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
The amendment filed on 11/04/2025 has been entered. Claims 1-14 have been amended and are currently pending and are under examination.
Withdrawn Objections and Rejections
Claims 1 and 7-8 have been amended to obviate the minor informalities and thus the objection has been withdrawn.
The 112(b) rejection has also been withdrawn in view of Applicant’s persuasive arguments.
Upon further consideration, the examiner notes that copending Application No. 18/064,955 recites a compound of formula (1) that is different from the instantly claimed formula (1) of the instant claim1. Thus, the nonstatutory double patenting rejection over the claims of the copending Application No. 18/064,955 has been withdrawn.
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.
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Claims 1-14 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-11 of copending Application No. 18/345,462 in view of Patent number CN102795978A (CN’978; cited in IDS 05/03/2024 and machine translation attached herein).
The claims at issue are drawn to a process for preparing aldehydes using the same process steps that comprise:
a) initially charging an olefin;
b) adding a compound of formula (I):
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where R1, R2, R3, R4, R5, R6, R7, R8 are selected from: —H, —(C1-C12)-alkyl, -Ph;
c) adding a Pt compound capable of forming a complex;
d) adding an iodine compound;
e) feeding in CO and H2;
f) heating the reaction mixture from steps a) to e), to convert the olefin to an aldehyde.
Copending claim 1 of Application No. 18/345,462 recites the conversion of vinylcyclohexene to dialdehyde. Copending claim 1 of Application No. 18/064,955 recites the conversion of the generic olefin to aldehyde. However, the copending claims fail to recite the conversion of dicyclopentadiene to dicidal
The deficiency is cured by CN’978.
CN’978 teaches that tricyclodecane dicarbaldehyde (dicidal) plays a big role as an intermediate for the preparation of tricyclodecane dimethanol (dicidol), an important chemical raw material. The reference teaches that the unsaturated amorphous polyester resin composite material developed from tricyclodecane dimethanol, which is free of benzene and formaldehyde, has the characteristics of anti-yellowing and low viscosity, and has been widely used in water-based dispersions, coating compositions, lubricating oils, etc. CN’978 further teaches the use of a two-stage process and a different catalyst in the production of tricyclodecane dicarbaldehyde from dicyclopentadiene.
In accordance to MPEP 2143, the Supreme Court in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) identified a number of rationales to support a conclusion of obviousness which are consistent with the proper “functional approach” to the determination of obviousness as laid down in Graham and discussed circumstances in which a patent might be determined to be obvious. In this case, at least prong (B) simple substitution of one known element for another to obtain predictable results applies.
In this instance, using the catalyst and process steps of the copending claim in place of the two-stage process and catalyst of CN’978, a skilled artisan has a reasonable expectation in arriving at the instantly claimed process, which yields nothing more than the predictable dicidol product from dicyclopentadiene. Furthermore, in view of the teachings of CN’978 about the importance of synthesizing dicidol, a skilled artisan would have been motivated to use dicyclopentadiene as an olefin starting compound of the copending claims with a reasonable expectation of success in obtaining dicidol.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct instantly claimed process in the conversion of dicyclopentadiene to dicidol in view of the combination of copending claims and CN’978.
This is a provisional nonstatutory double patenting rejection.
Claims 1-14 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-15 of U.S. Patent No. 11,773,042B2 (‘042-I), over claims 1-15 of U.S. Patent No. 11,739,042B2 (‘042-II), or over claims 1-15 of U.S. Patent No. 11,866,400B2 (‘400) in view of Patent number CN102795978A (CN’978; cited in IDS 05/03/2024 and machine translation attached herein).
The claims at issue are drawn to a process for preparing aldehydes using the same process steps that comprise:
a) initially charging an olefin;
b) adding a compound of formula (I):
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366
660
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where R1, R2, R3, R4, R5, R6, R7, R8 are selected from: —H, —(C1-C12)-alkyl, -Ph;
c) adding a Pt compound capable of forming a complex;
d) adding an iodine compound;
e) feeding in CO and H2;
f) heating the reaction mixture from steps a) to e), to convert the olefin to an aldehyde.
Claim 1 of ‘042-I, ‘042-II and ‘400 recites the conversion the generic olefin to the an aldehyde, but fails to recite the conversion of dicyclopentadiene to dicidal. However, the deficiency is cured by CN’978.
CN’978 teaches that tricyclodecane dicarbaldehyde (dicidal) plays a big role as an intermediate for the preparation of tricyclodecane dimethanol (dicidol), an important chemical raw material. The reference teaches that the unsaturated amorphous polyester resin composite material developed from tricyclodecane dimethanol, which is free of benzene and formaldehyde, has the characteristics of anti-yellowing and low viscosity, and has been widely used in water-based dispersions, coating compositions, lubricating oils, etc. CN’978 further teaches the use of a two-stage process and a different catalyst in the production of tricyclodecane dicarbaldehyde from dicyclopentadiene.
In accordance to MPEP 2143, the Supreme Court in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) identified a number of rationales to support a conclusion of obviousness which are consistent with the proper “functional approach” to the determination of obviousness as laid down in Graham and discussed circumstances in which a patent might be determined to be obvious. In this case, at least prong (B) simple substitution of one known element for another to obtain predictable results applies.
In this instance, using the catalyst and process steps of claims of 042-I, ‘042-II or ‘400 in place of the two-stage process and catalyst of CN’978, a skilled artisan has a reasonable expectation in arriving at the instantly claimed process, which yields nothing more than the predictable dicidol product from dicyclopentadiene. Furthermore, in view of the teachings of CN’978 about the importance of synthesizing dicidol, a skilled artisan would have been motivated to use dicyclopentadiene as an olefin starting compound of the claims of ‘042-I, ‘042-II and ‘400 with a reasonable expectation of success in obtaining dicidol.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct instantly claimed process in the conversion of dicyclopentadiene to dicidol in view of claims of ‘042-I, ‘042-II or ‘400 in combination with CN’978.
Response to Arguments
Applicant argues
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93
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119
688
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The arguments are not persuasive. The motivation and rationale to combine has been set forth above. CN’978 teaches that tricyclodecane dicarbaldehyde (dicidal) plays a big role as an intermediate for the preparation of tricyclodecane dimethanol (dicidol), an important chemical raw material and thus a skilled artisan would have been motivated to prepare tricyclodecane dicarbaldehyde (dicidal). Furthermore, since CN’978 obtains tricyclodecane dicarbaldehyde (dicidal) from dicyclopentadiene via a two-stage process, one of ordinary skilled in the art would have been motivated to use the shorter one-step process of the conflicting claims by subjecting dicyclopentadiene of CN’978 as a starting olefin with a reasonable expectation of success in arriving at the instantly claimed invention.
With respect to Applicant’s arguments of the 85% yield of dicidol obtained in claims 13-14, the examiner notes that the specification of all the above conflicting claims describe that the claimed process affords an increased yield in comparison to the method known from the prior art. Thus, a skilled artisan has a reasonable expectation that subjecting dicyclopentadiene of CN’978 to the process of the conflicting claims would result in increased yield of tricyclodecane dicarbaldehyde (dicidal), which in turn would produce a high yield of tricyclodecane dimethanol (dicidol).
Allowable Subject Matter
The subject matter of claims 1-14 is free of prior art. The closest prior art references are CN102795978A (CN’978; cited in IDS 05/03/2024 and machine translation attached herein) and Patent application publication number US2005/0101805A1 (US’805).
CN’978 teaches a method for efficiently synthesizing tricyclodecane
dicarboxaldehyde, the method comprising of first synthesizing tricyclodecane unsaturated monoaldehyde at a relatively low temperature and pressure, and then catalyzing the synthesis of tricyclodecane dicarboxaldehyde from the tricyclic unsaturated monoaldehyde at a relatively high temperature and pressure. The catalyst is a metal phosphine complex catalyst supported on a ferromagnetic oxide, and the catalyst is prepared by a coprecipitation method.
US’805 teaches a process for preparing 3(4),8(9)-bisformyltricyclo[5.2.1.02.6]decane by hydroformylating dicyclopentadiene, the process comprising two stages, in the first hydroformylation stage, the reaction is effected in a heterogeneous reaction system using an aqueous solution of transition metal compounds, containing water-soluble organic phosphorus (lll) compounds in complex-bound form, of group Vlll of the Period Table of the Elements to give 8(9)-bisformyltricyclo[5.2.1.02.6]dec-3-ene, and, in a second hydroformylation stage, the thus obtained 8(9)-bisformyltricyclo[5.2.1.02.6]dec-3-ene is converted, in homogeneous organic phase in the presence of transition metal compounds of group Vlll of the Periodic Table of the Elements to 3(4),8(9)-bisformyltricyclo[5.2.1.02.6]decane.
However, none of the above references teach or suggest the process as instantly claimed that comprises:
a) initially charging dicyclopentadiene;
b) adding a compound of formula (I):
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where R1, R2, R3, R4, R5, R6, R7, R8 are selected from: —H, —(C1-C12)-alkyl, -Ph;
c) adding a Pt compound capable of forming a complex;
d) adding an iodine compound;
e) feeding in CO and H2;
f) heating the reaction mixture from steps a) to e), to convert the dicyclopentadiene to dicidal.
As such, the instantly claimed process is deemed novel and unobvious over the closest prior art references.
Conclusion
Claims 1-14 are rejected and no claims are allowed.
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MEDHANIT W BAHTA whose telephone number is (571)270-7658. The examiner can normally be reached Monday-Friday 8am-5pm.
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/MEDHANIT W BAHTA/Primary Examiner, Art Unit 1692
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