Application No. 10/694,273
`
`Docket No. H0003965US
`
`IN THE UNITED STATES PATENT AND TRADEMARK OFFICE
`
`In re application of: R. Singh, et al.
`
`Examiner: A. Khan
`
`Application No.:
`
`10/694,273 (Conf. 2796)
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`Group Art Unit: 1751
`
`Filed:
`
`October 27, 2003
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`Docket No.: H0003965-4510
`
`Title: COMPOSITIONS CONTAINING FLUORINE SUBSTITUTED OLEFINS
`
`To:
`
`Commissioner for Patents
`
`P. O. Box 1450
`
`Alexandria, VA 22313-1450
`
`RESPONSE TO THE OFFICE ACTION DATED AUGUST 29 2007
`
`Sir:
`
`This is in response to the non—final Office Action mailed August 29, 2007,
`
`having a period for reply set to expire November 29, 2007.
`
`Amendments to the claims appear on page 2.
`
`Remarks begin on page 8.
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`1 of 13
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`Arkema Exhibit 1039
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`Arkema Exhibit 1039
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`Application No. 10/694,273
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`Docket No. H0003965US
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`LISTING OF CLAIMS
`
`The following listing of claims replaces all prior versions:
`
`LISTING OF CLAIMS
`
`1. — 53. (Canceled)
`
`54. (Currently Amended)
`
`m0CA
`
`n.m...H.SOD.
`
`comprising:
`
`(b) at least one adjuvant selected from the group consisting of lubricants,
`
`compatibilizers, surfactants, solubilizing agents, dispersing agents, cell
`
`stabilizers, cosmetics, polishing agents, medicaments, cleaners, fire
`
`retarding agents, colorants, chemical sterilants, stabilizers, polyols, polyol
`
`premix components and combinations of two or more of these.
`
`55.
`
`(Original) The composition of claim 54 having a Global Warming Potential
`
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`(GWP) of not greater than about 150.
`
`
`
`Cancelled
`
`60.
`
`61.
`
`62.
`
`63.
`
`64.
`
`65.
`
`(Original) A heat transfer composition comprising the composition of claim
`
`54 wherein said adjuvant includes at least one lubricant.
`
`(Original) A heat transfer composition comprising the composition of claim
`
`54 wherein said adjuvant includes at least one compatibilizer.
`
`(Currently Amended) The heat transfer composition of claim
`
`4
`,2,
`.— wherein
`
` said
`
`is present in an amount of at
`
`least about 50% by weight and said lubricant is present in an amount of at
`
`least about 30% by weight.
`
`(Currently Amended) A blowing agent comprising the composition of claim
`
`54 wherein said adjuvant includes 5
`
` 54 wherein said .,,,,
`
` amount of
`
`(Original) A sterilant composition comprising the composition of claim 54
`
`wherein said adjuvant includes at least one chemical sterilant.
`
`66.
`
`— 68.
`
`Cancelled.
`
`69.
`
`(Previously Presented) The composition of claim 54 wherein said
`
`composition is non-flammable.
`
`70. — 75. (Cancelled)
`
`76.
`
`77.
`
`78.
`
`79.
`
`(Previously Presented)
`
`The composition of claim 54 having a Global
`
`Warming Potential (GWP) of not greater than about 100.
`
`(Previously Presented)
`
`The composition of claim 54 having a Global
`
`Warming Potential (GWP) of not greater than about 75.
`
`(Cancelled)
`
`(Previously Presented)
`
`The composition of claim 54 having an ODP of
`
`not greater than about 0.02.
`
`80.
`
`(Cancelled)
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`81.
`
`(Currently Amended) The composition of claim 54 wherein said
`
`composition is a refrigerant compositions and said
`.-\-..-« .«\-x » -.—x-
`-
`,.\ .('
`..
`..
`"§Z~‘§‘
`»...,-,,,.
`
`
`\‘.:-\‘.:»‘t‘:‘t;t:- “:-‘oi
`
`composition.
`
`82.
`
`83- i:::.
`
`(Currently Amended) The composition of claim ‘
`wherein said compatibilzer
`
`
`
`
`pro pan e_.___‘
`
`5
`.wm.-;.\..—... M.
`..
`.
`
`-~:2S:t:>r~r:>+.:rtr<::w:*~:
`
`85.
`
`(Currently Amended) The composition of claim
`
`comprising
`
`compatibilzer in amounts of from about 0.5 to about 5 percent by weight of
`
`Vi“
`
`
`
`the composition.
`
`86.
`
`(Currently Amended) The composition of claim
`
`wherein said sterilant is selected from the group consisting of
`
`ethylene oxide (EO), formaldehyde, hydrogen peroxide, chlorine dioxide,
`
`ozone, and combinations of these.
`
`87. — 90. Canceled
`
`91.
`
`(Currently Amended) The composition of claim 54 wherein said _§;;_
`.
`.
`....
`.
`-5;-x .~\-\ ;~ - M .-
`; »-x .-\-
`- -4- \. .-\ -.- mu .
`.~ - .-
`I
`
`
`2-\:m‘t-:-tp ‘:»‘z:a-Hi:
`':.\:--~.‘“:::~.“h‘~.‘:::~I
`v;
`
`is present in the composition in an amount
`
`of at least about 50% by weight.
`
`92.
`
`(Currently Amended) The composition of claim 54 wherein said
`x
`a
`
`
`
`iiwis present in the composition in an
`
`amount of at least about 70% by weight.
`
`93.
`
`(Previously Presented) A refrigerant comprising the composition of claim
`
`54, said refrigerant comprising lubricant in an amount of from about 30 to
`
`about 50% by weight.
`
`94.
`
`(Previously Presented) The composition of claim 54 comprising a
`
`surfactant and a solubilizing agent.
`
`95.
`
`(Previously Presented) The composition of claim 54 comprising lubricant
`
`wherein said lubricant is selected from the group consisting of polyol
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`esters, poly alkylene glycols and combinations of these.
`
`96
`
`(Previously Presented) The composition of claim 95 wherein said lubricant
`
`comprises at least one polyalkylene glycol.
`
`97.
`
`(Previously Presented) The composition of claim 95 wherein said lubricant
`
`comprises at least one polyol ester.
`
`98.
`
`(Previously Presented) The composition of claim 95 wherein said
`
`composition has one liquid phase at at least one temperature between
`
`about -50 °C and +70 °C.
`
`99.
`
`(Previously Presented) The composition of claim 54 comprising lubricant
`
`and being stable when in contact with aluminum, steel and copper under
`
`the conditions of use in refrigeration and air conditioning systems.
`
`100. (New) A composition having no substantial acute toxicity comprising:
`
`(a) 1,1,1,2,3 pentafluoropropene (HFO-1225ye); and
`
`(b) at least one adjuvant selected from the group consisting of lubricants,
`
`compatibilizers, surfactants, solubilizing agents, dispersing agents, cell
`
`stabilizers, cosmetics, polishing agents, medicaments, cleaners, fire
`
`retarding agents, colorants, chemical sterilants, stabilizers, polyols, polyol
`
`premix components and combinations of two or more of these.
`
`101.
`
`(New) The composition of claim 100 having a Global Warming Potential
`
`(GWP) of not greater than about 150.
`
`102.
`
`(New) A heat transfer composition comprising the composition of claim
`
`100 wherein said adjuvant includes at least one lubricant.
`
`103.
`
`(New) A heat transfer composition comprising the composition of claim
`
`100 wherein said adjuvant includes at least one compatibilizer.
`
`104.
`
`(New) The heat transfer composition of claim 102 wherein said HFO-
`
`1225ye is present in an amount of at least about 50% by weight and said
`
`lubricant is present in an amount of at least about 30% by weight.
`
`105.
`
`(New) A blowing agent comprising the composition of claim 100 wherein
`
`said adjuvant includes polyol, plyol premix components and combinations
`
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`of these.
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`106.
`
`(New) A blowing agent comprising the composition of claim 100 wherein
`
`said HFO-1225ye is present in an amount of at least about 5% by weight.
`
`107.
`
`(New) A blowing agent comprising the composition of claim 100 wherein
`
`said HFO-1225ye is present in an amount of at least about 15% by weight.
`
`108.
`
`(New) A sterilant composition comprising the composition of claim 100
`
`wherein said adjuvant includes at least one chemical sterilant.
`
`109. (New) The composition of claim 100 wherein said composition is non-
`
`flammable.
`
`110. (New) The composition of claim 100 having a Global Warming Potential
`
`(GWP) of not greater than about 100.
`
`111. (New) The composition of claim 100 having a Global Warming Potential
`
`(GWP) of not greater than about 75.
`
`112. (New) The composition of claim 100 having an ODP of not greater than
`
`about 0.02.
`
`113. (New) The composition of claim 100 wherein said composition is a
`
`refrigerant compositions and said HFO-1225ye comprises at least about
`
`70 % by weight of the composition.
`
`114. (New) The composition of claim 100 comprising compatibilzer and
`
`wherein said compatibilzer is selected from the group consisting of
`
`propane, butane, pentane and combinations of these.
`
`115. (New) The composition of claim 100 comprising compatibilzer in amounts
`
`of from about 0.5 to about 5 percent by weight of the composition.
`
`116. (New) The composition of claim 100 comprising sterilant and wherein said
`
`sterilant is selected from the group consisting of ethylene oxide (EO),
`
`formaldehyde, hydrogen peroxide, chlorine dioxide, ozone, and
`
`combinations of these.
`
`117.
`
`(New) The composition of claim 100 wherein said HFO-1225ye is present
`
`in the composition in an amount of at least about 50% by weight.
`
`118.
`
`(New) The composition of claim 100 wherein said HFO-1225ye is present
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`in the composition in an amount of at least about 70% by weight.
`
`119.
`
`(New) A refrigerant comprising the composition of claim 100, said
`
`refrigerant comprising lubricant in an amount of from about 30% to about
`
`50% by weight.
`
`120.
`
`(New) The composition of claim 100 comprising a surfactant and a
`
`solubilizing agent.
`
`121.
`
`(New) The composition of claim 100 comprising lubricant wherein said
`
`lubricant is selected from the group consisting of polyol esters, poly
`
`alkylene glycols and combinations of these.
`
`122.
`
`(New) The composition of claim 124 wherein said lubricant comprises at
`
`least one polyalkylene glycol.
`
`123.
`
`(New) The composition of claim 124 wherein said lubricant comprises at
`
`least one polyol ester.
`
`124.
`
`(New) The composition of claim 124 wherein said composition has one
`
`liquid phase at at least one temperature between about -50 °C and +70 °C.
`
`125.
`
`(New) The composition of claim 100 comprising lubricant and being stable
`
`when in contact with aluminum, steel and copper under the conditions of
`
`use in refrigeration and air conditioning systems.
`
`126.
`
`(New) The composition of claim 100 wherein said HFO-1225ye comprises
`
`cis-HFO-1225ye.
`
`127.
`
`(New) The composition of claim 100 wherein said HFO-1225ye comprises
`
`trans-HFO-1225ye.
`
`128.
`
`(New) The composition of claim 100 wherein said HFO-1225ye comprises
`
`a combination of cis-HFO-1225ye and trans-HFO-1225ye.
`
`129.
`
`(New) A blowing agent comprising the composition of claim 54 wherein
`
`said HFO—1234yf is present in an amount of at least about 15°/oby weight.
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`Application No. 10/694,273
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`Docket No. H0003965US
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`REMARKS
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`Reconsideration of the present application in view of the above
`
`amendments and the presently filed declaration is respectively requested.
`
`1.
`
`STATUS OF THE CLAIMS
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`Claims 54, 55, 60 — 65, 69, 76 — 79, 81, 82, 85, 86, 91 -129 are now
`
`pending in the present application. Claims 1 — 53, 56 — 59, 66 — 68, 70 -75, 78,
`
`80, 83 — 84, and 87 — 90 have been canceled. Claims 54, 62 — 64, 81, 82, 85, 86,
`
`91, and 92 have been amended. New claims 100 — 129 have been added.
`
`Support for the amendments and for the new claims can be found
`
`throughout the present specification and more specifically as follows.
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`Support for the amendment to claim 54 relating to the absence of
`
`substantial acute toxicity in compounds such as HFO-1234yf is found on page 6,
`
`lines 25 — 31.
`
`Support for the amendment to claim 64 relating to the preferred
`
`compound(s) being present in amounts of at least about 5% by weight is found
`
`on page 9, lines 13 -18.
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`Support for the amendment to claim 81 relating to the preferred
`
`compound(s) being present in amounts of at least about 70% by weight is found
`
`on page 8, lines 19 — 24.
`
`Support for the amendment to claim 82 relating to compatibilizers being
`
`propane, butanes and pentanes is found on page 9, lines 1 — 3.
`
`Support for new claim 129, which depends from claim 54, is found on
`
`page 9, lines 13 -18.
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`Support for the new independent claim 100, which is directed to HFO-
`
`1225ye, is found throughout the application as originally filed and in particular on
`
`page 6, lines 25 — 31.
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`Support for the new dependent claim 101 directed to GWP is found on
`
`page 8, line 8 and elsewhere throughout the application as originally filed.
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`Support for the new dependent claims 102 -104 directed to lubricants and
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`compatibilizers is found on pages 8 and 9, and elsewhere throughout the
`
`application as originally filed.
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`Support for the new dependent claim 105 directed to polyols and polyol
`
`premixes is found on page 12 and in the original claims, including original claim
`
`28, and elsewhere throughout the application as originally filed.
`
`Support for the new dependent claims 106 and 107 relating to the
`
`preferred compound(s) being present in amounts of at least about 5% by weight
`
`and 10% by weight is found on page 9, lines 13 -18.
`
`Support for the new dependent claim 108 relating to sterilant is found on
`
`pages 15 and 16, and elsewhere throughout the application as originally filed.
`
`Support for the new dependent claim 109 relating to the composition being
`
`non-flammable is found throughout the application as originally filed.
`
`Support for the new dependent claims 110 — 112 directed to GWPs and
`
`ODPs is found on page 8, line 4 -16 and elsewhere throughout the application
`
`as originally filed.
`
`Support for the new dependent claim 113 relating to the preferred
`
`compound(s) being present in amounts of at least about 70% by weight is found
`
`on page 8, lines 19 — 24.
`
`Support for the new dependent claim 114 and 115 relating to
`
`compatibilizers and percentages is found on page 9, lines 1 — 3.
`
`Support for the new dependent claim 116 relating to sterilants is found on
`
`pages 15 and 16, and elsewhere throughout the application as originally filed.
`
`Support for the new dependent claims 117 and 118 relating to
`
`percentages is found on page 8, lines 19 — 24, and elsewhere throughout the
`
`application as originally filed.
`
`Support for the new dependent claims 117 -125 relating to various
`
`aspects of compositions including lubricants and solubilizers and related
`
`properties is found at page 8, line 25 — page 9, line 9 and in Examples 2 and 3 on
`
`pages 18 and 19.
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`Support for the new dependent claims 126 — 128 relating to isomeric forms
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`of HFO-1225ye is found at page 6, lines 25 — 30.
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`II. RESPONSE TO THE OUTSTANDING OFFICE ACTION
`
`In the outstanding office action, the Examiner rejected the pending claims
`
`under 35 U.S.C. 103(a) as being unpatentable over Smits et al. (US 4,945,119)
`
`or over Smits in view of Nimitz et al. (US 5,674,451).
`
`In making this rejection,
`
`the Examiner took the position that the previously submitted Declaration under
`
`37 CFR 1.132 filed on June 25, 2007 was insufficient to overcome the rejection
`
`based on Smits et al. alone or in view of Nimitz et al.
`
`It was the Examiner’s
`
`positions that the declaration was not commensurate in scope with the claims
`
`pending in the application at that time.
`
`Applicants do not necessarily agree with the Examiner’s position that the
`
`declaration filed on June 25, 2007 is not sufficient to support patentability of the
`
`claims of the previously pending scope, and applicants expressly reserve the
`
`right to prosecute claims of a similar scope to those previously presented in an
`
`continuation or divisional application. Nevertheless, in order to facilitate
`
`prosecution of the present application, applicants have narrowed the scope of the
`
`pending claims and have submitted a further declaration in support of
`
`patentability.
`
`The pending claims comprise two sets of claims. The first set is based on
`
`independent claim 1, which is directed to compositions having no substantial
`
`acute toxicity and which include as an essential component 1,1,1,2-
`
`tetrafluoropropene (HFO-1234yf). The second set of claims is based on
`
`independent claim 100, which is directed to compositions having no substantial
`
`acute toxicity and which include as an essential component 1,1,1,2,3
`
`pentafluoropropene (HFO-1225ye). Each of these compounds share the
`
`characteristic of having a relatively low toxicity and each also shares the
`
`structural feature of have having at least one H on the unsaturated terminal
`
`carbon. As described in the present specification ( see page 5, lines 15 -19), this
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`structural feature has been discovered by applicants to contribute to the low
`
`toxicity characteristics of the compounds which are essential components of the
`
`present claims and which therefore contribute to the low acute toxicity of the
`
`composition. There is no suggestion in the prior art of this feature or its
`
`advantages.
`
`With respect to the first set of claims, applicants have found surprisingly
`
`that HFO-1234yf possesses a desirably low level of acute toxicity relative to
`
`structurally similar compounds. As described in the present application and as
`
`supplemented by the Rule 132 Declaration of George Rusch dated October 15,
`
`2007 ("the Second Rusch Declaration"), toxicological testing of a compound
`
`known as HFO-1225zc (1,1,3,3,3— pentafluoropropene):
`
`F3C
`
`H
`
`F
`
`F
`
`HFO-1225zc
`
`had been conducted by a third party prior to the filing of the present application.
`
`This testing revealed that this compound exhibited a relatively high level of
`
`toxicity. More specifically, the attached Second Rusch Declaration (see
`
`paragraph 2), revealed that HFO-1225zc had an LC50 or median lethal
`
`concentration required to kill half the members of a tested population, as low as
`
`2,000 ppm. Since LC50 represents the concentration at which a measure of
`
`lethality occurs, the lower the value of LC50, the more toxic the material is
`
`considered to be, and the higher the value, the less toxic the material is
`
`considered to be. This toxic compound, which is otherwise structurally similar
`
`HFO—1234yf and HFO-1225ye, does not have at least one H on the unsaturated
`
`terminal carbon.
`
`In contrast, HFO-1234yf, a structurally similar compound which is within
`
`the scope of claim 1 (2,3,3,3-tetrafluoropropene):
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`F31:
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`F
`
`H
`
`x.-.
`
`.__\ H
`
`HFO-1234yf
`
`was found by applicants to be much less toxic than HFO-1225zc (see, for
`
`example, paragraphs 3 and 4 of the Second Rusch Declaration). More
`
`specifically, the LC5O of HFO-1234yf, which has two hydrogen atoms on the
`
`unsaturated terminal carbon, has a toxicity concentration that is at least two
`
`hundred times greater than that of HFO-1225zc. This difference is dramatic
`
`and is in no way suggested or expected in view of any of the prior art cited by the
`
`Examiner or any other art known to applicants. Furthermore, HFO—1234yf has
`
`the additional advantage of having a relative capacity of greater than 1, which is
`
`substantially greater than even the tetrafluoropropene isomer 1,3,3,3-
`
`tetrafluoropropene (HFO-1234ze). As seen from Table l on page 18 of the
`
`present specification, HFO-1234ze has a relative capacity (based on HFC—134a)
`
`of either 0.36 or 0.7, depending on the stereoisomeric form thereof, whereas
`
`HFO—1234yf has a relative capacity of 1.1, which is much superior in terms of
`
`performance as a drop-in replacement for the heretofore commonly used HFC-
`
`134a.
`
`With respect to the second set of claims, applicants have also found
`
`surprisingly that HFO-1225ye (1 ,2,3,3,3-pentafluoropropene):
`
`F30
`
`F;
`
`H
`
`“F
`
`HFO—1225ye
`
`which is within the scope of claim 100, is much less toxic than HFO-1225zc
`
`(see, for example, paragraphs 3 and 4 of the Rusch Declaration filed on April 25,
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`2007). More specifically, the LC50 of HFO-1225ye, which is within the scope of
`
`claim 100 and which has one hydrogen on the unsaturated terminal carbon, has
`
`a toxicity concentration that is at least one hundred and twenty five times
`
`greater than that of HFO—1225zc, which is not within the scope of the claim 100.
`
`This difference is dramatic and is in no way suggested or expected in view of any
`
`of the prior art cited by the Examiner or any other art known to applicants.
`
`11.
`
`CONCLUSION
`
`Applicants believe that the claims as now pending patentably distinguish
`
`over the prior art of record, and an early notice thereof is hereby earnestly
`
`solicited. Should the Examiner have any questions regarding this further
`
`response, she is invited to contact the undersigned at the telephone number
`
`indicated below.
`
`Respectfully submitted,
`
`Date: 10/24/07
`
`/Joseph F. Posillico/
`
`Joseph F. Posillico
`Registration No. 32,290
`Synnestvedt & Lechner
`2600 Aramark Tower
`
`1101 Market Street
`
`Philadelphia, PA 19107
`Telephone: (215) 923-4466
`Facsimile: (215) 923-2189
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