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 responsive to Applicant's preliminary amendments filed April 18, 2024. As filed, claims 1-15 are pending.
Priority
This application, filed 04/18/2024 is a National Stage entry of PCT/EP2022/078762 , International Filing Date: 10/17/2022 claims foreign priority to 21203092.8, filed 10/18/2021.
Information Disclosure Statement
Applicants' information disclosure statements (IDS) filed have been considered except where lined through. Please refer to Applicants' copy of the 1449 submitted herewith. Claim Objections
Claims 1, 14, 15 recite the “using” language. The objected claim is not viewed as “use” claim, but proper transition wording should be present.
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 (i.e., changing from AIA to pre-AIA ) 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, 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 text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
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.
1.Claims 1-13 are rejected under 35 U.S.C. 103 as being unpatentable over US US 3 342 854 Sept. 19, 1967 (“the ‘854 patent”; cited by Applicants in IDS) and further in view of US 3 227 745 (“the ‘745 patent”; cited by Applicants in IDS).
The claims are drawn to a process for producing a dimer according to formula (II)
comprising a step i) of dimerization of alkyl acrylates according to formula (I) to obtain a
dimer according to formula (II) using a catalyst according to formula (III)
PNG
media_image1.png
200
400
media_image1.png
Greyscale
and wherein said step i) of dimerization is performed in presence of a compound A being
a tertiary alcohol or a silanol.
Regarding instant claims 1, 4-5, the ‘854 patent teaches a process for producing discloses a dimerization of ethyl acrylates which corresponds to claimed formula (I) in which variable R is ethyl to obtain the dimer diethyl 2-methyleneglutarate which corresponds to claimed formula (II) when variable R is ethyl. The process of the ‘854 patent teaches the reaction conducted under catalyst Ph-P(NEt2)2, which corresponds to claimed formula (Ill) wherein Ra is phenyl (hydrocarbyl), Rb is NR3R4 and R1 to R4 are ethyl (aliphatic group). The isolated yield of the dimer product diethyl 2-methyleneglutarate which corresponds to claimed formula (Il) after distillation is 328 g (82 %) ( col 1 1 lines 10-70; example 2 col 3).
Regarding instant claim3, the amount of catalyst used is about 1 mol% (based on 7.1 g dichlorophenyl phosphine and 400 g ethyl acrylate), that is about 0.01 molar equivalents (example 2).
Regarding instant claims 6-9, the ‘854 patent teaches that the catalyst for dimerization of either formula I or II
PNG
media_image2.png
200
400
media_image2.png
Greyscale
PNG
media_image3.png
200
400
media_image3.png
Greyscale
Regarding instant claim 10, the ‘854 patent teaches benzene as organic solvent (example 2).
Regarding instant claim 11, the ‘854 patent teaches the reaction at 25C for 2h. (example 2).
Regarding instant claims 12 and 13, the ‘854 patent teaches that the catalyst is prepared in a step preceding the dimerization by reacting dichlorophenyl phosphine which corresponds to claimed formula (IV) in which X and Rc are each chlorine and Ra is phenyl) and diethyl amine which corresponds to claimed formula (V) in which R1 and r2 are each ethyl.
The method of the present application differs from the method described in the ‘854 patent in that prior art does not disclose the reaction conducted in tertiary alcohol or silanol.
However, the ‘745 patent, analogous prior art, drawn to the same reaction as the ‘854 patent – dimerization of alkyl acrylates teaches that alcohol solvents, such as tertiary butyl alcohol, in addition to serving as reaction media may participate in the reaction process by supplying available hydrogen ions which serve to minimize the production and that further that the use of hydroxylic solvents enables the dimerization
process to be conducted at temperatures higher than when aprotic solvents are employed while retaining a greater selectivity for dimerization and that propagation of the reactant chains that result in the production of polymeric product is prevented (col 1, line 58 -70 continuing on col 2, line 1-12).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention, to combine the teachings of the ‘854 patent regarding preparation of dimers by dimerization reaction of alkyl acrylates mediated by catalyst with the teachings of the ‘745 patent regarding utilizing tertiary alcohol for dimerization of alkyl acrylates including t-butanol, and have reasonable expectation of success in arriving at the claimed invention, because the prior art teach that the use of hydroxylic solvents enables the dimerization process to be conducted at temperatures higher than when aprotic solvents are employed, and yet retain greater selectivity for dimerization and the formation of polymeric byproducts is avoided.
"Exemplary rationales that may support a conclusion of obviousness include: (A) Combining prior art elements according to known methods to yield predictable results ". See MPEP § 2143.
Thus, the instant claims are obvious over the combined teachings of prior art.
2.Claims 1-14 are rejected under 35 U.S.C. 103 as being unpatentable over US US 3 342 854 Sept. 19, 1967 (“the ‘854 patent”; cited by Applicants in IDS) and US 3 227 745 (“the ‘745 patent”; cited by Applicants in IDS) and applied to claims 1-13 above and further in view of Borszeky et al. Tetrahedron Asymmetry, 1997, No. 22, pp. 3745-3753 (cited in PTO892 attached herewith).
The combined teachings of ‘864 and ‘745 patent regarding claims 1-13 are discussed above.
The cited references do not teach the step of hydrogenation of the dimer to the claimed formula (VI) of instant claim 14.
However, the article by Borszeky teaches aspect of hydrogenation of unsaturated substrates ( Table 1 page 3747; experimental) with hydrogen, mediated by Pd catalyst.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention, to combine the teachings of the cited prior art and have reasonable expectation of success in arriving at the claimed invention.
The rationale to support a conclusion that the claim would have been obvious is that 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_, 82 USPQ2d at 1395.
Therefore, the claimed invention as a whole is prima facie obvious over the combined teachings of the prior art.
3.Claims 1-13, 15 are rejected under 35 U.S.C. 103 as being unpatentable over US US 3 342 854 Sept. 19, 1967 (“the ‘854 patent”; cited by Applicants in IDS) and US 3 227 745 (“the ‘745 patent”; cited by Applicants in IDS ) and applied to claims 1-13 above and further in view of US 342853, 1967 cited by Applicants in IDS).
The combined teachings of ‘864 and ‘745 patent regarding claims 1-13 are discussed above.
The cited references do not teach the step of hydrolysis of the dimer to the claimed formula (VII) of instant claim 15.
However, the ‘853 patent, analogous prior art also drawn to preparation of dimers from alkyl acrylates, teach the hydrolysis of dimes to corresponding carboxylic acid compounds (examples on col 3-4).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention, to combine the teachings of the cited prior art and have reasonable expectation of success in arriving at the claimed invention.
The rationale to support a conclusion that the claim would have been obvious is that 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_, 82 USPQ2d at 1395.
Therefore, the claimed invention as a whole is prima facie obvious over the combined teachings of the prior art.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-15 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-20 of copending Application No. 19/475.038 Although the claims at issue are not identical, they are not patentably distinct from each other because the both claim the same process for producing a dimer according to formula (II)comprising a step i) of dimerization of alkyl acrylates according to formula (I) to obtain a dimer according to formula (II) using a catalyst according to formula (III).
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Conclusion
Claims 1-15 are rejected.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ANA MURESAN whose telephone number is (571)-270-7587. The examiner can normally be reached on Monday through Friday, 8:30 am to 5:30 pm EST.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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.
/ANA Z MURESAN/ Primary Examiner, Art Unit 1692
