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
Claims 1-15 of S. Dorok, et al., US 18/549,034 (09/05/2023) are pending. Claims 7-15 are withdrawn as directed to nonelected Groups. Claims 1-6 are under examination on merits and are rejected.
Election/Restrictions
Pursuant to the restriction requirement, Applicant elected Group I (claims 1-6), without traverse, in the reply filed on 04/06/2026. Claims 7-15 drawn to non-elected Groups (II)-(IV) are withdrawn from consideration pursuant to 37 CFR 1.142(b). The Restriction Requirement is made as Final.
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.
35 USC § 102 Rejection Over Becht
Claims 1-3 and 5 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by M. Becht, et al, 5(1), Chemistry of materials, 137-144 (1993)(“Becht”).
Becht teaches compound tetrakis[6,6,6-trifluoro-2,2-dimethyl-3,5-hexanedionato] cerium (Ce(fdh)4) with a structure as indicate below. Becht at page 137, paragraph 2, right col., line 2-3, structure of A; and page 138, left col., Experimental Section, Synthesis.
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Claims 1 and 5 are anticipated because each of the four ligands in the Becht compound Ce(fdh)4 can be regarded as
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that maps the general formula (II) in claim 1 as:
Y is CR3, wherein R3 is H;
R1 is CFRaRb, wherein both Ra and Rb are F; and
R2 is t-butyl.
Which meets each and every limitation of claims 1 and 5, therefore, claims 1 and 5 are anticipated.
Claim 2 is anticipated because the R1 (CF3) and R2 (t-butyl) in the Becht compound Ce(fdh)4 are different groups.
Claim 3 is also anticipated because each of the four ligands in the Becht compound Ce(fdh)4 also can be regarded as
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that maps the general formula (II) in claim 1 as:
Y is CR3, wherein R3 is H;
R2 is CFRaRb, wherein both Ra and Rb are F; and
R1 is t-butyl.
Which meets each and every limitation of claim 3, therefore, claim 3 is anticipated.
35 USC § 102 Rejection Over Zou
Claim 1 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Y. Zou, et al, CN111302926A (2020)(“Zou”). Zou is published in Chinese and a copy of machine translation is attached as the second part of the reference, which results in the total page of the full reference is 61. The format of citation of the reference is xx/61.
Zou teaches a compound having a structure as indicated below. Zou at page 10/61, left col. compound 30.
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The Zou compound 30 also can be drawn as follows
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The Zou compound 30 maps the formula (I) in claim 1 as L1-L4 are same, wherein, each of R1 and R2 is a C3 cycloalkyl, R3 is H (Y is CH); which meet each and every limitation of claim 1. Therefore, claim 1 is anticipated.
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.
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.
Claims 1-6 are rejected under 35 U.S.C. 103 as being unpatentable over Y. Zou, et al, CN111302926A (2020)(“Zou”).
Y. Zou, et al, CN111302926A (2020)(“Zou”)
Zou is published in Chinese and a copy of machine translation is attached as the second part of the reference, which results in the total page of the full reference is 61. The format of citation of the reference is xx/61.
Zou teaches a class of β-diketone cerium (IV) compounds represented by formula (I), which have a wide absorption band, are suitable for curing in the near-ultraviolet-visible light region, have high sensitivity, and are low-toxicity, cheap and easy; and the β-diketone cerium (IV) compounds can be used as a photoinitiator or photosensitizer.
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Zou at page 46/61, Summary of the invention and 14/61 for structure of the formula (I).
Regarding R1 and R3 of the formula (I), Zou teaches that:
R1 and R3 are the same or different, and are independently selected from C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C10 cycloalkyl, C6-C18 aryl, or include one or more selected from 5-10 membered heteroaryl groups of heteroatoms of N, S, and O, wherein each of the foregoing groups may be optionally substituted by one or more groups independently selected from the group consisting of halogen, nitro, . . . .
Zou at page 46/61, the last paragraph, emphasis added.
Zou teaches 83 example compounds such as compound 12 and compound 36, which has a chemical structure respectively as indicated below. Zou at page 11/61, Table, left col. compound 36 and page 24/61, [0118] for compound 12.
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After comparing of the structures of compound 12 and compound 36, one ordinary skilled artisan would be appraised that compound 36 is fluorine substituted product of the compound 12.
The Zou compound 36 also can be drawn as follows
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The Zou compound 36 maps the formula (I) in claim 1 as L1-L4 are same, wherein, of R1 is phenyl, R2 is CF3 and R3 is H (Y is CH).
Zou tested ultraviolet-visible light absorption spectrum of his 83 compounds and teaches that:
In addition, according to the ultraviolet-visible light absorption spectrum test, the absorption wavelength range of each of compounds 2-11, 13-17 and 19-83 is also in the range of 300-500nm, especially exhibiting good light absorption performance at 365-450nm. Moreover, the absorption intensity, that is, the molar extinction coefficient at the same wavelength, is far greater than Irgacure 784. Therefore, as a photoinitiator, the absorption spectra of compounds 2-11, 13-17, and 19-83 can also be well matched with the emission spectra of UV-LED light sources and have better photosensitivity.
Zou at page 59/61, the last paragraph, emphasis added.
Zou tested stability of his 83 compounds and teaches that:
In addition, the above stability experiment was repeated with each of compounds 2-17 and 19-83, and the results showed that the thermal stability of each of compounds 2-17 and 19-83 and the storage stability in the monomer were high. At 110°C. Therefore, the compounds 1-83 of the present invention have sufficient thermal stability and storage stability in acrylate monomers, and meet the requirements of ordinary light curing operations.
Zou at page 60/61, the last paragraph of Stability test, emphasis added.
Difference Between Zou compound 36 and the Claims 1-6
The Zou compound 36 differs from the instant claim 1 only in that the phenyl groups comprised in Zou compound 36 is not substituted by at least one radical selected from NO2, F, Cl, Br, CN, CF3, SF5, OCF3, SCF3, SO2CF3, N=C(CF3)2, and N(SO2CF3)2; however, Zou teaches that the aryl groups (R1 and/or R3) in the formula (I) can be substituted by one or more groups including halide. Zou at page 46/61, the last paragraph.
Rationales of Claims 1-6
Obviousness of a claimed compound can also be supported where there is motivation to substitute particular chemical moieties in a prior art compound for others so as to arrive at a claimed compound. MPEP § 2143(I)(B). For example, in the pharmaceutical arts, the rational is stated as motivation to select a known compound and also motivation to structurally modify the selected compound in a particular way to achieve a claimed compound. MPEP § 2143(I)(B) (see for example, MPEP § 2143(I)(B) Example 9, citing Eisai Co. Ltd. v. Dr. Reddy’s Labs., Ltd., 533 F.3d 1353, 87 USPQ2d 1452 (Fed. Cir. 2008).
One of ordinary skill is motivated to select one of Zou’s complexes such as the compound 36 for further investigation because Zou teaches it exhibits good light absorption performance at 365-450nm, it well matches with the emission spectra of UV-LED light sources and have better photosensitivity.
Having selected the Zou compound 36, one of ordinary skill is motivated to substitute hydrogen atoms of the phenyl groups with F atoms indicated below, thus arrived at the claimed first species at page 28 in claim 6, which meets each and every structural limitation of the general formula (I) in claims 1-6, therefore, claims 1-6 are obvious.
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One of ordinary skilled artisan is motivated to do so with a reasonable expectation of success because:
(i). Zou teaches that aryl group(s) in the compound 36 can be substituted by one or more halide; and
(ii) Per the structures of compound 12 and compound 36, Zou teaches that the halide can be F and the substitution can be perfluoro substitution.
The rationales supporting to elect the Zou compound 36 for modification is "obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success. MPEP 2143. I(E).
Non-Statutory Double Patenting Rejections
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).
Claims 1-6 are rejected on the ground of nonstatutory double patenting as being unpatentable over claim 9 of U.S. Patent No. 12,590,107B2 (2026). Although the claims at issue are not identical, they are not patentably distinct from each other because the conflicting claim 9 claims compound of formula (I.a).
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The species of R1 is 4-fluoro-3-trifluoromethyl)phenyl, R2 is pentafluoroethyl and R1 is H (see col. 67, table entry 8 of the conflicting claim) is the same compound of the claimed left second species at page 25 in claim 6, which meets each and every structural limitation of the general formula (I) in claims 1-6, therefore, claims 1-6 are anticipated.
Terminal Disclaimer
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.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to FRANK S. HOU whose telephone number is (571)272-1802. The examiner can normally be reached 6:30 am-2:30 pm Eastern on Monday to Friday.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at (571)2705241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/FRANK S. HOU/Examiner, Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
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