IN THE UNITED STATES PATENT AND TRADEMARK OFFICE
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`Docket No.: H0003965DlVlD
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`(PATENT)
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`In re Patent Application of:
`Rajiv R. Singh et al.
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`Application No.: |4;’225,588
`Attorney Docket: H0003965D1V1E
`Fi1ed:03/26/2014
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`Confirmation No.: 2681'‘
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`Art Unit: 1761
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`For: COMPOSITIONS CONTAINING FLUORINE
`SUBSTITUTED OLEFINS AND METHODS
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`Examiner: Hardee
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`AND SYSTEMS USING SAME
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`Electronically Filed
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`Mail Stop: Amendments
`Commissioner for Patents
`P. O. Box 1450
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`Alexandria, VA 22313-1450
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`RESPONSE TO OFFICE ACTION MAILED MAY 29, 2014
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`Dear Madam:
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`This is submitted in response to the Office Action having a mailing date of September 19,
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`2014, having a period for response set to expire on December 19, 2014. No fees are believed to be
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`required in connection with this communication. To the extent any other fee is required in
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`connection with the reply submitted herewith, please charge all such fees to Deposit Account No.
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`50-1943.
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`0 Amendments to the claims begin on page 2
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`0 Remarks begin on page 7.
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`AMENDMENTS TO THE CLAIMS
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`1. — 20. (Canceled)
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`21. (Currently amended)
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`A method for producing an automobile air conditioning system for
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`use with 2, 3, 3, 3-tetrafluoropropene (HFO-l234yt) comprising:
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`(a) providing an automobile vapor compression air conditioning system usable with refrigerant
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`l,l,l,2-tetrafluoroethane (HFC-134a") and having at
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`least one compressor and at
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`least one
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`Condenser; and
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`(b) providing a heat transfer composition in said system, said heat transfer composition consisting
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`essentially of:
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`(i) at least about 50% by Weight of a rCfris0rant
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`conditioning systems, said refrigerant consisting essentially of HFO- l234yf_', and
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`(ii) lubricant consisting essentially of polyalkylene glyeol(s), and
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`wherein (1) said condenser is operable with said refrigerant in a temperature range that includes
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`ISOOF and (2) said system when operating at a condenser temperature of ISDOF achieves a capacity
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`relative to HFC-134a of about 1 and a Coefficient of Performance (COP) relative to HFC-134a of
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`about 1.
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`22. (Previously presented)
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`The method of claim 21 wherein said lubricant is present in the heat
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`transfer composition in an amount of from about 30% to about 50% by weight.
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`23. (Previously presented)
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`The method of claim 21 wherein said HFO-l234yf is present in the
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`heat transfer composition in an amount of at least about 70% by weight.
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`24. (Previously presented")
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`The method of claim 21 wherein said refrigerant has no substantial
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`acute toxicity as measured by inhalation exposure to mice and rats.
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`25. (Previously presented)
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`The method of claim 24 wherein said refrigerant has a Global
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`Warming Potential (GWP) of not greater than about 150.
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`26. (Currently amended)
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`A method of conditioning the air
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`in an automobile using an
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`automobile air conditioning system including at least one compressor, at least one condenser and at
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`least one evaporator, said method comprising:
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`(a) utilizing in said system a heat transfer composition consisting essentially of:
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`(i) at least about 50% by weight of a refrigerant suitable for use in automobile air
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`conditioning systems. said refrigerant consisting essentially of 2, 3, 3, 3-tetrafluoropropene (HFO-
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`l234yt); and
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`(ii) lubricant consisting essentially of polyakylene glycol(s); and
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`(b) removing heat from said HFO-1234yf by condensing said refrigerant in said condenser when
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`said condenser is operating over a temperature range that that includes about l5U°F.
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`27. (Previously presented)
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`The method of claim 26 wherein said refrigerant achieves in said
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`system a capacity relative to HFC-134a of about 1 and a Coefficient of Performance (COP) relative
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`to HFC-134a of about 1.
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`28. (Previously presented)
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`The method of claim 26 wherein said lubricant is present in the heat
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`transfer composition in an amount of from about 30% to about 50% by weight.
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`29. (Previously presented)
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`The method of claim 2'? wherein said HFO-1234yf is present in the
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`heat transfer composition in an amount of at least about ?'0% by weight.
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`30. (Previously presented")
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`The method of claim 29 wherein said refrigerant has no substantial
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`acute toxicity as measured by inhalation exposure to mice and rats.
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`31. (Previously presented)
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`The method of claim 30 wherein said refrigerant has a Global
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`Warming Potential (GWP) of not greater than about 150.
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`32. (Currently amended)
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`A stable heat
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`transfer composition for use in an automobile air
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`conditioning system of the type having a condenser operating in a temperature range that includes
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`about l50°F, said heat transfer composition consisting essentially of:
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`(i) at least about 50% by weight of a low toxicity refrigerant suitable for use in automobile air
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`conditioning systems, said refrigerant consisting essentially of 2, 3, 3, 3-tetrafluoropropene (HFO-
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`l234yf)_; and
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`(ii) lubricant consisting essentially of polyakylene glycol(s),
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`wherein said refrigerant under the conditions of said condenser operating at about 150°F in said
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`automobile air conditioning system has a capacity relative to HFC-134a of about 1 and a Coefficient
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`of Performance (COP) relative to HFC-134a of about 1, and wherein said heat transfer composition
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`is stable in contact with aluminum, steel and copper.
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`33. (Previously presented)
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`The heat transfer composition of claim 32 wherein said heat transfer
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`composition has one liquid phase over the temperature range of from about -30°C to about +50°C.
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`34. (Previously presented)
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`The heat transfer composition of claim 32 wherein said lubricant is
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`present in the heat transfer composition in an amount of from about 30% to about 50% by weight.
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`35. (Previously presented)
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`The heat transfer composition of claim 32 wherein said HFO-1234yf
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`is present in the heat transfer composition in an amount of at least about 70% by weight.
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`36. (Previously presented)
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`The heat transfer composition of claim 35 wherein said refrigerant has
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`no substantial acute toxicity as measured by inhalation exposure to mice and rats.
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`37. (Previously presented)
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`The heat transfer composition of claim 36 wherein said refrigerant has
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`a Global Warming Potential (GWP) of not greater than about 150.
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`38. (Previously presented)
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`The heat transfer composition of claim 37 wherein said refrigerant
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`consists of HFO-1234yf.
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`39. (Currently amended)
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`A method for providing a system for cooling air in an automobile
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`comprising:
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`(a) providing in the automobile a vapor compression air conditioning system having at least one
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`compressor and at least one condenser; and
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`(b) providing in said system a heat transfer composition consisting essentially of:
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`(i) at least about 50% by weight of a low toxicity refrigerant suitable for use in automobile air
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`conditioning systems, said refrigerant consisting essentially of 2, 3, 3, 3-tetrafluoropropene (HFO-
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`l234yf); and
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`(ii) lubricant consisting essentially of polyakylene glycol(s), and
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`wherein (1) said condenser is operable with said refrigerant in a temperature range that includes
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`150013 and (2) said system operating at a condenser temperature of l50OF achieves a capacity
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`relative to HFC-134a of about 1 and a Coefficient of Performance (COP) relative to HFC-134a of
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`about 1.
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`40. (Previously presented)
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`The method of claim 39 wherein (A) said refrigerant has no
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`substantial acute toxicity as measured by inhalation exposure to mice and rats; (B) has a Global
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`Warming Potential (GWP) of not greater than about 150; and (C) said HFO-l234yf is present in the
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`heat transfer composition in an amount of at least about 70% by weight.
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`Reconsideration of the present application in view of the above amendments and following
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`REMARKS
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`remarks is respectfully requested.
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`1.
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`SUMMARY OF EXAMINER INTERVIEW
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`The undersigned conducted an in-person interview with the Examiner on December 17, 2014.
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`During the interview, possible presentation of additional amendments to the claims was proposed, and this
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`communication presents amendments to the claims along the lines discussed with the Examiner.
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`In
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`addition, a possible declaration by Dr. Singh was also discussed with the Examiner, and a Declaration
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`consistent with the points raised during the interview is filed concurrently herewith. The undersigned
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`expresses his gratitude for the helpful time and consideration of the Examiner during the interview.
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`I].
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`STATUS OF THE CLAIMS
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`As a result of this amendment, claims 21 — 40 are pending. Claims 2|, 26, 32 and 39 have
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`been amended to recite that the refrigerant is a low toxicity refrigerant suitable for use in automobile
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`air conditioning systems. Support for the amendments is found in the present specification, inter
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`alia, at page 11, lines 12 — 15 and page 6, lines 4, lines 8 — 18. No other claims have been amended.
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`No new claims are added and no claims are canceled.
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`III.
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`CLAIM REJECTIONS UNDER 35 USC 103
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`The Examiner has repeated the rejection of the claims as being obvious over JP 4-1 103 88 to Inagaki
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`(hereinafter “Inagaki”) in View of Bivens and as being obvious over RU 2,073,058 (hereinafter “RU058”)
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`in view of Bivens. The Examiner’s rejection of the claims is respectfully traversed.
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`IV.
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`SUMMARY OF THE CLAIMED SUBJECT MATTER
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`Claims 21 — 31 and 39 — 40 are directed to methods of producing or providing an automobile air
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`conditioning system (claims 21 — 25 and 39 - 40), or to conditioning the air in automobile by using an
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`automobile air conditioning system (claims 26 — 31). All of the methods and compositions require a heat
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`transfer composition in which the refrigerant is a low-toxicity refrigerant acceptable for use in
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`automobile air conditioning systems, and which consists essentially of 2, 3, 3, 3-tetrafluoropropene
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`(HFO- 1 234yf).
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`V.
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`THE OUTSTANDING REJECTION
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`In the outstanding office action the Examiner has acknowledged the prior arguments pointing out
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`that the claims are directed to the special field of automobile air conditioning and has indicated that the
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`argument may eventually provide a path to patentable subject matter. The items of information cited in the
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`prior office action in support of this position are provided to the Examiner with the IDS being filed
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`concurrently herewith. As mentioned in the prior office action, these items of information include a
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`detailed description of the essential requirements of automobile air-conditioning by an expert in the field of
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`automobile air-conditioning systems, Professor Denis Clodic, Professor at the Ecole des Mines de Paris and
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`Assistant Manager of the Centre for Energy Studies, in a Report dated December 1995.
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`Furthermore, the Examiner acknowledged that toxicity is a more important consideration in
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`automobile air conditioning that in other refrigeration applications. The Examiner suggested however that
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`the relevant toxicity information be submitted in the form of a separate declaration.
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`The Examiner has also discussed the use of the term “consisting essentially of” in connection with
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`the requirement of the refrigerant “consisting essentially of” HF()- l 234yf. The Examiner has stated the
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`position that applicants have the burden to establish what additional materials would change the basic and
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`novel characteristic of invention.
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`The amendments provided herein and the attached Singh Declaration are submitted in response to
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`the Examiner’s comments and are believed to adequately address those comments and place the present
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`application in condition for allowance, as explained in detail below.
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`VI.
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`THE CLAIMED SUBJECT MATTER IS PATENTABLE
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`A. Automobile Air Conditioning Is A Separate Field
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`The field of automotive air conditioning is a distinct technical field within the broader, general field
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`of heating and cooling applications, and as describe by Dr. Clodic in 1995 in the attached reports,
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`automobile air conditioning systems are special, in part, because they are mounted in the confined space
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`existing under the hood or bonnet of an automobile. As such, automotive air conditioning has specific
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`technical requirements as compared to other heating and cooling applications, including stationary air
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`conditioning, as explained in the response to the prior office action. Thus a person of ordinary skill in the
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`art would not simply expect that a material used as a refrigerant in applications other than automotive air
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`conditioning would be useful in automobile air conditioning.
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`Automobile air conditioning imposes very strict constraints directed to safety. This is because of
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`the unique configuration and environment of automobile air conditioning systems, including: i) close
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`proximity to the engine which typically contains gasoline or diesel, and ii) the air being circulated in a
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`small, confined, relatively sealed space containing humans, generally not encountered in other cooling and
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`heating applications. Thus, automobile air conditioning systems create specific toxicity constraints distinct
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`from and much more stringent than other heating and cooling applications.
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`B. HFO-l234yf Has Unexpectedly Low Toxicity
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`As mentioned in the response to the previous office action, the widely held belief in the art at the time ofthe
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`present invention was that fluorinated olefins were too toxic for use in an environment with potential exposure to the
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`consuming public. The unsaturated compound HFO-1225zc, which is within the Inagaki teachings, is consistent with
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`that belief in that testing of the toxicity of HFO-1225zc has led to the conclusion that it is unacceptable for
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`use as a refrigerant in automobile air conditioning applications. (See the declaration of Dr. Singh filed
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`concurrently herewith (hereinafter “Singh Declaration”) at paragraph 10). Testing of this compound by
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`DuPont has been published, revealing that HFO-l225zc has an acute toxicity, as measured by its LC 50, of
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`less than 2000 ppm. This makes HFO-1225zc approximately 200 times more toxic than HFO-l234yf
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`based on this measure of toxicity.
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`(Id; see also paragraph 7" for the toxicity of HFO-1234yfas measured by LC5o_
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`“No Observed Adverse Effect Level” (“NOAEL”) and Permissible Exposure Limit (“PEL”).
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`Another example ofthe relatively high toxicity of halogenated olefins as a class is 1, l , l-
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`trifluoropropene (HFO-1243zf). (Singh Declaration, paragraph 1 1). Toxicity testing on this
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`fluorinated olefin molecule has revealed that it will have NOAEL measure of toxicity that is less
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`than 5000 ppm.‘
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`(151). Thus, the toxicity of HFO- l243zf is at least an order of magnitude more
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`toxic than HFO-l234yf as measured by NOAEL, which means that based on the standards in place
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`at the time of the present invention, and still present today, it has been considered to be
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`unacceptable for use as a refrigerant in conventional automobile air conditioning applications.
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`(Ic.’.)
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`1 The testing on llFO—l2347.fdid not actually determine the NOAEL ofthat molecule. (Id) The testers determined only
`that the NOAHL would be less than 5000 ppm but further testing to determine the actual NOAIZL was not reported.
`(id)
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`These results establish that the low toxicity of HFO-1234yf is an important but unexpected
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`advantage of the invention as now claimed. (Singh Declaration, paragraph 13).
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`C. Low Toxicity Suitable for Automobile Air Conditioning Is A Basic and Novel Feature of
`the Invention as Claimed
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`A novel and basic feature of the invention as now claimed is the unexpected but advantageous low
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`toxicity of the selected refrigerant, as mentioned in the background of the present application as a necessary
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`property for many important applications. (Id.) For automobile air conditioning applications such as are
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`now being claimed, low toxicity of the refrigerant is of paramount concern because there is the potential in
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`such applications for refrigerant to leak into the small confined space of the passenger compartment of the
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`automobile during operation.
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`(Id., referencing page 2, line 30 — page 3, line 2 of the present application).
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`importantly, the present specification describes the finding that a careful selection of the fluorinated olefin
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`will result in a refrigerant composition that is capable of exhibiting “a highly desirable low level of
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`toxicity” and that the selection of a such a compound for use in refrigerant applications (among others) is of
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`“potentially enormous advantage” compared to refrigerants which would “...otherwise contain relatively
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`toxic compounds...” (Id, referencing page 6, lines 8 — 18 of the present application). One such compound
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`is HFO-1234yf as now claimed. Id.
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`The low toxicity property of HF()- l 234yf, and its acceptability for use in automobile air
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`conditioning is a “basic and novel” feature of the pending claims since those claims all relate to automobile
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`air conditioning applications for which the industry has established low toxicity criteria. (See Singh
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`Declaration, paragraph 14). Specifically, at the time of the present invention ASHRAE Standard 34 and the
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`SAE classified refrigerants according to their toxicity, with “A” being a lower degree of toxicity as
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`indicated by a “threshold limit value — time weighed average” (TLV-TWA) of 400 ppm or greater. (1d.)
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`As a consequence, in order to be acceptable for use in conventional automobile air conditioning at the time
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`of the present invention, a refrigerant must be Class A toxicity, that is, it must have a TLV-TWA (or a
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`PEL), greater than 400 ppm.
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`(151) The MSDS sheet for HFO-l234yf as sold by Honeywell indicates that
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`HFO-l234yf has a PEL of 500, thus establishing HFO-l234yf as a Class A refrigerant. Ud.)
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`Importantly, a person skilled in the art would be able to identify the materials, and the
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`concentrations of those materials, that would be excluded from the scope of the present claims by the
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`requirement that the refrigerant consists essentially of HFO-1234yf. This ability to understand the limiting
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`character of this requirement is based on fact that a novel and basic feature of the invention as now claimed
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`would be destroyed if a highly toxic substance was included in a refrigerant composition “consisting
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`essentially of’ HFO- I 234yf if such a compound were found in the refrigerant in an amount that would
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`make the TLV-TWA (or PEL) of the refrigerant fall below the limit considered acceptable for use in
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`conventional automobile air conditioning, namely, 400 ppm. (See Singh Declaration, paragraphs 15 and
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`16). By way of example, the person skilled in the art would be able to readily determine the maximum
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`amount of the fluorinated olefin hexafluoropropene (HFP) that could be included in a refrigerant consisting
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`essentially of HFO-1234yf. (hi) More specifically, given that HFP has a TLV-TWA of 0.1 ppm, the
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`maximum mole ratio of HFO- I 234yf:HFP in a binary refrigerant mixture would be 110005, or 50 ppm, in
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`order to ensure that the mixture does not exceed the 400 ppm PEL limit. (Id.) In other words, the claims
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`would literally exclude a refrigerant having more than about 50 ppm of HFP since such an amount would
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`render the refrigerant not acceptable for use in automobile air conditioning. The limits on any other
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`compound that might be present in a refrigerant could be similarly determined. (See Singh Declaration,
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`paragraph 17). Thus, the skilled person could readily determine the maximum amount of any such
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`compound that would take a refrigerant outside the requirement of “consisting essentially of HFO-l234yf.”
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`Ud.)
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`VI.
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`CONCLUSION
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`For all the reasons and evidence presented above, the present application is considered to be in
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`condition for allowance and early notice thereof is earnestly solicited.
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`Dated: December 19, 2014
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`Respectfully submitted,
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`By floseph F. Posillicox’
`Joseph F. Posillico
`Registration No.: 32,290
`FOX ROTHSCHILD LLP
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`100 Park Avenue
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`Suite 1500
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`New York, New York 10017
`(212) 878-7900
`(212)692-0940 (Fax)
`Attorneys!Agents For Applicant
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