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 .
Election/Restrictions
Restriction to one of the following inventions is required under 35 U.S.C. 121:
I. Claims 1 and 4, drawn to a diamine compound represented by a following Chemical Formula 1, a reactive monomer containing the diamine compound according to claim 1, classified in C07C217/84.
II. Claims 2 and 3, drawn to a method for preparing a diamine compound, classified in C07C201/12.
III. Claims 5 and 6, drawn to a polyimide precursor prepared by polymerizing the reactive monomer according to claim 4, classified in C08G73/105.
IV. Claim 7 and 8, drawn to a polyimide film manufactured using a solution containing the polyimide precursor according to claim 5, classified in C08G73/105.
The inventions are independent or distinct, each from the other because:
Inventions II and I are related as process of making and product made. The inventions are distinct if either or both of the following can be shown: (1) that the process as claimed can be used to make another and materially different product or (2) that the product as claimed can be made by another and materially different process (MPEP § 806.05(f)). In the instant case the product as claimed can be made by another and materially different process because the diamine compound of claim 1 can be made by a process similar to the method of claim 2, except that a Br, F, or I atom is present in place of the Cl atom in Chemical Formula 3.
Inventions I and III are directed to related products. The related inventions are distinct if: (1) the inventions as claimed are either not capable of use together or can have a materially different design, mode of operation, function, or effect; (2) the inventions do not overlap in scope, i.e., are mutually exclusive; and (3) the inventions as claimed are not obvious variants. See MPEP § 806.05(j). In the instant case, the inventions as claimed can have a materially different design, mode of operation, function, or effect because the diamine compound of claim 1 is represented by Chemical Formula 1, which is not necessarily present in the polyimide precursor of claim 5, and the polyimide precursor of claim 5 is a polyimide precursor prepared by polymerizing the reactive monomer according to claim 4 and a polymerization component including at least one acid dianhydride with each other, which is not necessarily present in the diamine compound of claim 1. Furthermore, the inventions as claimed do not encompass overlapping subject matter and there is nothing of record to show them to be obvious variants.
Inventions I and IV are directed to related products. The related inventions are distinct if: (1) the inventions as claimed are either not capable of use together or can have a materially different design, mode of operation, function, or effect; (2) the inventions do not overlap in scope, i.e., are mutually exclusive; and (3) the inventions as claimed are not obvious variants. See MPEP § 806.05(j). In the instant case, the inventions as claimed can have a materially different design, mode of operation, function, or effect because the diamine compound of claim 1 is represented by Chemical Formula 1, which is not necessarily present in the polyimide film of claim 7, and the polyimide film of claim 7 is a polyimide film manufactured using a solution containing the polyimide precursor according to claim 5, which is not necessarily present in the diamine compound of claim 1. Furthermore, the inventions as claimed do not encompass overlapping subject matter and there is nothing of record to show them to be obvious variants.
Inventions III and II are directed to an unrelated product and process. Product and process inventions are unrelated if it can be shown that the product cannot be used in, or made by, the process. See MPEP § 802.01 and § 806.06. In the instant case, the polyimide precursor of claim 5 cannot be used in, or made by, the method of claim 2 because the polyimide precursor of claim 5 is a polyimide precursor prepared by polymerizing the reactive monomer for the polyimide precursor according to claim 4 and a polymerization component including at least one acid dianhydride with each other, and the method of claim 2 is a method for preparing a diamine compound comprising reacting a compound represented by Chemical Formula 2 with a compound represented by Chemical Formula 3 under presence of a sodium hydride catalyst to synthesize a dinitro compound represented by Chemical Formula 4, and hydrogenating the dinitro compound under presence of a palladium/carbon catalyst.
Inventions IV and II are directed to an unrelated product and process. Product and process inventions are unrelated if it can be shown that the product cannot be used in, or made by, the process. See MPEP § 802.01 and § 806.06. In the instant case, the polyimide film of claim 7 cannot be used in, or made by, the method of claim 2 because the polyimide film of claim 7 is a polyimide film manufactured using a solution containing the polyimide precursor according to claim 5, and the method of claim 2 is a method for preparing a diamine compound comprising reacting a compound represented by Chemical Formula 2 with a compound represented by Chemical Formula 3 under presence of a sodium hydride catalyst to synthesize a dinitro compound represented by Chemical Formula 4, and hydrogenating the dinitro compound under presence of a palladium/carbon catalyst.
Inventions III and IV are directed to related products. The related inventions are distinct if: (1) the inventions as claimed are either not capable of use together or can have a materially different design, mode of operation, function, or effect; (2) the inventions do not overlap in scope, i.e., are mutually exclusive; and (3) the inventions as claimed are not obvious variants. See MPEP § 806.05(j). In the instant case, the inventions as claimed can have a materially different design, mode of operation, function, or effect because the polyimide precursor of claim 5 is prepared by polymerizing the reactive monomer according to claim 4 and a polymerization component including at least one acid dianhydride with each other, which is not necessarily present in the polyimide film of claim 7, and the polyimide film of claim 7 is a polyimide film manufactured using a solution containing the polyimide precursor according to claim 5, which is not necessarily present in the polyimide precursor of claim 5. Furthermore, the inventions as claimed do not encompass overlapping subject matter and there is nothing of record to show them to be obvious variants.
Restriction for examination purposes as indicated is proper because all the inventions listed in this action are independent or distinct for the reasons given above and there would be a serious search and/or examination burden if restriction were not required because one or more of the following reasons apply:
Some of the inventions have separate classification, which shows that each invention has attained recognition in the art as a separate subject for inventive effort, and also a separate field of search, and it is necessary to search for one of the inventions in a manner that is not likely to result in finding art pertinent to the other inventions, such as searching different classes/subclasses, or employing different search queries because the inventions are independent and distinct from each other as explained above.
Applicant is advised that the reply to this requirement to be complete must include (i) an election of an invention to be examined even though the requirement may be traversed (37 CFR 1.143) and (ii) identification of the claims encompassing the elected invention.
The election of an invention may be made with or without traverse. To reserve a right to petition, the election must be made with traverse. If the reply does not distinctly and specifically point out supposed errors in the restriction requirement, the election shall be treated as an election without traverse. Traversal must be presented at the time of election in order to be considered timely. Failure to timely traverse the requirement will result in the loss of right to petition under 37 CFR 1.144. If claims are added after the election, applicant must indicate which of these claims are readable upon the elected invention.
Should applicant traverse on the ground that the inventions are not patentably distinct, applicant should submit evidence or identify such evidence now of record showing the inventions to be obvious variants or clearly admit on the record that this is the case. In either instance, if the examiner finds one of the inventions unpatentable over the prior art, the evidence or admission may be used in a rejection under 35 U.S.C. 103 or pre-AIA 35 U.S.C. 103(a) of the other invention.
During a telephone conversation with Michael R. Krawzsenek on 06/26/2026 a provisional election was made without traverse to prosecute the invention of Group I, claims 1 and 4. Affirmation of this election must be made by applicant in replying to this Office action. Claims 2, 3, and 5-8 are withdrawn from further consideration by the examiner, 37 CFR 1.142(b), as being drawn to a non-elected invention.
Applicant is reminded that upon the cancelation of claims to a non-elected invention, the inventorship must be corrected in compliance with 37 CFR 1.48(a) if one or more of the currently named inventors is no longer an inventor of at least one claim remaining in the application. A request to correct inventorship under 37 CFR 1.48(a) must be accompanied by an application data sheet in accordance with 37 CFR 1.76 that identifies each inventor by his or her legal name and by the processing fee required under 37 CFR 1.17(i).
The examiner has required restriction between product or apparatus claims and process claims. Where applicant elects claims directed to the product/apparatus, and all product/apparatus claims are subsequently found allowable, withdrawn process claims that include all the limitations of the allowable product/apparatus claims should be considered for rejoinder. All claims directed to a nonelected process invention must include all the limitations of an allowable product/apparatus claim for that process invention to be rejoined.
In the event of rejoinder, the requirement for restriction between the product/apparatus claims and the rejoined process claims will be withdrawn, and the rejoined process claims will be fully examined for patentability in accordance with 37 CFR 1.104. Thus, to be allowable, the rejoined claims must meet all criteria for patentability including the requirements of 35 U.S.C. 101, 102, 103 and 112. Until all claims to the elected product/apparatus are found allowable, an otherwise proper restriction requirement between product/apparatus claims and process claims may be maintained. Withdrawn process claims that are not commensurate in scope with an allowable product/apparatus claim will not be rejoined. See MPEP § 821.04. Additionally, in order for rejoinder to occur, applicant is advised that the process claims should be amended during prosecution to require the limitations of the product/apparatus claims. Failure to do so may result in no rejoinder. Further, note that the prohibition against double patenting rejections of 35 U.S.C. 121 does not apply where the restriction requirement is withdrawn by the examiner before the patent issues. See MPEP § 804.01.
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
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.
Claims 1 and 4 are rejected under 35 U.S.C. 103 as being unpatentable over Han et al. (KR 10-2014-0096640 A, machine translation in English or untranslated patent used for citation as indicated) in view of Eswaran et al. (Eswaran et al., “Desymmetrization of meso diols using enantiopure zinc (II) dimers: Synthesis and chiroptical properties”, Applied Organometallic Chemistry, 03/25/2019, vol. 33, no. 5, p. 1-12).
Regarding claim 1, Han teaches synthesizing an adamantlyl-based diamine compound represented by the following as a monomer (translation [0005], [0090])
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(untranslated [0012], [0041, 0059], [0094]), where in the above, Ar1 and Ar2 are each independently selected from (translation [0005], [0061])
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(untranslated [0016] [0045], [0062], [0097]), wherein R1 to R4 are each independently selected from hydrogen, CF3, each of R1 to R4 may be the same or different from each other, at least one of R1 to R4 is CF3 (translation [0005], [0064]), wherein the synthesizing an adamantlyl-based diamine compound involves reacting 1,3-adamantheindiol with chloronitrobenzotrifluoride to prepare an adamantlyl-based diamine compound solution, and then purifying and drying the adamantlyl-based diamine compound solution to synthesize an adamantly-based diamine compound as a monomer (translation [0005], [0093]), wherein the chloronitrobenzotrifluoride is 5-chloro-2-nitrobenzotrifluoride (translation [0005], [0100]), which reads on a diamine compound.
Han does not teach that the diamine compound is represented by the Chemical Formula 1 as claimed. However, Eswaran teaches
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that yields
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, wherein mesohydrobenzoin and 4-nitrobenzoylchloride are reacted in the reaction (p. 8). Han and Eswaran are analogous art because both references are in the same field of endeavor of a compound derived from a diol and a chloronitrobenzene compound. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious use Eswaran’s mesohydrobenzoin to substitute for at least a fraction of Han’s 1,3-adamantheindiol in Han’s reacting 1,3-adamantheindiol with chloronitrobenzotrifluoride that is Han’s 5-chloro-2-nitrobenzotrifluoride, such that the reaction prepares a mesohydrobenzoin-based diamine compound solution, and then purify and dry the mesohydrobenzoin-based diamine compound solution to synthesize a mesohydrobenzoin-based diamine compound as a monomer, and such that the mesohydrobenzoin-based diamine compound is represented by Han’s
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except that Eswaran’s mesohydrobenzoin with the hydrogen radicals of the two hydroxyl groups substitutes for the
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. The proposed modification would read on a diamine compound represented by the Chemical Formula 1 where in the Chemical Formula 1, Ph represents a phenyl group as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying reaction properties of a Han’s chloronitrobenzotrifluoride that is 5-chloro-2-nitrobenzotrifluoride with a diol and would have been beneficial for synthesizing another diamine compound with at least two benzylene groups because Eswaran teaches
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that yields
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, wherein mesohydrobenzoin and 4-nitrobenzoylchloride are reacted in the reaction (p. 8), and because Han teaches synthesizing an adamantlyl-based diamine compound represented by the following as a monomer (translation [0005], [0090])
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(untranslated [0012], [0041, 0059], [0094]), where in the above, Ar1 and Ar2 are each independently selected from (translation [0005], [0061])
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(untranslated [0016] [0045], [0062], [0097]), wherein R1 to R4 are each independently selected from hydrogen, CF3, each of R1 to R4 may be the same or different from each other, at least one of R1 to R4 is CF3 (translation [0005], [0064]), wherein the synthesizing an adamantlyl-based diamine compound involves reacting 1,3-adamantheindiol with chloronitrobenzotrifluoride to prepare an adamantlyl-based diamine compound solution, and then purifying and drying the adamantlyl-based diamine compound solution to synthesize an adamantly-based diamine compound as a monomer (translation [0005], [0093]), wherein the chloronitrobenzotrifluoride is 5-chloro-2-nitrobenzotrifluoride (translation [0005], [0100]).
Regarding claim 4, Han teaches synthesizing a polyimide polymer by polymerizing the monomer and a dianhydride, wherein the monomer is the adamantly-based diamine compound (translation [0005], [0090, 0091]), which reads on a reactive monomer for a polyimide precursor, the reactive monomer containing the diamine compound according to claim 1 as claimed.
Claims 1 and 4 are rejected under 35 U.S.C. 103 as being unpatentable over Han et al. (KR 10-2014-0126070, machine translation in English or untranslated patent used for citation) in view of Eswaran et al. (Eswaran et al., “Desymmetrization of meso diols using enantiopure zinc (II) dimers: Synthesis and chiroptical properties”, Applied Organometallic Chemistry, 03/25/2019, vol. 33, no. 5, p. 1-12).
Regarding claim 1, Han teaches synthesizing a fluorinated diamine compound represented by the following as a monomer (translation [0006], [0084])
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(untranslated [0013], [0039], [0052]), where in the above, Ar1 and Ar2 may by the same or different from each other and may each be independently selected from (translation [0005], [0055])
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(untranslated [0016], [0043], [0056]), wherein R1 to R4 are the or different from each other and are each independently substituted or unsubstituted with a haloalkyl group, and at least one of R1 to R4 is CF3 (translation [0005], [0059]), wherein the fluorinated diamine compound can be prepared by reaction 2,2-bis(4-hydroxyphenyl)hexafluoropropane with chloronitrobenzotrifluoride in a solvent, adding potassium carbonate to prepare a fluorinated dinitro compound, and then reducing it (translation [0089], [0099]), wherein the chloronitrobenzotrifluoride is 5-chloro-2-nitrobenzotrifluoride (translation [0090]), which reads on a diamine compound.
Han does not teach that the diamine compound is represented by the Chemical Formula 1 as claimed. However, Eswaran teaches
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that yields
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, wherein mesohydrobenzoin and 4-nitrobenzoylchloride are reacted in the reaction (p. 8). Han and Eswaran are analogous art because both references are in the same field of endeavor of a compound derived from a bis hydroxy compound and a chloronitrobenzene compound. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious use Eswaran’s mesohydrobenzoin to substitute for at least a fraction of Han’s 2,2-bis(4-hydroxyphenyl)hexafluoropropane in Han’s reaction 2,2-bis(4-hydroxyphenyl)hexafluoropropane with chloronitrobenzotrifluoride that is 5-chloro-2-nitrobenzotrifluoride in a solvent, and adding potassium carbonate, such that the reaction prepares a fluorinated dinitro compound, and then reducing to synthesize a fluorinated diamine compound, and such that the fluorinated diamine compound is represented by Han’s
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except that Eswaran’s mesohydrobenzoin with the hydrogen radicals of the two hydroxyl groups substitutes for the
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. The proposed modification would read on a diamine compound represented by the Chemical Formula 1 where in the Chemical Formula 1, Ph represents a phenyl group as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying reaction properties of a Han’s chloronitrobenzotrifluoride that is 5-chloro-2-nitrobenzotrifluoride with a bis hydroxy compound and would have been beneficial for synthesizing another diamine compound with at least two benzylene groups because Eswaran teaches
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that yields
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, wherein mesohydrobenzoin and 4-nitrobenzoylchloride are reacted in the reaction (p. 8), and because Han teaches synthesizing a fluorinated diamine compound represented by the following as a monomer (translation [0006], [0084])
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(untranslated [0013], [0039], [0052]), where in the above, Ar1 and Ar2 may by the same or different from each other and may each be independently selected from (translation [0005], [0055])
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(untranslated [0016], [0043], [0056]), wherein R1 to R4 are the or different from each other and are each independently substituted or unsubstituted with a haloalkyl group, and at least one of R1 to R4 is CF3 (translation [0005], [0059]), wherein the fluorinated diamine compound can be prepared by reaction 2,2-bis(4-hydroxyphenyl)hexafluoropropane with chloronitrobenzotrifluoride in a solvent, adding potassium carbonate to prepare a fluorinated dinitro compound, and then reducing it (translation [0089], [0099]), wherein the chloronitrobenzotrifluoride is 5-chloro-2-nitrobenzotrifluoride (translation [0090]).
Regarding claim 4, Han teaches producing a polyimide film by reacting the monomer with a dianhydride to prepared a polyamide acid precursor solution, and imidizing the polyamic acid precursor solution to produce a polyimide film, wherein the monomer is the fluorinated diamine compound (translation [0006], [0083]-[0086]), which reads on a reactive monomer for a polyimide precursor, the reactive monomer containing the diamine compound according to claim 1 as claimed.
Claims 1 and 4 are rejected under 35 U.S.C. 103 as being unpatentable over Hasegawa et al. (WO 2020/158523 A1, machine translation in English or untranslated patent used for citation) in view of Eswaran et al. (Eswaran et al., “Desymmetrization of meso diols using enantiopure zinc (II) dimers: Synthesis and chiroptical properties”, Applied Organometallic Chemistry, 03/25/2019, vol. 33, no. 5, p. 1-12).
Regarding claim 1, Hasegawa teaches a method for producing a diamine compound represented by a general formula (translation [0013])
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(untranslated [0006], [0009], [0013]) as shown in the reaction equation (translation [0013])
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(untranslated [0013]), wherein the (1) is the diamine compound represented by the general formula shown above, the (5) is a diol that is 2,2’,3,3’,5,5’-hexamethylbiphenyl-4,4’-diol, and the (6) and (7) are halogenated nitrobenzenes (translation [0013]), wherein the halogenated nitrobenzenes are 5-chloro-2-nitrobenzotrifluoride (translation [0014]), which reads on a diamine compound.
Hasegawa does not teach that the diamine compound is represented by the Chemical Formula 1 as claimed. However, Eswaran teaches
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that yields
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, wherein mesohydrobenzoin and 4-nitrobenzoylchloride are reacted in the reaction (p. 8). Hasegawa and Eswaran are analogous art because both references are in the same field of endeavor of a compound derived from a diol and a chloronitrobenzene compound. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious use Eswaran’s mesohydrobenzoin to substitute for at least a fraction of Hasegawa’s
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in Hasegawa’s reaction equation
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in Hasegawa’s method for producing a diamine compound, wherein Hasegawa’s (6) and (7) are halogenated nitrobenzenes that are Hasegawa’s 5-chloro-2-nitrobenzotrifluoride, and such that Eswaran’s mesohydrobenzoin with the hydrogen radicals of the two hydroxyl groups substitutes for the
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in Hasegawa’s
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. The proposed modification would read on a diamine compound represented by the Chemical Formula 1 where in the Chemical Formula 1, Ph represents a phenyl group as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying reaction properties of Hasegawa’s (6) and (7) that are halogenated nitrobenzenes that are Hasegawa’s 5-chloro-2-nitrobenzotrifluoride with a diol and would have been beneficial for producing another diamine compound with at least four benzylene groups because Eswaran teaches
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that yields
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, wherein mesohydrobenzoin and 4-nitrobenzoylchloride are reacted in the reaction (p. 8), and because Hasegawa teaches a method for producing a diamine compound represented by a general formula (translation [0013])
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(untranslated [0006], [0009], [0013]) as shown in the reaction equation (translation [0013])
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(untranslated [0013]), wherein the (1) is the diamine compound represented by the general formula shown above, the (5) is a diol that is 2,2’,3,3’,5,5’-hexamethylbiphenyl-4,4’-diol, and the (6) and (7) are halogenated nitrobenzenes (translation [0013]), wherein the halogenated nitrobenzenes are 5-chloro-2-nitrobenzotrifluoride (translation [0014]).
Regarding claim 4, Hasegawa teaches a polyimide produced using the diamine compound (translation [0013]) and a polyimide synthesized using the diamine compound by reacting the diamine compound with an acid dianhydride to produce the polyimide (translation [0015]), which reads on a reactive monomer for a polyimide precursor, the reactive monomer containing the diamine compound according to claim 1 as claimed.
Correspondence
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DAVID KARST whose telephone number is (571)270-7732. The examiner can normally be reached Monday-Friday 8:00 AM-5:00 PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Mark Eashoo can be reached at 571-272-1197. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/DAVID T KARST/ Primary Examiner, Art Unit 1767
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