates for the patents examined in this analysis
20-year period begins, is of critical importance. Many relevant to the use of HFO-1234yf in automobiles. It
of the patents discussed above are related and all claim shows that for the patents examined in this analysis, the
priority from previously filed applications. In the United relevant expiration dates range from 2023–25.
States, patents that claim priority from earlier applica-

VI. CONCLUSIONS
This analysis looked at the current status of legal chal- makes its own legal determinations, our analysis demon-
lenges to those application patents that appear most strates that the claims contained in these relevant patents
relevant to the use of HFO-1234yf in auto air condition- in India and China closely match the subject matter of
ing. It focused on nine patents in the United States, specific rejected claims in one or more of the eight U.S.,
the European Patent Convention, and Japan; each one European, or Japanese patents we reviewed.
has been successfully challenged with all of its relevant The evidence to date shows a strong record of suc-
claims rejected. However, any conclusions based on these cessful challenges revoking patents restricting the use
outcomes must be viewed as tentative because appeals of HFO-134yf in automobile air conditioning. However,
are pending in seven of the nine cases, one additional given the time required for appeals to play out and the
patent in the United States is in the early stages of chal- ability to file new divisional applications, it is difficult to
lenge, and additional patents (i.e., divisionals) are likely predict a timetable for when it may be possible for chemi-
to issue from applications currently in the pipeline or cal producers to sell in key markets unrestricted by pat-
could potentially emerge at some future date. ents. Based on the patents reviewed in this analysis, one
Patents on the use of HFO-1234yf in automobile air clear end point is the expiration of relevant application
conditioning also have been granted in India and China. patents that occurs in the 2023–25 timeframe. Whether
These patents are part of the same families as those that patent restrictions are lifted before then will be deter-
have been successfully challenged16 in the U.S., Europe- mined by the outcomes of the on-going legal challenges.
an, and Japanese Patent Offices. While each jurisdictions

8 Center for Climate and Energy Solutions

TABLE 3: Relevant Dates for Some Key Patents and Applications Relating to HFO-1234yf

PATENT OR EARLIEST CLAIMED PRIORITY EARLIEST CLAIMED EFFECTIVE EXPIRATION

APPLICATION NO. DOCUMENT NOS. PRIORITY DATES FILING DATE DATE
US 7,279,451 60/421,435 10/25/2002​ 10/27/2003 10/27/2023
60/421,263 10/25/2002​
10/694,272 10/27/2003​
10/694,272 10/27/2003​
10/695,212 10/27/2003
US 7,534,366 60/421,435 10/25/2002​ 10/27/2003 10/27/2023
60/421,263 10/25/2002

US 8,033,120 60/421,263 10/25/2002​ 10/27/2003 10/27/2023

60/421,435 10/25/2002​
10/694,273 10/27/2003
US 8,065,882 60/421,263 10/25/2002​ 10/27/2003 10/27/2023
60/421,435 10/25/2002​
10/694,272 10/27/2003​
10/694,272 10/27/2003
US 9,157,017 60/421,263 10/25/2002​ 10/27/2003 10/27/2023
10/694,272 10/27/2003
EP 1 563 032 US 60/421,262 10/25/2002​ 10/27/2003 10/27/2023
US 60/421,435 10/25/2002​
PCT/US2003/033874 10/27/2003
EP 1 716 216 US 10/837,525 4/29/2004​ 4/29/2005 4/29/2025
PCT/US2005/014873 4/29/2005 (N/R, as this
patent has
been finally
revoked)
EP 1 725 628 US 10/695,212 10/27/2003​ 10/25/2004 10/25/2024
PCT/US2004/035132 10/25/2004
JP 4571183 US 10/837,525 4/29/2004​ 4/29/2005 4/29/2025
PCT/US2005/014873 4/29/2005
JP 4699758 US 60/421,262 10/25/2002​ 10/27/2003 10/27/2023
US 60/421,435 10/25/2002​
PCT/US2003/033874 10/27/2003
CN Pub. # 1732243 US 60/421,262 10/25/2002​ 10/27/2003 10/27/2023
App. # 200380107462 US 60/421,435 10/25/2002​
PCT/US2003/033874 10/27/2003
IN 250569 US 10/837,525 4/29/2004​ 4/29/2005 4/29/2025
PCT/US2005/014873 4/29/2005
IN 239049 US 60/421,262 10/25/2002​ 10/27/2003 10/27/2023
US 60/421,435 10/25/2002​
PCT/US2003/033874 10/27/2003

Status of Legal Challenges: Patents Related to the Use of HFO-1234yf in Auto Air Conditioning 9
10
APPENDIX
Attachment 1: Indian 239049

INDIA 239049: HEAT-TRANSFER

COMPOSITION FOR AN AIR-CONDI-
TIONING SYSTEM US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
Status Rejected Rejected Rejected Rejected Rejected Rejected Rejected Rejected
claims from claims from claims from claims from claims from claims from from JP from JP
US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 469975817 4571183

Center for Climate and Energy Solutions

(PTAB (Request (Request (Request (on appeal) (final) (final) (on appeal)
decision for rehear- for rehear- for rehear-
appealed to ing of PTAB ing of PTAB ing of PTAB
Federal Cir- decision decision decision
cuit on May filed May 2, filed May 2, filed May 2,
3, 2016) 2016) 2016) 2016)
1. A heat-transfer composition for use Cl. 1 Cl. 4 Claims Cl. 10, in a Cls. 1+2+ Cls. 1+6+7, Cls. Cl.s 1+4+5,
in an air-conditioning system compris- regarding are to a method for 8+ 9, and but at least 1+2+5+8. but excludes
ing: HFO-1234yf method of cooling air. 12(i)+13+17. 50% by wt. no toxicity
and cl. 22 transferring in a range in and 50% by
(a) at least 50% by weight of regarding heat that cl. 2 or 3. wt.
2,3,3,3-tetrafluoropropene (HFO- 50% by wt. includes a
1234yf) having no substantial acute fluoroalkene
toxicity; and and a lubri-
(b) at least one poly alkylene glycol cant; cl. 7
lubricant. is specific
to HFO-
1234yf, cl.
22 to 50%
by wt.; cl.
14 to poly-
alkylene
glycol.
2. The composition of claim 1 having Cl. 2 Cl. 16 Cl. 16 NA NA NA NA NA
a Global Warming Potential (GWP) of
not greater than 150.
 INDIA 239049: HEAT-TRANSFER
COMPOSITION FOR AN AIR-CONDI-
TIONING SYSTEM US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
3. The heat-transfer composition of Cl. 3 Cl. 13 NA NA NA NA NA NA
claim 1 optionally comprising at least
one compatablizer.
4. The heat-transfer composition of Cl. 4 Cl. 8, but in Cl. 12, but Cls. 4 and Cl. 5, but in Cl. 4, but in Cl. 3, but in
claim 1 wherein said lubricant is pres- a range of in a range of 15, but in a range of a range of a range of
ent in an amount of at least 30% by 30–50% 30–50% a range of 30–50% 30–50% 30–50%
weight. 30–50%
5. The composition of claim 1 Cl. 7 Cl. 8, but in Cl. 12, but Cl. 11 Cls. 4 and Cl. 5, but in Cl. 4, but in Cl. 3, but in
wherein said lubricant is present in a range of in a range of 15, but in a range of a range of a range of
an amount of 50% by weight of the 30–50% 30–50% a range of 30–50% 30-–0% 30–50%
composition. 30–50%
6. The composition of claim 1 where- Cl. 8 NA NA NA NA NA NA NA
in said composition is non-flammable.
7. The composition of claim 1 having Cl. 9 NA NA NA NA NA NA NA
a Global Warming Potential (GWP) of
not greater than 100.
8. The composition of claim 1 having Cl. 10 Cl. 17 Cl. 17. Cls. 1 and NA NA NA NA
a Global Warming Potential (GWP) of 13 recite
not greater than 75. GWP not
greater than
75
9. The composition of claim 1 having Cl. 11 Cl. 19 Cl. 19 NA NA NA NA NA
an Ozone Depletion Potential (ODP)
of not greater than 0.02.
10. The composition of claim 1 Cl. 12 Cl. 23 Cl. 23 NA Cls. 3+8 NA Cls. 3+8 NA
wherein said HFO-1234yf comprises and 12+14
at least 70% by weight of the compo-
sition.
11. The composition of claim 10 Cl. 13 NA NA NA NA NA NA NA
wherein said compatablizer is
selected from the group consisting

Status of Legal Challenges: Patents Related to the Use of HFO-1234yf in Auto Air Conditioning
of propane, butane, pentane, and
combinations of these.

11
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INDIA 239049: HEAT-TRANSFER
COMPOSITION FOR AN AIR-CONDI-
TIONING SYSTEM US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
12. The composition of claim 10 Cl. 14 Cl. 36 NA NA NA NA NA NA
comprising compatablizer in amounts
of from 0.5 to 5 percent by weight of
the composition.
13. The composition of claim 1 having Cl. 15 NA Cls. 35, 44 Cl. 13 NA NA NA NA
a capacity relative to HFC-134a of 1.
14. The composition of claim 1 having Cl. 16 NA Cls. 35, 44 Cl. 13 NA NA NA NA
a Coefficient of Performance (COP)

Center for Climate and Energy Solutions

relative to HFC-134a of 1.
15. The composition of claim 1 Cl. 18 Cl. 33 NA NA NA NA NA NA
further comprising a surfactant and a
solubilizing agent.
16. The composition of claim 1 Cl. 19 Cl. 9 in part Cls. 13, 41 NA Cl. 6, 19 NA Cl. 1 in part NA
wherein said lubricant optionally in part
comprises at least one polyol ester.
17. The composition of claim 1 Cl. 21 Cl. 30 Cls. 30, 35, Cls. 1 and NA NA NA NA
wherein said composition has one liq- 44, 51 14, but for a
uid phase at at least one temperature broader set
between -50°C and +70°C. of refriger-
ants of
which HFO-
1234yf is a
subset.
18. The composition of claim 1 Cl. 23 Cls. 6+7 Cls. 11, 39 Cl. 10, but Cls. 8 and Cl. 7, but Cl. 8, Cl. 5,
wherein said fluorinated propene the term 17, but with with the but with but with
consists essentially of HFO-1234yf “consisting the word word “com- the word the word
and lubricant. essentially “compris- prising” “contains” “contains”
of” is re- ing” instead instead of instead of instead of
placed with of “consist- “consist-ing “consisting “consisting
“compris- ing essen- essentially essentially essentially
ing.” tially of.” of.” of.” of.”
 Attachment 2: Indian 250569

INDIA 250569: COMPOSITION

CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
Status Rejected Rejected Rejected Rejected Rejected Rejected Rejected Rejected
claims from claims from claims from claims from claims from claims claims claims
US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 from EP from JP from JP
1716216 469975818 4571183
(PTAB (Request (Request for (Request (on appeal)
decision for rehear- rehearing of for rehear- (final) (final) (on ap-
appealed to ing of PTAB PTAB deci- ing of PTAB peal)
Federal Cir- decision filed sion filed decision filed
cuit on May May 2, 2016) May 2, 2016) May 2, 2016)
3, 2016)

Status of Legal Challenges: Patents Related to the Use of HFO-1234yf in Auto Air Conditioning
13
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INDIA 250569: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
1. A method of transferring heat to Cl. 1 is much Cl. 1 of the Cl. 1 is Cls. 1 and 14 Cl. 1 is Cl. 1 is Cl. 1 is Cl. 1 is
or from a fluid or body to provide narrower ‘451 Patent is almost iden- of the ‘120 similar in that similar similar, similar
cooling of air in an automobile, said than cl. 1 to a heat- tical except are broader it recites the in that it in that it in that it
method comprising: of the ‘569 transfer com- that four as to the use of HFO- recites recites recites
Indian Patent position that halogens are method and 1234 (which the use of a heat- the use of
(a) providing a heat-transfer system but similar is similar to, required in- the recita- is a subset of HFO-1234 transfer HFO-1234
comprising an automobile air-condi- in that it but broader stead of four tion of the the structure (which is constituent (which is
tioning system; recites HFO- than, the Fluorines. fluoroalkene; in cl. 1 of the a subset of having the a subset of
(b) providing in said system a heat- 1234yf as a fluoroalkene Formula ‘569 Indian the struc- formula as the struc-

Center for Climate and Energy Solutions

transfer composition comprising at heat-transfer recited in the (II) in the Patent) and ture in cl. 1 shown in ture in cl. 1
least one lubricant such as herein composition ‘569 Indian Indian Patent select lubri- of the ‘569 cl. 1 of the of the ‘569
described and at least one fluoro- together with Patent. The is a subset of cants; cl. 9 Indian Pat- ‘569 Indian Indian Pat-
alkene having a total of at least four a specific ‘451 claim Formula (I) in recites use in ent) in an Patent and ent) in an
fluorine substituents, said fluoro- lubricant of 1 does not the ‘120. air condition- automobile at least one automobile
alkene being of Formula II: a specific require a ing. air-con- of a select air-con-
R R viscosity. lubricant or ditioning group of ditioning
4 Fs, and system. lubricants. system.
C C R’
does require
R a GWP ≤
where 1000. How-
ever, 4 Fs or
R’ is (CR 2)nY,
a lubricant
Y is CF3, are required
in later
each R is independently F or H, claims of the
‘451.
and n is 0 or 1,

provided that there is at least one H

on said unsaturated terminal carbon
and wherein said fluoroalkene has
no substantial toxicity.
 INDIA 250569: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
2. The method as claimed in claim NA Cl. 1 (500 Cl. 16 GWP Cl. 1 recites NA Cl. 9 NA NA
1 wherein said composition has a GWP is ≤ not greater GWP not
Global Warming Potential (GWP) of 1000, as re- than 150; cl. greater than
not greater than 500. cited in ‘451’s 17 GWP not 75; cl. 14
cl. 1) greater than recites GWP
75 not greater
than 150.
3. The method as claimed in claim 2 Cl. 1 Cl. 4 Cl. 7 Cl. 10 Cls. 8 and 17 Cl. 7 Cl. 8 Cl. 5
wherein said fluoroalkene of Formula
II comprises 1,1,1,2-tetrafluoropro-
pene (HFO-1234yf).
4. The method as claimed in claim 1 NA NA NA NA NA NA NA NA
wherein said providing step com-
prises circulating said composition
in said automobile air-conditioning
system.
5. The method as claimed in claim NA This would Cl. 2 Cl. 2 NA NA NA NA
1 wherein said unsaturated terminal not be HFO-
carbon has one F substituent. 1234yf.
6. The method as claimed in claim 1 Since Cl. 1 is Cl. 2 Cl. 3 NA Inherently in Inherently Cl. 1 and Inherently
wherein n is 0. directed to cls. 8 and 17, in cl. 7, inherently in cl. 5,
HFO-1234yf, directed to directed in cl. 8, directed
n is inher- HFO-1234yf. to HFO- directed to HFO-
ently 0. 1234yf. to HFO- 1234yf.
1234yf.

Status of Legal Challenges: Patents Related to the Use of HFO-1234yf in Auto Air Conditioning
15
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INDIA 250569: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
7. The method as claimed in claim Since Cl. 1 is Cls. 4, 6; this Cl. 4 Cl. 5, but Since Cls. 8 Since Cl. 7 Since Cl. 8 Since Cl. 5
4 wherein said unsaturated terminal directed to structure is stated as and 17 are is directed is directed is directed
carbon has no F substituent. HFO-1234yf, inherent in both substit- directed to to HFO- to HFO- to HFO-
there is in- HFO-1234yf. uents on this HFO-1234yf, 1234yf, 1234yf, 1234yf,
herently no F carbon being there is in- there is there is there is
in unsaturat- H – hence herently no F inherently inherently inherently
ed terminal no F substitu- in unsaturat- no F in un- no F in un- no F in un-
carbon ents. ed terminal saturated saturated saturated
carbon terminal terminal terminal

Center for Climate and Energy Solutions

carbon. carbon. carbon.
8. The method as claimed in claim Yes, since Cl. Cl. 4, 6. Cl. 5 Cls. 5, 17 Yes, since cls. Yes, since Yes, since Yes, since
1 wherein each substituent on the 1 is directed 8 and 17 are cl. 7 is cl. 8 is cl. 5 is
unsaturated terminal carbon is H. to HFO- This structure directed to directed directed directed
1234yf. is inherent in HFO-1234yf. to HFO- to HFO- to HFO-
HFO-1234yf. 1234yf. 1234yf. 1234yf.
9. The method as claimed in claim 1 NA Cl. 3, but this Cl. 6 NA NA NA NA NA
wherein n is 1. would not be
a propene.
10. The method as claimed in Cl. 1 Cl. 6 Cl. 7, Cl. 10 Cls. 8 and Cl. 7, Cl. 8, Cl. 5,
claim 1 wherein said fluoroalkene except for 17, except except for except for except for
of Formula II consists essentially of the words for the words the words the words the words
1,1,1,2-tetrafluoropropene (HFO- “compris- “comprising.” “compris- “contains.” “contains.”
1234yf). ing” in cl. ing.”
7 instead of
“consisting
essentially
of” in cl. 10
of the Indian
Patent; and
the same in
cls. 11 and
39.
 INDIA 250569: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
11. The method as claimed in claim NA NA Cl. 8 Cls. 8, 20 Cls. 7, 12, 16. NA Cl. 7 NA
1 wherein said fluoroalkene of For-
mula II comprises 1,1,1,3-tetrafluoro-
propene (HFO-1234ze).
12. The method as claimed in claim NA NA Cl. 9 Cls. 8, 20 NA NA NA NA
1 wherein said fluoroalkene of For-
mula II comprises trans 1,1,1,3-tetra-
fluoropropene (HFO-1234ze).
13. The method as claimed in claim NA The heat- Cl. 10 (iden- Cls. 7 and 19 NA Cl. 2, but NA NA
1 comprising conditioning the air in transfer tical), and for com- for use of
an automobile comprising: fluid recited cls. 33, 47, pressor and HFO-1234
in cl. 13 is and 50 with condenser
(a) providing a vapor compression similar to the regard to the and tempera-
air-conditioning system having at heat-transfer wt.% HFO- ture, but not
least one compressor, at least one composition 1234yf. HFO-1234yf
condenser and a heat-transfer fluid of cl. 4 of the or wt.%
in said system, said heat-transfer fluid ‘451 Patent.
comprising 1,1,1,2-tetrafluoropropene The ‘451 has
(HFO-1234yf) in an amount of from no compo-
5 % by weight to 99 % by weight of nent or temp.
the heat-transfer fluid; and require-
(b) operating said condenser in a ments.
temperature range that includes
150°F.
14. The method as claimed in claim NA Cl. 14 of the Cl. 21 as cl. Cl. 10 for NA Cl. 3, but NA NA
11 wherein said heat-transfer compo- Indian pat- 1 relates to HFO-1234yf for use of
sition comprises from 5% by weight ent recites a cl. 8 (HFO- but no wt. % HFO-1234.
to 95% by weight of 1,1,1.2-tetrafluo- blend (Read 1234ze) limitation.
ropropene (HFO-1234yf). with claim
11), but the
stated % if yf
is recited in

Status of Legal Challenges: Patents Related to the Use of HFO-1234yf in Auto Air Conditioning
cl. 21 of the
‘451 Patent.

17
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INDIA 250569: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
15. The method as claimed in claim Cl. 17 Cls. 7 and 8 Cl. 12 Cls. 9, 11, 21 Cl. 4 Cl. 5 Cl. 4 Cl. 3
13 wherein said lubricant is present
in the composition in an amount of
from 30% to 50% by weight of the
heat-transfer composition based on
the total weight of said lubricant and
said compound(s) of Formula II.
16. The method as claimed in claim Cl. 1 recites Cl. 9 Was the NA Cls. 1 and Cl. 6 Cl. 1 re- Cl. 4
1 wherein said lubricant is selected polyalkylene same as orig- 12 recite recites cites polyol recites

Center for Climate and Energy Solutions

from the group consisting of polyol glycol lubri- inal cl. 13, polyol ester polyalkyl- ester and polyalkyl-
esters, polyalkylene glycols, polyal- cant which was and polyal- ene glycol polyalkyl- ene glycol
kylene silicon oils, mineral oils, alkyl canceled in kylene glycol lubricants. ene glycol lubricants.
benzenes, poly(alpha-olefins) and re-exam lubricants; lubricants;
combinations of these. cls. 5 and cl. 5 recites
18 recites polyalkyl-
polyalkylene ene glycol
glycol and and cl.
cls. 6 and 6 recites
19 recites polyol
polyol ester ester lubri-
lubricants. cants.
17. The method as claimed in claim Cl. 1 Recites a Cl. 14, as cl. Cls. 10, 12 Cls. 1, 5, 12, Cl. 6 Cls. 1, 5 Cl. 4
11 wherein said lubricant comprises blend (read 1 relates to and 18 ex- except
at least one polyalkylene glycol. with claim cl. 8, HFO- cept for the for the “at
11), but this 1234ze “at least one” least one”
lubricant is in language. language.
cl. 10 of the
‘451 Patent.
18. The method as claimed in claim Cl. 1 Cl. 11 Cl. 14 NA Cls. 1, 5, 12, Cl. 6 Cls. 1, 5 Cl. 4
1 wherein said lubricant comprises and 18 ex- except
polyalkylene glycol ester. cept for the for the “at
“at least one” least one”
language. language.
 INDIA 250569: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
19. The method as claimed in claim Cl. 2 Cl. 16 Cl. 16 Cl. 14 NA NA NA NA
1 wherein said heat-transfer compo-
sition has a Global Warming Poten-
tial (GWP) of not greater than 150.
20. The method as claimed in claim Cl. 10 Cl. 17 Cl. 17, 52 Cl. 1 NA NA NA NA
1 wherein said heat-transfer compo-
sition has a Global Warming Poten-
tial (GWP) of not greater than 75.
21. The method as claimed in claim NA Cl. 18 Was the NA NA NA NA NA
1 wherein said heat-transfer compo- same as
sition has an ozone depletion poten- original cl.
tial (ODP) of not greater than 0.05. 18, which
was can-
celed during
re-exam.
22. The method as claimed in claim Cl. 11 Cl. 19 Was the NA NA NA NA NA
1 wherein said heat-transfer compo- same as
sition has an ozone depletion poten- original cl.
tial (ODP) of not greater than 0.02. 19, which
was can-
celed during
re-exam.
23. The method as claimed in claim NA Cl. 20 Was the NA NA NA NA NA
1 wherein said heat-transfer compo- same as
sition has an ozone depletion poten- original cl.
tial (ODP) of not greater than zero. 20, which
was can-
celed during
re-exam.
24. The method as claimed in claim NA Cl. 21 Cls. 21, 38 NA NA Cl. 3 for NA NA
1 wherein said compound of For- HFO-1234
mula II is present in the composition

Status of Legal Challenges: Patents Related to the Use of HFO-1234yf in Auto Air Conditioning
in an amount of from 5 % by weight
to 95 % by weight.

19
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INDIA 250569: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
25. The method as claimed in claim Cl. 1 Cl. 22 Cl. 22 NA Cls. 2, 13 NA Cl. 2 NA
1 wherein said compound of For-
mula II is present in the composition
in an amount of at least 50 % by
weight.
26. The method as claimed in NA Cl. 23 Cls. 23, 45 NA Cls. 3, 14 NA Cl. 3 NA
claim 1 wherein said compound of
Formula II is present in the composi-
tion in an amount of at least 70 % by

Center for Climate and Energy Solutions

weight.
27. The method as claimed in claim NA Cl. 24 Cls. 24, 46 NA NA NA NA NA
1 wherein said heat-transfer compo-
sition comprises one or more of the
following: difluoromethane (HFC-32);

pentafluoroethane (HFC-125);

1,1,2,2-tetrafluoroethane (HFC-134);
1,1,1,2-tetrafluoroethane (HFC-134a);
difluoroethane (HFC-152a);

1,1,1,2,3,3,3-heptafluoropropane
(HFC-227ea); 1,1,1,3,3,3-hexafluoro-
propane (HFC-236fa);

1,1,1,3,3-pentafluoropropane (HFC-
245fa); 1,1,1,3,3-pentafluorobutane
(HFC-365mfc); water; and CO2.
28. The method as claimed in claim NA Cl. 25 Cl. 25 NA NA NA NA NA
1 wherein said heat-transfer com-
position comprises a flammability
suppressant.
 INDIA 250569: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
29. The method as claimed in claim NA Cl. 26 Was the NA NA NA NA NA
28 wherein said flammability sup- same as
pressant comprises CF3I. original cl.
26, which
was can-
celed during
re-exam.
30. The method as claimed in claim NA Cl. 27 Was the NA NA NA NA NA
1 wherein said lubricant comprises same as
an alkyl benzene. original cl.
27, which
was can-
celed during
re-exam, and
is the same
as part of
cls. 41, 49,
and 51.
31. The method as claimed in claim NA Cl. 28 Cl. 28 NA NA NA NA NA
1 wherein said lubricant comprises
an ester oil.
32. The method as claimed in claim NA Cl. 29 Was the NA NA NA NA NA
1 wherein said lubricant comprises a same as
poly(alpha-olefin) oil. original cl.
29, which
was can-
celed during
re-exam; and
is the same
as part of
cls. 41, 49,
and 51.

Status of Legal Challenges: Patents Related to the Use of HFO-1234yf in Auto Air Conditioning
21
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INDIA 250569: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
33. The method as claimed in claim Cl. 21 Cl. 30 Cl. 30, and Temp. range NA NA NA NA
1 wherein said heat-transfer compo- part of cls. concept is in
sition has one liquid phase at at least 35, 44, and cl. 1
one temperature between -50°C and new re-exam
+70°C. cl. 81.

34. The method as claimed in claim NA Cl. 31 Cl. 31 NA NA NA NA NA

1 wherein said heat-transfer compo-

Center for Climate and Energy Solutions

sition is stable when in contact with
aluminum, steel and copper under
the conditions of use in said air-con-
ditioning systems.
35. The method as claimed in claim NA NA Cl. 33 except Cls. 7 and 19 NA NA NA NA
1 wherein said automobile air-con- for temp. in part
ditioning system comprises a vapor require-
compression air-conditioning system ment, but
having at least one compressor and also in cl. 47
at least one condenser operable in with temp.
a temperature range that includes requirement;
150°F. and in new
re-exam cl.
86.
 INDIA 250569: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
36. The method as claimed in claim NA The heat- Cl. 50 NA NA NA NA NA
1 wherein said automobile air-condi- transfer fluid
tioning system includes at least one of cl. 36 of
compressor and at least one evapo- the Indian
rator, said method comprising: Patent is
similar to the
(a) utilizing in said system a heat- heat-transfer
transfer fluid comprising 1,1,1,2- composition
tetrafluoro-propene (HFO-1234yf) in of cls. 4 and
an amount of from 5% by weight to 6 of the ‘451
99% by weight of the heat-transfer Patent. The
fluid; and method of
(b) using said heat-transfer fluid cl. 36 of the
to absorb heat from the air in the Indian Patent
automobile by evaporating in said is not recited
evaporator said heat-transfer fluid in the claims
to produce a vapor comprising said of the ‘451
HFO-1234yf; Patent.

(c) compressing at least a portion of

said vapor from said step (b) in said
at least one compressor to produce
a relatively elevated pressure vapor
comprising HFO-1234yf; and

(d) removing heat from said relatively

elevated pressure vapor by condens-
ing said vapor.

Status of Legal Challenges: Patents Related to the Use of HFO-1234yf in Auto Air Conditioning
23
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INDIA 250569: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
37. The method as claimed in claim NA See cl. 5 Was the NA NA NA NA NA
5 wherein said lubricant is selected above. This same as
from the group consisting of polyol would not be original cl.
esters, polyalklene glycols, polyal- HFO-1234yf. 13, which
kylene silicon oils, mineral oils, alkyl However, the was can-
benzenes, poly(alpha-olefins) and list of lubri- celed during
combinations of these. cants is in cl. re-exam; and
9 of the ‘451 is the same
Patent. cls. 41 and

Center for Climate and Energy Solutions

51.
38. The method as claimed in claim Cl. 1 See cl. 5 Cls. 14, 34 Cls. 8, 10 Cl. 1 in part, Cl. 6 Cl. 1 in Cl. 4
5 wherein said at least one lubricant above. This and 12. and cls. 5 part, and
comprises at least one polyalkylene would not be and 18 cl. 5
glycol. HFO-1234yf.
However, the
lubricant is in
cl. 10 of the
‘451 Patent.
39. The method as claimed in claim NA See cl. 5 Cl. 15, 43 NA NA NA NA NA
5 wherein said at least one lubricant above. This
comprises polyalkylene glycol ester. would not be
HFO-1234yf.
However, the
lubricant is in
cl. 11 of the
‘451 Patent.
40. The method as claimed in claim Cl. 20; cl. NA Cl. 35, 44, Cl. 13, with- NA NA NA NA
5 wherein said heat-transfer fluid has 16 regard- 48 out GWP
a capacity relative to HFC-134a of ing (COP) limitation.
1 and a Coefficient of Performance relative to
(COP) relative to HFC-134a of 1. HFC-134a of
1 only.
 INDIA 250569: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
41. The method as claimed in Cl. 20 NA Cls. 35, Cls. 1 and NA NA NA NA
claim 39 wherein said heat-transfer regarding 44, and 48 14 regarding
composition has one liquid phase heat-transfer regarding temp. range
at at least one temperature between composi- heat-transfer and cl. 13
-50°C and +70°C and wherein said tion having composi- regarding
heat-transfer composition has a ca- a capacity tion having COP.
pacity relative to HFC-134a of 1 and relative to a capacity
a Coefficient of Performance (COP) HFC-134a relative to
relative to HFC-134a of 1. of 1 and a HFC-134a of
COP relative 1 and a COP
to HFC-134a relative to
of 1; cl. HFC-134a of
16 regard- 1 only.
ing (COP)
relative to
HFC-134a of
1 only.
42. The method as claimed in claim Cl. 12 See cl. 5 Cl. 45 Cl. 10 NA NA NA NA
41 wherein said fluoroalkene of For- above. This regarding
mula II comprises 1,1,1,2-tetrafluoro- HFO-1234yf HFO-1234yf,
propene (HFO-1234yf) present in the would be in without wt.
composition in an amount of at least a blend with % limitation.
70 % by weight. a different
fluoroalkene.
However,
the concept
of 70% of yf
is in cls. 4
and 23 of the
‘451 Patent.

Status of Legal Challenges: Patents Related to the Use of HFO-1234yf in Auto Air Conditioning
25
26
INDIA 250569: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
43. The method as claimed in NA Cl. 24 Cls. 24 and NA NA NA NA NA
claim 40 wherein said heat-transfer 46, but adds
composition comprises one or more that the
of the following: difluoromethane composi-
(HFC-32); tion “further
comprises”
pentafluoroethane (HFC-125); the listed
1,1,2,2-tetrafluoroethane (HFC-134); members.
1,1,1,2-

Center for Climate and Energy Solutions

tetrafluoroethane (HFC-134a); difluo-
roethane (HFC-152a); 1,1,1,2,3,3,3-

heptafluoropropane (HFC-227ea);
1,1,1,3,3,3-hexafluoropropane (HFC-
236fa); 1,1,1,3,3-pentafluoropropane
(HFC-245fa); 1,1,1,3,3-pentafluorobu-
tane (HFC-365mfc); water; and CO2.
44. The method as claimed in claim NA Cl. 7 Cl. 51 NA NA NA NA NA
36 wherein said heat-transfer fluid
comprises at least one lubricant
selected from the group consisting of
polyol esters, polyalkylene glycols,
polyalkylene silicon oils, mineral oils,
alkybenzenes, poly(alpha-olefins)
and combinations of these.
 INDIA 250569: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
45. The method as claimed in claim NA NA Cl. 47 recites Cls. 7 and 19 NA NA NA NA
44 wherein said system comprises a the condens-
condenser operated in a temperature er operating
range that includes 150°F. temperature
range in
connection
with a cool-
ing method
more general
than that in
cl. 36.
46. The method as claimed in claim Cl. 10 with Cl. 47 Cl. 52 Cl. 1 NA NA NA NA
45 wherein said heat-transfer fluid regard to the
has a Global Warming Potential lubricant-
(GWP) of not greater than 75. HFO-1234yf
composition.
47. The method as claimed in claim NA Cl. 47 de- Cl. 14, as it Cl. 12 Cl. 18 NA Cl. 7 when NA
14 wherein said at least one lu- pends from relates to cl. read with
bricant comprises a poly alkylene cl. 14 and 1 and cl. 8, cl. 5
glycol. cl. 14 recites HFO-1234ze.
a blend as
read with cl.
11, but the
lubricant is
recited in
cl. 10 of the
‘451 Patent.

Status of Legal Challenges: Patents Related to the Use of HFO-1234yf in Auto Air Conditioning
27
28
INDIA 250569: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
48. The method as claimed in NA NA Cl. 30, as Cls. 1, 13 NA NA NA NA
claim 47 wherein said heat-transfer it relates to
composition has one liquid phase cls. 1 and 8,
at at least one temperature between HFO-1234ze.
-50°C and +70°C and wherein said
heat-transfer composition has a
capacity relative to HFC-134a of 1,
a Coefficient of Performance (COP)
relative to HFC-134a of 1 and a

Center for Climate and Energy Solutions

Global Warming Potential (GWP) of
not greater than 75.
 ATTACHMENT 3: Chinese Patent 1732243

CHINA 1732243: COMPOSITION

CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
Status Rejected Rejected Rejected Rejected Rejected Rejected Rejected Rejected
claims from claims from claims from claims from claims from claims from claims from claims from
US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 469975819 JP 4571183

(PTAB (Request (Request (Request (on appeal) (final) (final) (on appeal)
decision for rehear- for rehear- for rehear-
appealed to ing of PTAB ing of PTAB ing of PTAB
Federal Cir- decision decision decision
cuit on May filed May 2, filed May 2, filed May 2,
3, 2016) 2016) 2016) 2016)
1. A heat-transfer composition, Cl. 1 is to Cl. 1 is to Although to Although Cl. 1 is to Cl. 1 is to The heat- Cl. 1 is to
including: the HFO- the HFO- a method, directed to a the HFO- the HFO- transfer the HFO-
1234yf 1234yf the fluoro- method, Cl. 1234 subset 1234 subset constituent 1234 subset
(A) at least one fluoro-olefin with subset of subset of alkene of 1 includes, of the flu- of the fluo- of Cl. 1 is to of a fluoro-
formula I: the fluoro- the fluoro- Cl. 1 is to in part, the oro-olefins ro-olefins of the Formula olefin of
XCFzR3-z (I) olefins of olefins of the Formula fluoro-olefin of Formula Formula (I). (II) subset of Formula (I).
Formula Formula (II), (II) subset of of cl. 1 of (I), with a Formula (I).
wherein X is unsaturated, which is (I), with a with a GWP Formula (I). the Chinese lubricant.
replaced or and replaces without C2 lubricant. limitation patent, but
or C3 –alkyl, The GWP not greater the GWP is
limitation is than 1000. not greater
R is independently Cl, F, Br, I or H,
in cl. 2. than 75.
and z is 1 to 3;

the heat-transfer compound having

less than about 150 global warming
potential (GWP).

Status of Legal Challenges: Patents Related to the Use of HFO-1234yf in Auto Air Conditioning
29
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CHINA 1732243: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
2. such as a heat-transfer composi- Cl. 1 is to Cl. 1, but Although NA Cl. 1 is Cl. 1 is Cl. 1, in part Cl. 1 is
tion described in claim 1, wherein at the HFO- GWP in directed to a to the to the except R is to the
least one fluorine compound of the 1234yf ‘451 Pat- method, cl. HFO-1234 HFO-1234 F or H and HFO-1234
olefin is a type II: subset of ent is “not 1 includes, subset of subset of at least one subset of
R R the fluoro- greater than in part, the the fluoro- the fluoro- R on end the fluoro-
C C R’ olefins of 1000” and compound olefins of olefins of unsaturated olefins of
Formula (II). there is of cl. 2 of Formula (II). Formula (II). C is H. Formula (II).
R
a 5–99% the Chinese
each one of those R is independently by weight patent.

Center for Climate and Energy Solutions

Cl, F, Br, I or H, range.
R’ is (CR 2)nY, and

N is 0 or 1.
3. such as heat-transfer composition The HFO- Cl. 1 Cl. 1 Cls. 4, 6 The HFO- The HFO- Cl. 1 The HFO-
described in claim 2, where Y is the 1234yf result in the 1234 subset 1234 subset 1234 subset
CF3. subset of cl. composition of cl. 1 of cl. 1 of cl. 1
1 meets this of cl. 3. meets this meets this meets this
limitation. limitation. limitation. limitation.
4. heat-transfer compositions de- The HFO- Cl. 1 Cls. 1, 36 Cl. 1 in part The HFO- The HFO- Cl. 1 The HFO-
scribed in claim 3, wherein [in] the 1234yf for subset of regarding 1234 subset 1234 subset 1234 subset
unsaturated carbon at least an R at subset of cl. Formula (II); Formula (I). of cls. 1, 12, of cls. 1 and of cls. 1 and
the end was not F. 1 meets this cl. 2 in part. 16, 17 (yf) 7 (yf) meet 5 (yf) meet
limitation. meet this this limita- this limita-
limitation. tion tion.
5. such as heat-transfer compositions The HFO- Cl. 1 Cl. 1 in part Cls. 1 and The HFO- The HFO- Cl. 1 The HFO-
described in claim 4, wherein [on] 1234yf sub- 14 in part 1234 subset 1234 subset 1234 subset
the carbon at the unsaturated end at set meets regarding of cls. 1, 12, of cls. 1 and of cls. 1 and
least one R is H. this limita- Formula (I). 16, 17 (yf) 7 (yf) meet 5(yf) meet
tion. meet this this limita- this limita-
limitation. tion. tion.
 CHINA 1732243: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
6. such as heat-transfer compositions The HFO- Cl. 2 Cl. 3 The Formula The HFO- The HFO- Cl. 1 The HFO-
described in claim 2, in which n is 0. 1234yf (II) subset of 1234 subset 1234 subset 1234 subset
subset of cl. cls. 4 and of cls. 1, 12, of cls. 1 and of cls. 1 and
1 meets this 14 achieve 16, 17 (yf) 7 (yf) meet 5(yf) meet
limitation. same result. meet this this limita- this limita-
limitation. tion. tion.
7. such as heat-transfer compositions The HFO- Cl. 2 Cls. 1, 3 The Formula The HFO- The HFO- Cl. 1 The HFO-
described in claim 2, where Y is the 1234yf (II) subset of 1234 subset 1234 subset 1234 subset
CF3, and n is 0. subset of cl. Cls. 1 and 4 of cls. 1, 12, of cls. 1 and of cls. 1 and
1 meets this achieve the 16, 17(yf) 7 (yf) meet 5 (yf) meet
limitation. same result. meet this this limita- this limita-
limitation. tion. tion.
8. such as heat-transfer compositions The HFO- The yf The yf The yf Cl. 1 Cl. 1 The yf Cl. 1
described in claim 1, wherein at least 1234yf subset of subset of subset of includes includes subset of includes
one fluorine alkene comprising at subset of cl. HFO-1234 HFO-1234 HFO-1234 HFO-1234, HFO-1234, HFO-1234 HFO-1234,
least one allyl PTFE (HFO-1234). 1 meets this is in cls. 4 is in cls. 7, is in cl. 10. but not the but not the is in cl. 8. but not the
limitation. and 6. 11, 32, 37, rest of the rest of the rest of the
39, 47, 50. claim in the claim in the claim in the
Chinese Pat- Chinese Pat- Chinese Pat-
ent. ent. ent.
9.–10. Directed to non HFO-1234yf. -- -- -- -- -- -- -- --
11. such as heat-transfer composi- NA NA NA NA Cl. 1 Cl. 1 NA Cl. 1
tions described in claim 8, wherein includes includes includes
at least one allyl PTFE (HFO-1234) HFO-1234, HFO-1234, HFO-1234,
including at least one where the but not the but not the but not the
unsaturated end have at most one rest of the rest of the rest of the
F substituent on the carbon com- claim in the claim in the claim in the
pounds. Chinese Pat- Chinese Pat- Chinese Pat-
ent. ent. ent.

Status of Legal Challenges: Patents Related to the Use of HFO-1234yf in Auto Air Conditioning
31
32
CHINA 1732243: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
12. such as heat-transfer composi- NA NA NA NA Cl. 1 Cl. 1 NA Cl. 1
tions described in claim 11, wherein includes includes includes
at least one allyl PTFE (HFO-1234) HFO-1234, HFO-1234, HFO-1234,
basically consists of unsaturated end but not the but not the but not the
referred to therein have at most one rest of the rest of the rest of the
F substituent on the carbon com- claim in the claim in the claim in the
pounds. Chinese Pat- Chinese Pat- Chinese Pat-
ent. ent. ent.

Center for Climate and Energy Solutions

13.–14. Directed to non HFO-1234yf. -- -- -- -- -- -- -- --
15. a thermal conduction to a fluid The HFO- Cl. 1 is the Cl. 1 recites Cl. 1 recites Cl. 1 is Cl. 1 is The heat- Cl. 1 is to
or fluid or subject or from a main 1234yf sub- Formula (II) a similar a similar to the to the transfer con- the HFO-
method of heat conduction, which set meets subset of method but formula for HFO-1234 HFO-1234 stituent of 1234 subset
include fluoro-olefin-I under a phase the Formula Formula(I), with the a method of subset of subset of Cls. 1 and 5 of a fluoro-
change occurs: XCFz R 3-z (I) where (I) descrip- but does not formula of cooling, but the fluoro- the fluoro- are subsets olefin that
X is an unsaturated, which replaced tion. recite the cl. 2 of the R is F or H. olefins that olefins that of a fluoro- meets this
or replaced without C2 or C3 – alkyl method. Chinese Pat- meet this meet this olefin that limitation.
group and independent for each R[is] ent. limitation. limitation. meets this
Cl, F, Br, I, or H and z=1-3. limitation.
16. such as the method of claim 15, NA NA NA NA NA NA NA NA
wherein the fluoro-olefin includes a
have at most one unsaturated carbon
at the end of the F substituent.
17. such as a method referred to in The HFO- Cl. 2 recites Cl. 3 recites Cl. 4, but for Cl. 1 is Cls. 1 and The heat- Cl. 1 is to
claim 16, z=3. 1234yf n=0, result- n=0, result- a method of to the 7 are to the transfer con- the HFO-
subset of cl. ing in a ing in a cooling. HFO-1234 HFO-1234 stituent of 1234 subset
1 meets this similar struc- similar struc- subset of subset of Cls. 1 and 8 of a fluoro-
limitation. ture. ture. the fluoro- the fluoro- are subsets olefin that
olefins that olefins that of a fluoro- meets this
meet this meet this olefin that limitation.
limitation. limitation. meet this
limitation.
 CHINA 1732243: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
18. such as the method of claim 17, The HFO- Cl. 1 meets Cls. 1, 36 Cl. 1 for Cl. 1 in part The HFO- The HFO- Cl. 1
wherein [on] the unsaturated end at 1234yf this limita- for subset of subset of regarding 1234 subset 1234 subset
least one substituent on the carbon subset of cl. tion for the Formula (II). Formula (II); Formula (I). of cls. 1, 12, of cls. 1 and
is not F. 1 meets this composition cl. 2 in part. 16, 17 (yf) 8 meet this
limitation. of Formula meet this limitation.
(II). limitation

19. such as a method referred to in The HFO- Cl. 1, in Cl. 1 meets Cls. 1, 14 Cls. 1 and Cl. 1 is Cls. 1 and 8 Cls. 1 and 5
claim 18, wherein [on] the unsatu- 1234yf part, meets this limita- 7 are to to the are sub- are sub-
rated end at least one substituent on subset of cl. this limita- tion for the HFO-1234 HFO-1234 sets of the sets of the
the carbon is H. 1 meets this tion for the composition subsets of subset of fluoro-olefin fluoro-olefin
limitation. composition of Formula the fluoro- the fluoro- that meet that meet
of Formula (II). olefins that olefins that this limita- this limita-
(II). meet this meet this tion. tion.
limitation. limitation.
20. such as a method referred to NA Cl. 1 em- Cls. 1, 8, 9, Cl. 6, but for Cl. 7, 12, 16 The HFO- Cl. 7 The HFO-
in claim 16, where X is a C2 alkyl bodies a 36 meet the a method of 1234 subset 1234 subset
group. subset that limitations cooling. of cl. 1 of cl. 1
could meet of this claim. meets this meets this
this limita- limitation. limitation.
tion.
21. such as a method referred to in The HFO- Cl. 1 em- Cl. 1+3, Cls. 4+6, Cl. 7, 12, 16 The HFO- Cl. 1, Y is The HFO-
claim 16, where Y is the CF 3 and X 1234yf bodies a 36 recites but for a recite com- 1234 subset CF3, but 1234 subset
[is] a C2 n. subset of cl. subset that subsets that method of positions of cl. 1 with the of cl. 1
1 meets this could meet meet this cooling. that meet meets this compound meets this
limitation. this limita- limitation, this limita- limitation. of Formula limitation.
tion. with the tion. (II) and there
formula of is no n
cl. 2 of the value, cl.7
Chinese Pat- may meet
ent. this limita-
tion.

Status of Legal Challenges: Patents Related to the Use of HFO-1234yf in Auto Air Conditioning
22–44. directed to non HFO-1234yf NA NA NA NA NA NA NA NA
and/or other applications.

33
34
CHINA 1732243: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
45. a compatibility composition, Cl. 1 is to Cl. 1 recites Cls. 1 and Cls. 1 and The HFO- The HFO- Cl. 1 recites Cl. 1
which is used for improved heat- the HFO- a subset of 36 recite a 14 recite 1234 subset 1234 subset a compound recites the
transfer fluids and lubricants for 1234yf the fluoro- composi- methods us- of cl. 1 of cl. 1 that is a HFO-1234
compatibility, the compatibility com- subset of olefin of tion that ing a similar meets the meets the subset of the subset of the
position including at least a fluoro- the fluoro- cl. 45. The meets the fluoro- fluoro-olefin fluoro-olefin fluoro-ole- fluoro-olefin
olefin with type I: olefins of GWP limita- fluoro-olefin alkene, in limitation limitation fin, but not of this claim,
Formula (I). tion is in limitation. part. with a lubri- but not the the rest of but not the
XCF zR 3-z (I) The GWP cl. 16; cl. cant, but not rest of the the claim. rest.
where X is an unsaturated, which limitation 13 adds a the rest of claim.

Center for Climate and Energy Solutions

replaced or replaced without C2 or is in cl. 2; compatibi- the claim.
C3 –alkyl, R [is] independent[ly] Cl, cl. 3 recites lizer.
F, Br, I, or H and z [is] 1 to 3, the a compat-
compatibility composition having ibilizer.
a less than about 150 of the global
warming potentials (GWP).
46. claim 45 the compatibility com- Cl. 9 Cls. 16 and Cl. 16 re- Cl. 14 re-
position, wherein the GWP is not 45 recites cites a GWP cites a GWP
greater than 100 percent. GWP not not greater not greater NA NA NA NA
greater than than 150. than 150.
150.
47. such as increasing capacity Cl. 11 has Concept Concept NA NA NA NA NA
referred to in claim 45 compositions, ODP not appears in was in Cl.
having not more than 0.05 percent of greater than Cls. 18 and 18, but with
ozone-depletion potential (ODP). 0.02. 45, but for a the formula
composition of cl. 2 of
similar to an the Chinese
embodiment Patent, but
of cl. 2 of canceled
the Chinese during re-
patent. exam.
 CHINA 1732243: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
48. as described in the claim 45 the NA NA NA NA NA NA NA NA
capacity increase of composition
wherein fluorine alkene includes a
have at most one unsaturated carbon
at the end of the F substituent.
49. as described in the claim 45 the The HFO- Cl. 1, in Cl. 1 meets Cls. 1, 14 Cls. 1 and Cl. 1 is Cls. 1 and 8 Cls. 1 and 5
capacity increase of composition 1234yf part, meets this limita- 7 are to to the are sub- are sub-
wherein fluorine alkene, including subset of cl. this limita- tion for the HFO-1234 HFO-1234 sets of the sets of the
end of an unsaturated carbon and 1 meets this tion for the composition subsets of subset of fluoro-olefin fluoro-olefin
unsaturated end mentioned at least limitation. composition of Formula the fluoro- the fluoro- that meet that meet
one substituent on the carbon is H. of Formula (II). olefins that olefins that this limita- this limita-
(II). meet this meet this tion. tion.
limitation. limitation.
50–53 directed to a disinfectant NA NA NA NA NA NA NA NA

Status of Legal Challenges: Patents Related to the Use of HFO-1234yf in Auto Air Conditioning
35
36
CHINA 1732243: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
54. a composition which includes: Cl. 1 is to Cl. 1 recites Cl. 1 recites Cls. 1 and Cls. 1 and Cl. 1 recites Cl. 1 recites Cl. 1
the HFO- a subset of a subset of 14 recite 12 recites a a subset of a subset of recites the
(A) at least a fluoro-olefin with type 1234yf the fluoro- the fluoro- methods subset of the the fluoro- the fluoro- HFO-1234
I: subset of olefin of olefin of cl. that include fluoro-olefin olefin of olefin of cl. subset of the
XCF zR 3-z (I) the fluoro- cl. 54. Cl. 54 with a a composi- and lubri- cl. 54; cl. 54 with a fluoro-olefin
olefins of 7 adds a lubricant. tion of cant. 4 adds a lubricant. of cl. 54;
where X is an unsaturated, which Formula lubricant. Formula (I), lubricant. cl. 2 adds a
replaced or replaced without C2 or (I), with a in part, with lubricant.
C3- alkyl group and independent for lubricant. a lubricant.

Center for Climate and Energy Solutions

each R [is] Cl, F, Br, I, or H and z for
1 to 3; Cl. 18
recites sur-
(B) at least a junior agent, by said factant.
junior agent is selected free follow-
ing material composition of group:
lubricant, and increased capacity
agent, and surfactant, and increased
solvent, and dispersed agent, and
bubble hole stable agent, and ap-
pearance modified agent (cosmetics),
and polishing agent, and pharmacy,
and clean agent, and flame retar-
dant agent, and coloring agent, and
chemical disinfectant, and stable
agent, and multiple alcohol, and
multiple alcohol pre mixed compo-
nent and the these material in the of
two species or two species above
material of combination.
 CHINA 1732243: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
55. as described in the claim 54 Cl. 2 if the Cl. 16 in Cl. 16 but Cl. 14 NA NA NA NA
composition not more than about structure part, if the with the
150 of their global warming poten- of cl. 54 is structure composition
tials (GWP). limited to of cl. 54 is of cl. 2 of
constituents limited to the Chinese
of HFO- the structure Patent.
1234yf. of cl. 2 of
the Chinese
Patent.
56. as described in claim 55 compo- Cl. 1 is to Cl. 1 in part, Formula (II) Cls. 8, 10, Cl. 1 recites Cl. 1 recites Cl. 1 in part, Cls. 1 and
sitions, wherein at least one fluorine the HFO- except Y is recited in 20 recites the HFO- the HFO- but Y is CF3 5 recite the
compound of the type II: 1234yf CF3. methods of HFO-1234 1234 subset 1234 subset with no HFO-1234
R R subset of cls. 1 and subsets of of cl. 56. of cl. 56. reference to subsets of
C C R’ the fluoro- 36. Formula (II) GWP. cl. 56, but
olefins of of cl. 56. with no
R
Formula (II). reference to
each one of those R is independently GWP.
Cl, F, Br, I or H,

R’ is (CR 2)nY

Y is CRF2,

and n is 0 or 1.
57. the compositions described in The HFO- Cl. 1, in Formula (II) Cls. 1 and Cl. 1 recites Cl. 1 recites Cl. 1, but Cl. 1 recites
claim 56, where Y is the CF3. 1234yf part. recited in 14 recite the HFO- the HFO- with no the HFO-
subset of cl. methods of comparable 1234 subset 1234 subset reference to 1234 subset
1 meets this cls. 1 and composi- of cl. 56. of cl. 56. GWP. of cl. 56.
limitation. 36. tions; cl. 14
recites the
same. GWP
(see cl. 55).

Status of Legal Challenges: Patents Related to the Use of HFO-1234yf in Auto Air Conditioning
37
38
CHINA 1732243: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
58. if the compositions described in The HFO- Cl. 1 meets Cls. 1, 36 Cl. 1 for Cl. 1 in part The HFO- The HFO- Cl. 1 recites
claim 56, wherein [on] the unsatu- 1234yf this limita- for subset of subset of regarding 1234 subset 1234 subset HFO-1234
rated carbon at least an R at the end subset of cl. tion. Formula (II). Formula (II); Formula (I). of cls. 1, 12, of cls. 1 and subset of cl.
was not F. 1 meets this cl. 2 in part. 16, 17 (yf) 8 meet this 58.
limitation. meet this limitation.
limitation.

59. the compositions described in The HFO- Cl 1 Formula (II) Cl. 1 for Cl. 1 in part The HFO- Cl. 1 Cl. 1 recites

Center for Climate and Energy Solutions

claim 56, wherein [on the] carbon 1234yf recited in subset of regarding 1234 subset HFO-1234
unsaturated end at least one R is H. subset of cl. methods of Formula (II); Formula (I). of cls. 1, 12, subset of cl.
1 meets this cls. 1 and cl. 2 in part. 16, 17 (yf) 59.
limitation 36. meet this
limitation.

60. including such as heat-transfer Cl. 1 Cl. 7 in part Cl. 1 The heat- Cl. 1 Cl. 4 Cl. 1 Cl. 2 with
compositions described in claim 54 transfer includes a includes a HFO-1234.
compositions wherein the adjuvant fluids used lubricant lubricant
includes at least one lubricant. in the meth- with HFO- with HFO-
ods include 1234. 1234.
a lubricant
and the
composition
of Formula
(I).
61. includes such as heat-transfer NA NA NA NA NA NA NA NA
compositions described in claim 54
composition, increasing capacity of
the adjuvant includes at least one
agent.
 CHINA 1732243: COMPOSITION
CONTAINING FLUORINE
SUBSTITUTED OLEFINS US ‘366 US ‘451 US ‘882 US ‘120 EP 1563032 EP 1716216 JP 4699758 JP 4571183
62. such as heat-transfer composi- Cls. 1 + NA NA NA NA NA NA NA
tions described in claim 61, wherein 4 for the
the compounds of formula I is at HFO-1234yf
least about 50% the weight, and the subset of
weight of the lubricant quantity is at cl. 1.
least about 30%.
63.-65. Directed to foaming agent NA NA NA NA NA NA NA NA
applications.
66. as described in the claim 54 Cl. 1 in part NA Cl. 1 in part, Cl. 3 NA NA NA NA
compositions, which generally do if cl. 1 of with the
not have acute toxicity. Chinese pat- Formula (ii)
ent is lim- compound.
ited to HFO-
1234yf.
67. the compositions described NA NA NA Cl. 2 NA NA NA NA
in claim 54, which has low acute
toxicity, wherein the compounds of
formula I composed essentially of
one or more compounds, wherein
the fluoro-olefin includes a have at
most one unsaturated carbon at the
end of the F substituent.
68. as described in the claim 54 The HFO- Cl. 1, in Cl. 1 meets Cl. 1, in Cl. 1 meets Cl. 1 is Cls. 1 and 8 Cls. 1 and 5
compositions, it has low acute 1234yf part, meets this limita- part, meets this limita- to the are sub- are sub-
toxicity, wherein the compounds of subset of cl. this limita- tion for the this limita- tion for the HFO-1234 sets of the sets of the
formula I composed essentially of 1 meets this tion for the composition tion for the composi- subset of fluoro-olefin fluoro-olefin
one or more compounds, wherein limitation, composition of Formula composi- tion of For- the fluoro- that meet that meet
the fluoro-olefin including end of an but states of Formula (II), exclud- tion of For- mula (II). olefins that this limita- this limita-
unsaturated carbon and unsaturated “no substan- (II), exclud- ing the low mula (II). meet this tion, exclud- tion, exclud-
end mentioned at least one substitu- tial acute ing the low toxicity re- limitation, ing the low ing the low
ent on the carbon is H. toxicity.” toxicity re- quirement. excluding toxicity toxicity
quirement. the low tox- requirement. requirement.

Status of Legal Challenges: Patents Related to the Use of HFO-1234yf in Auto Air Conditioning
icity require-
ment.

39
 ENDNOTES
1 Divisional, continuation, and continuation-in-part (CIP) applications (collectively, continuing applications),
may be filed during the pendency of a prior filed application based on the same text as the prior filed application, or in
the case of CIPs, based on a modified text, but have claims that differ from the claims of any patent granted on the prior
filed application. Continuing applications claim priority to at least the immediately prior filed application and are treated
for purposes of determining dates of expiration and what constitutes prior art, as having been filed on the same day as the
earliest claimed priority application. CIPs are not authorized in most countries, but are in the United States.

2 A large number of production process patents have been filed by transnational chemical companies (e.g.,
Arkema, Mexichem, Chemours, and Honeywell) in many of the larger developed and developing countries. In addition, a
number of Chinese entities have also filed production process patents and SRF (India) has also recently announced plans
to begin a pilot plant to produce HFO-1234yf using its own unique process. Issues concerning production process patents
are not addressed in this paper.

3 A demonstration project on this technology is being conducted by TATA Motors Limited, MAHLE, and the
Institute for Governance and Sustainable Development under a grant from the Climate and Clean Air Coalition.

4 The European Commission has issued a Statement of Objections (Oct. 21, 2014) to Honeywell and DuPont (now
Chemours) raising antitrust issues concerning their 2010 cooperation agreement on the development of HFO-1234yf for
use in auto air conditioning. While potentially significant, this paper focuses solely on legal challenges to patents and does
not address this antitrust action.

5 Honeywell has signed purchase agreements with a number of other chemical producers for supplying HFO-
1234yf. It has an agreement with Chemours and has recently announced agreements with Navin (India) and Juhua (China)
to supply HFO-1234yf to Honeywell.

6 Patents contain lists of the specific “claims” made by the patent holder that define the extent or scope of the
protection conferred by a patent and what it is that the patent holder can prohibit others, without a license, from making,
using, selling or importing into the country that granted the patent.

7 We report on the status of the challenges only and offer no opinion as to the correctness of the outcomes of the
challenges to any of the patents discussed herein.

8 In addition to direct challenges to a number of patents, Arkema is pursuing a case in the U.S. District Court for
the Eastern District of Pennsylvania seeking a declaratory judgment of invalidity of four Honeywell patents in the United
States on the use of HFO-12234yf in auto air conditioning that are discussed in this section. The case was stayed pending
the final outcome of the inter partes reexamination proceedings on these patents. See Arkema Inc. et al. v. Honeywell Inter-
national Inc., No. 10-CV-02886.

9 While US ‘017 was filed in October 2014, it claims priority based on previously filed patents that date back to
2003. As a result, despite being filed in 2014, this patent would expire in October 2023. See section V below.

10 In addition, US 9,005,467 was recently issued, but appears to be specific to the use of HFO-1234yf as a drop-in
substitute in existing HFC-134a systems.

11 In addition to EP ’654 and EP ’970, there are other European applications pending that are relevant to the use
of HFO-1234yf in automobile air conditioning. By way of example: EP 2277971 and EP 2277972 (both are divisionals of EP
’032); EP 2258802 and EP 2277977 (both divisionals of EP 1716216).

12 Within limits provided the claims are based on subject matter disclosed in the application as filed.

13 In documents submitted to the PTAB in connection with a challenge to US Patent No. 9,157,017, Honeywell
listed, as required, related proceedings including an opposition against Indian Patents 239049 and 250569, which are iden-
tified as foreign counterparts, respectively, to the US ’366 and US ‘451 and ‘017 patents.

40 Center for Climate and Energy Solutions

 14 Moreover, two other pending patent applications are at an advanced stage in the examination proceedings.
CN 103642461 (divisional of the Chinese counterpart of WO 2005/042663) and CN 103215013, a divisional of the Chinese
counterpart of WO 2005/042663.

15 In addition to claims related to auto air conditioning, CN 1732243 contains claims that are specific to the use of
HFOs in foam, as a solvent, and fire suppressant agent. This analysis focuses only on those claims related to auto air condi-
tioning.

16 Subject to the outcome of pending appeals, re-opened prosecution, and rehearing requests.

17 The comparison for both Japanese patents is based on machine translations of the Japanese claims.

18 Ibid.

19 Ibid.

Status of Legal Challenges: Patents Related to the Use of HFO-1234yf in Auto Air Conditioning 41
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