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 .
DETAILED ACTION
This office action is in response to applicant’s communication filed on 2/11/26. Claims 1-25 are pending.
Applicant’s election without traverse of Group 1, claims 1-10 in the reply filed on 2/11/26 is acknowledged. Thus claims 11-25 are withdrawn from further consideration being drawn to the nonelected invention.
As a result, claims 1-10 are being examined in this Office Action.
Objections
Claim 1 is objected to because applicant recites “pentachlorocyclopropane (PCC) dissolved a first solvent” in claim 1. The examiner recommends “pentachlorocyclopropane (PCC) dissolved in a first solvent” for grammatical clarity.
Claim 3 is objected to because the claim recites duplicative members in the Markush group. Applicant recites “cyclohexylamine” twice and “2-amino-1-propanol” twice in the same group. The examiner recommends deleting the duplicate recitations.
Claim 7 is objected to because the claim recites “wherein the starred bond is to a carbon atom.” The star appears in the drawn chemical structure and the claim language depends on the symbol being clearly reproduced. Applicant should ensure that the chemical structure and the starred bond are clearly presented in the claim and drawings so that the metes and bounds of the claim can be determined.
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.
Claims 1-10 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 is indefinite because of the claim language “substantially soluble” and “substantially insoluble.”
The claim recites that the CPI-Cl salt is “substantially soluble” in the second solvent and the secondary amine salt is “substantially insoluble” in the second solvent. The specification does not appear to provide a clear standard for determining what amount of solubility qualifies as “substantially soluble” or what amount of residual solubility qualifies as “substantially insoluble”. Thus, one of ordinary skill in the art would not be reasonably apprised of the scope of the claim.
Claims 2-10 are rejected because they depend from rejected claim 1. Appropriate correction is required.
Claim Rejections – 35 USC 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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 of this title, 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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-7 and 10 are rejected under AIA 35 U.S.C. 103 as being unpatentable over Bandar et al. (“Structure-Activity Relationship Studies of Cyclopropenimines as Enantioselective Brønsted Base Catalysts,” Chem. Sci., 2015, 6, 1537-1547, and the associated supporting information), in view of Lambert et al. (US 20140288323, pub date Sep. 25, 2014; in applicant’s IDS filed 6/23/23), and further in view of Nichols, Lisa (Organic Chemistry Laboratory Techniques, “3.3F: Mixed Solvents,” Chemistry LibreTexts, derived from source content at organiclabtechniques.weebly.com; underlying textbook published 2016, with second edition made live July 8, 2017; retrieved from 3.3F: Mixed Solvents - Chemistry LibreTexts, is cited as evidence of the general knowledge of one of ordinary skill in the art regarding mixed-solvent purification/recrystallization).
Determination of the Scope and Content of the Prior Art
(MPEP §2141.01)
Bandar teaches a process for preparing cyclopropenimine compounds from pentachlorocyclopropane and amines. Bandar teaches adding dicyclohexylamine to a solution of pentachlorocyclopropane in dichloromethane, where a white precipitate forms during the reaction. Bandar teaches forming chloro[bis(dicyclohexylamino)]cyclopropenium chloride, filtering, washing, and washing the crude solid with hot ethyl acetate to yield the purified compound. Bandar further teaches reacting chloro[bis(dicyclohexylamino)]cyclopropenium chloride with a primary amine in the presence of N,N-diisopropylethylamine to form a cyclopropenimine hydrochloride salt, followed by recrystallization from a hot mixture of specified solvents. Bandar further teaches deprotonating the corresponding hydrochloride salt by dissolving the salt in dichloromethane and washing with 1.0 M NaOH to obtain the cyclopropenimine freebase. Bandar (Supporting Information, pp. 1-5, general scheme, “Chloro[bis(dicyclohexylamino)]cyclopropenium chloride (15),” “General procedure for cyclopropenimine hydrochloride salt synthesis,” “General procedure for cyclopropenimine hydrochloride deprotonation”)
Bandar also exemplifies cyclopropenimine hydrochloride salts and freebases prepared using primary amines, including amino alcohols, and teaches recrystallization from ethyl acetate/hexanes and ethyl acetate/hexanes/dichloromethane. Bandar (Supporting Information, Examples in pages 1-13).
Furthermore, Lambert teaches cyclopropenimine catalyst compositions and methods for making the same. Lambert teaches contacting a cyclopropene precursor with amines, including dicyclohexylamine and primary amines, to form cyclopropenimine salts and corresponding cyclopropenimine compounds. Lambert further teaches filtering, washing, drying, and use of aqueous base to obtain the cyclopropenimine. Lambert (Abstract, Figs. 6-9, paragraphs [0013]-[0021], [0062]-[0076], [0248]-[0256], and claims 7-11)
Additionally, the use of a mixed-solvent or solvent/antisolvent system to separate and purify compounds based on differential solubility is a routine purification technique in organic chemistry. In such a technique, a compound is dissolved in a solvent in which it is soluble, and a second solvent in which the compound or an impurity/byproduct has different solubility is used to induce precipitation, crystallization, or separation.
Nichols Chemistry LibreTexts teaches that mixed-solvent crystallization is a routine purification technique used when no single solvent satisfies the crystallization criteria, wherein a compound is dissolved in a “soluble solvent” and an “insoluble solvent” is added to reduce solubility and induce crystallization, with common solvent pairs including hexanes/ethyl acetate. (Nichols Chemistry LibreTexts, pages 1-2)
Ascertainment of the Difference Between Scope the Prior Art and the Claims
(MPEP §2141.012)
Together, Bandar and Lambert teach the process of forming cyclopropenimine compounds using chlorocyclopropene/pentachlorocyclopropane starting materials, secondary amines, including dicyclohexylamine, primary amines, cyclopropenium salt intermediates, and alkaline neutralization to obtain the corresponding cyclopropenimine.
However, Bandar and Lambert do not expressly teach the exact claim 1 solvent-separation step requiring that precipitated products are mixed in a second solvent wherein the CPI-Cl salt is substantially soluble and the secondary amine salt is substantially insoluble. Bandar and Lambert also do not expressly teach the exact solvent sequence recited in claim 4.
However, Bandar and Lambert teach filtering, washing, drying, hot-solvent washing, recrystallization, and isolation of cyclopropenium/cyclopropenimine salts, and Nichols Chemistry LibreTexts confirms that selection of solvent systems based on relative solubility is an ordinary purification technique.
Thus, because Nichols Chemistry LibreTexts teaches that mixed-solvent crystallization is a routine purification technique used when no single solvent satisfies the crystallization criteria, wherein a compound is dissolved in a “soluble solvent” and an “insoluble solvent” is added to reduce solubility and induce crystallization, the process of selecting a second solvent based on the relative solubilities of the desired CPI-Cl salt and undesired secondary amine salt would have been a routine purification/workup optimization to one of ordinary skill in the art.
Finding of Prima Facie Obviousness Rationale and Motivation
(MPEP §2142-2143)
Therefore, it would have been obvious to one of ordinary skill in the art at the time the invention was made to modify the process of Bandar with the teachings of Lambert to obtain the claimed process for forming a cyclopropenimine because both references are directed to the same field of cyclopropenimine and cyclopropenium chemistry, both teach preparing cyclopropenimine compounds from chlorocyclopropene starting materials and amines, both teach dicyclohexylamino-substituted cyclopropenimine species, and both teach conversion of cyclopropenimine salts to neutral cyclopropenimine compounds.
It would further have been obvious to one of ordinary skill in the art to select a solvent or mixed-solvent system based on the relative solubilities of the desired cyclopropenium/CPI salt and undesired amine salt byproducts. The use of a solvent/antisolvent or mixed-solvent system to dissolve a desired compound while leaving an impurity or byproduct insoluble, or to precipitate/recrystallize a desired compound from solution, is a routine purification technique in organic chemistry.
Thus, selecting a second solvent in which the desired CPI-Cl salt is soluble and the secondary amine salt is insoluble would have been no more than routine optimization of the known Bandar/Lambert workup, which already teaches filtering, washing, drying, hot-solvent washing, recrystallization, and isolation of cyclopropenium/cyclopropenimine salts.
It would also have been obvious to select the claimed primary amines because the prior art teaches modular installation of the imino substituent by reaction of the cyclopropenium chloride intermediate with a primary amine. Bandar teaches general reaction of chloro[bis(dicyclohexylamino)]cyclopropenium chloride with selected amines and provides amino alcohol examples. Lambert also teaches amines useful in cyclopropenimine formation. The selection of one known primary amine for another in the same known reaction would have been a predictable use of prior art elements according to their established functions.
Therefore, the subject matter of claims 1-7 and 10 would have been obvious over Bandar in view of Lambert and further in view of Nichols Chemistry LibreTexts.
Claims 8-9 are rejected under AIA 35 U.S.C. 103 as being unpatentable over Bandar et al. (“Structure-Activity Relationship Studies of Cyclopropenimines as Enantioselective Brønsted Base Catalysts,” Chem. Sci., 2015, 6, 1537-1547, and the associated supporting information), in view of Lambert et al. (US 20140288323, pub date Sep. 25, 2014; in applicant’s IDS filed 6/23/23), and further in view of Lambert 2018 et al. (US 20180215847, pub date Aug. 2, 2018).
Determination of the Scope and Content of the Prior Art
(MPEP §2141.01)
Bandar teaches a process for preparing cyclopropenimine compounds from pentachlorocyclopropane and amines. Bandar teaches adding dicyclohexylamine to a solution of pentachlorocyclopropane in dichloromethane, where a white precipitate forms during the reaction. Bandar teaches forming chloro[bis(dicyclohexylamino)]cyclopropenium chloride, filtering, washing, and washing the crude solid with hot ethyl acetate to yield the purified compound. Bandar further teaches reacting chloro[bis(dicyclohexylamino)]cyclopropenium chloride with a primary amine in the presence of N,N-diisopropylethylamine to form a cyclopropenimine hydrochloride salt, followed by recrystallization from a hot mixture of specified solvents. Bandar further teaches deprotonating the corresponding hydrochloride salt by dissolving the salt in dichloromethane and washing with 1.0 M NaOH to obtain the cyclopropenimine freebase. Bandar (Supporting Information, pp. 1-5, general scheme, “Chloro[bis(dicyclohexylamino)]cyclopropenium chloride (15),” “General procedure for cyclopropenimine hydrochloride salt synthesis,” “General procedure for cyclopropenimine hydrochloride deprotonation”)
Bandar also exemplifies cyclopropenimine hydrochloride salts and freebases prepared using primary amines, including amino alcohols, and teaches recrystallization from ethyl acetate/hexanes and ethyl acetate/hexanes/dichloromethane. Bandar (Supporting Information, Examples in pages 1-13).
Furthermore, Lambert teaches cyclopropenimine catalyst compositions and methods for making the same. Lambert teaches contacting a cyclopropene precursor with amines, including dicyclohexylamine and primary amines, to form cyclopropenimine salts and corresponding cyclopropenimine compounds. Lambert further teaches filtering, washing, drying, and use of aqueous base to obtain the cyclopropenimine. Lambert (Abstract, Figs. 6-9, paragraphs [0013]-[0021], [0062]-[0076], [0248]-[0256], and claims 7-11)
Thus, Bandar and Lambert teach the cyclopropenimine/cyclopropenium salt chemistry discussed above, including formation of cyclopropenimine hydrochloride/trisaminocyclopropenium-type salts and alkaline neutralization to obtain the corresponding neutral cyclopropenimine freebase.
Additionally, Lambert 2018 teaches cyclopropenium polymers and methods for making the same. Lambert 2018 teaches processes for incorporating a cyclopropenium ion into a polymeric system, including processes for making cross-linked polymers, linear polymers, dendritic polymers, and for incorporating a cyclopropenium ion onto a preformed polymer. Lambert 2018 teaches polyelectrolytes from cyclopropenium cation building blocks, including homopolymers, block copolymers, statistical copolymers, and nanoparticles, made by reversible-deactivation radical polymerization and emulsion polymerization. Lambert 2018 (Abstract, Figs. 1 and 4-6, paragraphs [0002]-[0014], [0027]-[0034], [0050]-[0065], and [0070]-[0093])
Lambert 2018 further teaches cyclopropenium monomers bearing polymerizable units. Lambert 2018 teaches that a functionalized cyclopropenium ion may be contacted with a polymerizing agent under conditions suitable to react and form a linear polymer comprising a stable cyclopropenium cation. Lambert 2018 also teaches polymerizing agents including radical initiators and RAFT agents, and expressly identifies AIBN. Additionally, Lambert 2018 provides reaction schemes in which cyclopropenium monomers are polymerized using AIBN/DMF to form homopolymers, block copolymers, and random copolymers. Lambert 2018 (Figs. 4-6, paragraphs [0078]-[0093], [0118]-[0129], and claims 1, 17, and 19)
Furthermore, Lambert 2018 teaches synthesis of cyclopropenium ions from tetrachlorocyclopropene with secondary amines, including dicyclohexylamine, and further reaction with another amine to obtain cyclopropenium ions. Lambert 2018 (paragraphs [0248]-[0256])
Ascertainment of the Difference Between Scope the Prior Art and the Claims
(MPEP §2141.012)
Together, the combination of Bandar and Lambert teaches forming cyclopropenimine salts and neutralizing the salts with alkaline solution to obtain neutral cyclopropenimine freebase. Lambert 2018 teaches polymerizing cyclopropenium salt monomers bearing polymerizable functionality to form cyclopropenium-based polymers.
But, the prior art does not expressly teach applicant’s exact sequence of polymerizing the specific TAC salt obtained from the exact claim 1 process and thereafter neutralizing the TAC salt polymer to obtain CPI pendent groups.
However, Lambert 2018 teaches that cyclopropenium salt monomers bearing polymerizable functionality are useful for polymerization into cyclopropenium-based polymers, while Bandar and Lambert teach that cyclopropenimine/cyclopropenium salt functionality may be converted to the corresponding neutral cyclopropenimine by alkaline treatment.
Finding of Prima Facie Obviousness Rationale and Motivation
(MPEP §2142-2143)
Therefore, it would have been obvious to one of ordinary skill in the art at the time the invention was made to further modify the process of Bandar and Lambert with the teachings of Lambert 2018 to polymerize a TAC/cyclopropenium salt having a polymerizable substituent and then neutralize the resulting salt polymer to obtain CPI pendent groups.
One of ordinary skill in the art would have been motivated to make the modification because Lambert 2018 expressly teaches cyclopropenium polymers and methods for making the same, including cyclopropenium monomers having polymerizable units, and teaches forming homopolymers, block copolymers, random copolymers, and nanoparticles from cyclopropenium cation building blocks. Thus, one of ordinary skill in the art would have had reason to incorporate a polymerizable amine substituent into the known Bandar/Lambert cyclopropenium/TAC salt scaffold and polymerize the resulting salt using known polymerization techniques, such as radical polymerization, RAFT polymerization, or emulsion polymerization.
One of ordinary skill in the art would have had a reasonable expectation of success because Lambert 2018 teaches successful synthesis and polymerization of cyclopropenium monomers and teaches that such cyclopropenium-containing polymers retain stable cyclopropenium cation functionality. Further, Bandar and Lambert teach alkaline conversion of the corresponding cyclopropenimine/cyclopropenium salt to the neutral cyclopropenimine freebase. Applying the known alkaline neutralization to the same cyclopropenimine/cyclopropenium salt functionality after polymerization would have been a predictable use of the same acid-base chemistry to obtain CPI pendent groups on a polymer backbone.
Therefore, the subject matter of claims 8-9 would have been obvious over Bandar in view of Lambert and further in view of Lambert 2018.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jennifer Cho Sawyer whose telephone number is (571) 270 1690. The examiner can normally be reached on Monday-Friday 9 AM - 6 PM PST.
If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Renee Claytor can be reached on (571) 272-8394. The fax phone number for the organization where this application or proceeding is assigned is 571-274-1690.
Information regarding the status of an application may be obtained from the Patent Application Information Retrieval (PAIR) system. Status information for published applications may be obtained from either Private PAIR or Public PAIR. Status information for unpublished applications is available through Private PAIR only. For more information about the PAIR system, see http://pair-direct.uspto.gov. Should you have questions on access to the Private PAIR system, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative or access to the automated information system, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
Jennifer Cho Sawyer
Patent Examiner
Art Unit: 1691
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691
Prosecution Insights