DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Status of the Claims
Claims 1 – 14 are pending and rejected.
Priority
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Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Information Disclosure Statement
The information disclosure statements (IDS) submitted on August 21, 2024 and June 18, 2025 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Claim Objections
Claims 1 and 13 is objected to because of the following informalities:
Claim 1, line 5 of the claim: Insert the term “wherein” before the limitation “in Formula 1”.
Claim 13, lines 3-4 of the claim: The limitation “… performed under water; at least one polar organic solvent selected from… ether, and ester; or a mixture thereof” is grammatically incorrect because it contains an incomplete sentence after the semi-colon (;). In order to overcome the objection, Applicant may amend to replace the semi-colon (;) with a comma (,) and a conjunction “or” as follows: “… performed under water[[;]], or at least one polar organic solvent selected from… ether, and ester; or a mixture thereof”.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
Claim 1 – 14 are rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor, regards as the invention.
Claim 1 recites the limitation of hydrogen carbonate “(MHCO3)”. See, line 3 of the claim. However, claim 1 does not explicitly recite the limitations associated with the variable “M” in the hydrogen carbonate. Thus, the metes and bounds of the claim are not properly defined and a person having ordinary skill in the art cannot ascertain the scope of the instant claim. Therefore, the claim is indefinite. Further, dependent claims 2 – 14 do not clarify or cure the deficiencies in claim 1 and are also considered indefinite.
In order to overcome the rejection, Applicant may amend claim 1 to specifically define the scope of variable “M”.
Claim 3 is rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor, regards as the invention.
Claim 3 recites the limitation (see, lines 4-5 of the claim) (Emphasis added):
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However, claim 3 does not explicitly recite the limitations associated with the variables “M+” and “HCO3–”. Thus, the metes and bounds of the claims are not properly defined and a person having ordinary skill in the art cannot ascertain the scope of the instant claim. Therefore, the claim is indefinite.
In order to overcome the rejection, Applicant may amend claim 3 to incorporate the limitations of claims 4 and 14.
Claims 4 and 14 are rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor, regards as the invention.
Claim 4 recites the limitation “… synthesizing alkylene carbonate of claim 2, wherein, in Scheme 1, metal (M+) is selected from…”. Emphasis added. See, page 1, lines 1-2 of the claim. However, claim 2 (or ultimately, independent claim 1) upon which claim 4 is dependent upon, does not explicitly recite the limitations of Scheme 1. There is insufficient antecedent basis for this limitation in the claim.
In order to overcome the rejection, Applicant may amend claim 4 to be dependent upon claim 3.
Similarly, claim 14 recites the limitation “… synthesizing alkylene carbonate of claim 1, wherein the hydrogen carbonate ion (HCO3–) is obtained by reacting…”. Emphasis added. See, lines 1-2 of the claim. However, claim 1 upon which claim 14 is dependent upon, does not explicitly recite the limitations of the hydrogen carbonate ion (HCO3–). There is insufficient antecedent basis for this limitation in the claim.
In order to overcome the rejection, Applicant may amend claim 14 to be dependent upon claim 3.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1 – 8 and 13 are rejected under 35 U.S.C. 102(a)(1)/102(a)(2) as being anticipated by Steimmig et al. US 1,907,891 A, cited in IDS dated August 21, 2024.
Steimmig et al. teach a process of reacting 1000 parts of 40% aqueous solution of ethylene chlorohydin (also known as chloroethanol) (40 parts of ethylene chlorohydrin and 60 parts of water), with 200 parts of sodium bicarbonate (NaHCO3). The mixture is heated at 60° to 70° C, and distilled in vacuo. See, e.g., Example 3.
The prior art anticipates the instant claims as presented below:
With respect to claims 1, 3, 5 and 13, Steimmig teaches a method comprising mixing a compound represented by the following Formula 1, which is a liquid (40% aqueous solution of ethylene chlorohydin) (40 parts of ethylene chlorohydrin and 60 parts of water (solvent)) with sodium bicarbonate (NaHCO3),
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, wherein in Formula 1:
X is chlorine, and
R1 and R2 are each hydrogen.
Please note that the limitation “for synthesizing alkylene carbonate” is an intended use limitation as governed by MPEP §2111.02(II). Intended use limitations are interpreted based on the structural limitations they impart to the invention. In this case, the intended use only requires the method is capable for synthesizing alkylene carbonate, but does not impart any specific structural limitations. Based on the teachings of Steimmig et al., the method is capable for synthesizing alkylene carbonate.
Claim 2, wherein sodium bicarbonate is solid form.
Claim 4, wherein metal is sodium (Na+) (alkali metal cation).
Claim 6, wherein the mixing operation is performed at a temperature of 60° to 70° C.
With respect to claim 7, Steimmig et al. teach reacting 1000 parts of 40% aqueous solution of ethylene chlorohydin (40 parts of ethylene chlorohydrin and 60 parts of water), which is 1000 parts x (40/100) = 400 total parts of ethylene chlorohydrin. Steimmig also teaches 200 parts of sodium bicarbonate. Thus, ethylene chlorohydrin and sodium bicarbonate are mixed in a molar ratio of 1:0.5.
Regarding claim 8, Steimmig et al. teaches the mixing operation is performed under atmospheric pressure conditions. See, e.g., page 1, 2nd paragraph.
Claims 1 – 5, 8 and 13 – 14 are rejected under 35 U.S.C. 102(a)(1)/102(a)(2) as being anticipated by Venturello et al. US 4,226,778 A, cited in IDS dated August 21, 2024.
Venturello et al. teach a process of mixing a suspension of tetramethyl-ammonium bicarbonate (in methanol solution) with ethylene bromohydrin (also known as bromoethanol) at a temperature of 20 °C and in carbon dioxide atmosphere. The mixture was separate by filtration, washed and distilled under vacuum to obtain the final product. See, e.g., Example 1.
The prior art anticipates the instant claims as presented below:
With respect to claims 1, 3, 5 and 13, Venturello teaches a method comprising mixing a compound represented by the following Formula 1, which is a liquid, with tetramethyl-ammonium bicarbonate ((N(CH3)4+ HCO3–),
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, wherein in Formula 1:
X is bromine, and
R1 and R2 are each hydrogen.
Please note that the limitation “for synthesizing alkylene carbonate” is an intended use limitation as governed by MPEP §2111.02(II). Intended use limitations are interpreted based on the structural limitations they impart to the invention. In this case, the intended use only requires the method is capable for synthesizing alkylene carbonate, but does not impart any specific structural limitations. Based on the teachings of Venturello et al., the method is capable for synthesizing alkylene carbonate.
Claim 2, wherein tetramethyl-ammonium bicarbonate is solid form.
Claim 4, wherein metal is quaternary ammonium (tetramethyl-ammonium).
With respect to claim 8, Steimmig et al. teaches the mixing operation is performed under atmospheric pressure conditions. See, e.g., Examples 1-2.
With respect to claim 14, Steimmig et al. teaches the bicarbonate is obtained by reacting quaternary ammonium hydroxide with carbon dioxide in the presence of a dilute solution. See, e.g., column 3, lines 50-58. Steimmig further teaches “[w]hen bicarbonates of resins are used as carbonating agents for the halohydrins, aqueous-organic mixtures, such as water-dioxane, water acetonitrile, and the like, may be employed as well as a solvent… [i]In some particular cases, even water alone may be used”. See, e.g., column 2, lines 56-61.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
Claims 9 – 12 are rejected under 35 U.S.C. 103 as being unpatentable over Steimmig et al. US 1,907,891 A, as applied to claims 1 – 8 and 13 above, in view of Yadav et al., Tetrahedron Letters 46 (2005), pp. 3569 – 3572, cited in IDS dated August 21, 2024.
Determining the scope and contents of the prior art
Steimmig et al. teach a process of reacting 1000 parts of 40% aqueous solution of ethylene chlorohydin (also known as chloroethanol) (40 parts of ethylene chlorohydrin and 60 parts of water), with 200 parts of sodium bicarbonate (NaHCO3). The mixture is heated at 60° to 70° C, and distilled in vacuo. See, e.g., Example 3.
Stemmig does not teach the method of obtaining the compound represented by Formula 1, as recited in claims 9 – 12.
Yadav et al. teach a process of halogenating olefins using N-halosuccinimides and [bmim]BF4/water system in order to synthesize bromohydrins. Yadav teaches that [bmim]BF4/water system is an “efficient alternative for the synthesis of bromo- and iodohydrins from alkenes and N-bromo and N-iodosuccinimides”. The process comprises “simple experimental and product isolation procedures combined with east of recovery and reuse of this novel reaction media” and the use of ionic liquids avoids “the use of environmentally unfavourable organic solvents. See, e.g., pp. 3571, 2nd paragraph.
Ascertaining the differences between the prior art and the claims at issue
Compared to claim 9, Stemmig does not teach the process of mixing alkylene compounds (ethylene or propylene) with halogen-substituted nitrogen compound (N-bromosuccinimide (NBS)) to prepare instant compound represented by Formula 1.
Rationale for a prima facie case of obviousness
According to MPEP §2141(III), two of the rationales in the KSR decision states “(C) Use of known technique to improve similar devices (methods, or products) in the same way…
(G) Some teaching, suggestion, or motivation in the prior art that would have led one of ordinary
skill to modify the prior art reference or to combine prior art reference teachings to arrive at the
claimed invention”. KSR, 550 U.S. at 418, 82 USPQ2d at 1396. Yadav specifically teaches mixing 1 mmol alkene and 1.2 mmmol N-bromosuccinimide (NBS) in [bmim]BF4/water system, extracting and concentrating the reaction mixture in vacuo in order to obtain bromohydrins. See, e.g., pp. 3570, Table 1, and pp. 3572, point (11). The synthesis is presented below (see, e.g., pp. 3570, Scheme 1):
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A person having ordinary skill in the art would have been motivated to employ the use of alkenes in the same known process as described by Yadav et al. to synthesize bromohydrins because similar results would be obtained from similar alkylene or alkene compounds. The PHOSITA would have performed routine experimentation, such as combining the process of preparing bromohydrins (as taught by Yadav et al.) with the process of using said bromohydrins to further synthesize the final alkylene carbonates (as taught by Stemmig et al.). The purpose of the routine experimentation would have been to optimize the reaction steps, and remove any additional reactants and reagents, in order to assess and improve the efficiency of the processes. The PHOSITA would have also been motivated to decrease the amount of impurities in the final alkylene carbonates by preventing any unnecessary additional reactions with the solvents and/or reactants. Therefore, the combined teachings of the prior art render the instant claim prima facie obvious.
With respect to claims 10 – 12, Yadav teaches that the same nitrogen compound, N-bromosuccinimide (NBS), as claimed in the claims. MPEP 2112.01 Sections (I) – (II) states:
“Where the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977)”.
Since Yadav et al. teach the same nitrogen compound, the compound would inherently possess the same pKa of 7 to 14 of conjugate acid of the nitrogen compound.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Sagar Patel whose telephone number is (571)272-1317. The examiner can normally be reached Monday - Friday: 9am to 5pm EST.
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/Sagar Patel/Examiner, Art Unit 1626
/KAMAL A SAEED/Primary Examiner, Art Unit 1626
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