DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA . Per amendment dated 6/25/26 claims 1-17 are currently pending in the application.
It is noted that claims 16 and 17 are newly added claims in the amendment, with claim 16 further limiting the scope of the polymer of withdrawn claim 7. Thus, claims 1-6 and 17 read on the elected invention. Claims 7-16 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.
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.
Claims 1-6, 17 are rejected under 35 U.S.C. 103 as being unpatentable over Critchley et al. (GB 1216505 A (GB’505), of record).
Regarding claims 1-3, Critchley teaches a process of reacting a diamine with an aromatic tetracarboxylic acid dianhydride or derivative thereof (reads on (AC), of following formulae:
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and
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,
wherein X in the diamine may be a divalent group, such as a perfluoroalkylene group -(CF2)n- wherein n is an integer ranging from 1 to 9, and A is represented by one of the following formulae:
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wherein Y is a -CO-, -O- or a perfluoroalkylene group -(CF2)n- with n being an integer ranging from 1 to 9 (page 1, line 44-page 2, line 97, ref claims 12 and 13). Thus, the disclosed diamines include those with an even number of –(CF2)- groups (i.e., 2, 4 and 6 groups) of the claimed invention. Additionally, noting that the positions of the amine groups on the aromatic rings. relative to the –(CF2)- linkage, are open ended in the diamine formula above, disclosed diamine formula encompasses diamine components (II)-(IV) of the claimed invention.
Disclosed anhydrides and derivatives thereof include, for e.g., dianhydride of pryomellitic acid (reads on PMDA), of diphenylether 3,3’,4,4’-tetracarboxylic acid (reads on OPDA), and diacids/diesters thereof (page 2, lines 81-88, read on claimed (AC)).
Critchley teaches a process wherein the reaction may be carried out in a melt, or in a polar aprotic solvent and the initial product is a polyamic acid (page 2, lines 98-106, ref. claims 14, 15).
Critchley is silent on a polyamic acid obtained by reacting a polyamine of formula (II)-(IV) in a single embodiment as claimed.
At the outset, it is noted that in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976). See MPEP § 2144.05.
Given the teaching on suitable components for reacting in a polar aprotic solvent to form a polyamic acid as an initial product, and noting that the generic diamine formula is open ended to even number of -(CF2)- groups and to the position of the amino group on the aromatic ring relative to the -(CF2)- group, it would have been obvious to one of ordinary skill in the art, as of the effective filing date of the claimed invention, to prepare a polyamic acid by reacting any polyamine and an aromatic dianhydride dianhydride compound, including those within the scope of the claimed invention.
Regarding claim 4, Critchley teaches dianhydride of pyromellitic acid (reads on PMDA) and diphenylether 3,3’,4,4’-tetracarboxylic acid (reads on OPDA), and diacid/diesters thereof (page 2, lines 81-88, read on claimed (AC)). Although the scope of alkyl groups in the diesters is not disclosed, the limitation in claim 4 does not necessarily limit the scope of claim 1 given that anhydrides and compounds of formula (V) are recited in the alternative.
Regarding claims 5 and 6, based on the diamine formula above encompassing 1-9 -(CF2)- groups, i.e., equivalence of the species, it would have been obvious to one of ordinary skill in the art at the time of the invention to react a combination of diamines, for instance, a blend of diamine having any of 2, 4 or 6 -(CF2)- groups (corresponding to claimed formulae (IV), (II) and (III), respectively, read on (D)) with any diamine having an odd number of -(CF2)- groups (read on (D1)), for e.g., in a 1:1 molar ratio, based on their art recognized equivalence, with an aromatic tetracarboxylic acid dianhydride to form a polyamic acid, including those of the claimed invention.
Regarding the (AC) component recited in claim 6, Critchley teaches dianhydride of the following formula:
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, and A may be
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wherein Y is open to being linked to any carbon on the aryl rings, and may be an oxygen atom (i.e., may be 4,4’-oxydiphthalic anhydride (ODPA) (page 1, line 49-page 2, line 9).
In this case, it would have been obvious to one of ordinary skill in the art at the time of the invention to combine a diamine with an even number of -(CF2)- groups and those having an odd number of -(CF2)- groups, as the two are considered to be equivalents known for the same purpose. “It is prima facie obvious to combine two compositions each of which is taught by the prior art to be useful for the same purpose, in order to form a third composition to be used for the very same purpose.... [T]he idea of combining them flows logically from their having been individually taught in the prior art.” In re Kerkhoven, 626 F.2d 846, 850, 205 USPQ 1069, 1072 (CCPA 1980). MPEP 2144.06. Additionally, it would have would have been prima facie obvious, using no more than ordinary creativity, logic, judgment, and common sense, to combine diamine with and odd number of carbon atoms in equal amounts (i.e. in a 1:1 molar ratio) based on the fact that both are disclosed in parallel as being equally suitable for use in this capacity. This 1:1 ratio falls within the claimed ratio.
Regarding claim 17, for reasons stated above, one of ordinary skill in the art would have found it obvious to prepare a polyamic acid of instant claim 1 by polymerizing the claimed components by substantially a similar process as disclosed in the instant specification. It is further noted that the original specification does not identify any feature that results in the claimed effect or physical property outside of the presence of the claimed components in claimed amounts. Therefore, it would have been obvious to a skilled artisan to reasonably expect Critchley’s polyamic acids of overlapping scope to have the claimed feature(s) on the basis that materials and their properties are inseparable, absent evidence to the contrary. As a practical matter, the Patent Office is not equipped to manufacture products by the myriad of processes put before it and then obtain prior art products and make physical comparisons.
Claims 1-6, 17 are rejected under 35 U.S.C. 103 as being unpatentable over Flattery et al. (WO 95/04305 A1, of record).
Regarding claims 1-3, Flattery teaches a photosensitive composition comprising a fluorinated polyamic acid of the following formula, formed from either an aromatic tetracarboxylic dianhydride and/or an aromatic diamine that is fluorinated (Ab., page 7):
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wherein, A may be, for e.g., a radical shown below:
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and B may be, for e.g., a divalent radical of a diamine shown below:
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wherein R1 may be -(C4-7F8-14)-, m may be 0, and the position of the amine group of the aryl rings, relative to R1 is open ended, i.e., can be at the para position (Ab., pages 4-5, 9, ref. claims).
Flattery teaches that either the diamine or the dianhydride may be fluorinated (page 7, lines 22-24), and disclosed genus of anhydrides include pyromellitic dianhydride, 3,3’,4,4’-biphenyl tetracarboxylic acid dianhydride, 2,2-bis (3,4-dicarboxyic hexafluoropropane dianhydride etc. (read on (AC) (page 12, lines 1-12).
Disclosed genus of suitable diamines include 1,3-bis(4-aminophenyl) hexafluoropropane, 1,5-bis(4-aminophenyl)decafluoropentane, 1,7-bis(4-aminophenyl)tetradecafluoroheptane, and 2,2-bis(4-aminophenyl)hexafluoropropane. That is, Flattery teaches equivalence of such monomers.
Disclosed polyamic acids in the Examples are prepared by reacting an anhydride and a diamine, preferably at a molar ratio of 0.98 to 1.0 of diamine to dianhydride (page 13, lines 1-2, page 22, lines 1-11).
Flattery is silent on a polyamic acid formed from a diamine as claimed.
As stated in paragraph 7 above, in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists.
Given the teaching in Flattery on suitable dianhydrides and diamines of above formula having -(C4-7F8-14)-, wherein m may be 0 and the amine group of the aryl rings may be at any position relative to R1 linkage, and the teaching on suitable species of the diamine, it would have been obvious to one of ordinary skill in the art, as of the effective filing date of the claimed invention, to prepare a polyamic acid from a diamine and a dianhydride as in claimed invention.
In the alternative, the claimed compounds of formulae (II) to (IV) are homologs of the disclosed species - 1,3-bis(4-aminophenyl)hexafluoropropane, 1,5-bis(4-aminophenyl)decafluoropentane, 1,7-bis(4-aminophenyl)tetradecafluoroheptane, i.e., compounds differing regularly by the successive addition of the same chemical groups, in the present instance, a -CF2- group. Homologs “are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties”. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). Additionally, Flattery describes similarities in utility of prior art compounds and claimed compounds, i.e., as suitable amino compounds for preparing polyamic acids. A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. "An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties." In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979).
Thus, given the teaching in Flattery on suitable diamines for preparing the polyamic acids, it would have been obvious to one of ordinary skill in the art, as of the effective filing date of the claimed invention, to modify Flattery to select a homolog of the disclosed diamine species, such as compounds of formulae (II), (III) or (IV) as such compounds are expected to possess similar properties and have similar utility relative to the claimed compounds.
Regarding claim 4, noting that Flattery teaches aromatic tetracarboxylic dianhydrides, the limitation in claim 4 does not necessarily limit the scope of claim 1 given that anhydrides and compounds of formula (V) are recited in the alternative.
Regarding claims 5 and 6, the polyamic acid of Example 9 is formed from 3,3’,4,4’-biphenyl tetracarboxylic acid dianhydride (BPDA,100 mole%)/p-phenylenediamine (reads on D1) (PPD, 70 mole%)/2,2-bis(4-aminophenyl)hexafluoropropane (6FDAM, 30 mol%). It would have been obvious to a skilled artisan to substitute 2,2-bis(4-aminophenyl)hexafluoropropane with an equivalent monomer, e.g., a diamine of the disclosed formula having an even number of -(CF2)- groups and an amino group at the para position to the -(CF2)- group, or alternatively, relying on a homolog of the disclosed diamine species, with a reasonable expectation of success, absent evidence to the contrary.
Regarding claim 17, for reasons stated above, one of ordinary skill in the art would have found it obvious to prepare the polymer of instant claim 1 by polymerizing the claimed compounds, by substantially a similar process as disclosed in the instant specification, and to reasonably expect the polyamic acids, modified as suggested above to include homologs, to have the claimed feature(s) on the basis that materials and their properties are inseparable, absent evidence to the contrary.
Response to Arguments
In the view of the amendment dated 6/25/26, the 103 rejections based on Critchley (GB ‘505) and Flattery are withdrawn and modified rejections are presented herein above. The Critchley (J. Polym. Sci.) and Mueller rejections of record are withdrawn in view of the amendment but the art would be applicable under 103 though not relied upon in the office action as the rejections would be of cumulative nature. Applicant’s arguments dated 6/25/26 have been duly considered.
As an initial matter, it is noted that the preamble in claim 1 is amended to recite “A polyamic acid polymer in which part or all of the amic acid groups are in the form of an ester”. While the recitation “polyamic acid polymer” implies amic acid groups as being necessarily present, the recitation “all of the amic groups are in the form of an ester” is conflicting. Although Examiner is not levying a new grounds of rejection in order to maintain compact prosecution, Applicant is advised to alerted to the same for future reference.
In the context of Mueller reference (now withdrawn), Applicant presents that with a 1,4 arrangement of the -NH₂ to the CF₂ groups across the aromatic rings, the polyimide polymers and precursors thereof having improved dielectric performances while possessing appropriate solubility and low water absorption, have mechanical properties that can be conveniently modulated to suit the needs of the microelectronic industry. Applicant refers to the comparative examples as failing to demonstrate adequate dielectric properties shown by inventive polymers.
Regarding Critchley ‘505 reference, and referring back to arguments made against Mueller, Applicant argues that polyamic polymers that convert to polyamides and formed from claimed diamines of formula (II)-(IV), having a para substituted arrangement and 2, 4 or 6 -(CF2)-groups, provide for superior properties, when compared to diamines formed from diamines having odd number of -(CF2)- groups that do not provide for adequate properties in microelectronic applications, that none of the exemplified diamines in GB ‘505, which exclusively have odd number of fluoroalkyls, suggest or motivate a person of ordinary skill towards including only even numbered fluoroalkyl groups as claimed. Referring to GB 505, Applicant further argues on numerous possible applications of the disclosed materials and that there is no teaching or suggestion that the instantly claimed components, particularly the diamines with even number perfluoralkylene groups, could convert to polyimide polymers that may possess properties suitable for microelectronics as claimed.
Regarding the Flattery reference, Applicant argues that Flattery also teaches hexafluoropropane diamines, that comparative examples CA1-CA2 demonstrate that Flattery's hexafluoropropane diamine is not suitable in forming polyimide films with adequate properties and therefore, a person of ordinary skill in the art would not have had a reasonable expectation of success or motivation to modify Flattery's diamine to those of the instant claims.
In response, as stated in the rejections herein above, the disclosed generic formula of the diamine in both, Critchley and Flattery references, encompass diamines having even number of -(CF2)- groups, and the position of amino group, relative to the -(CF2)- group in both references are open ended and thus, can be at the para position as in the claimed invention. While Flattery (and not Critchley) teaches a variety of applications, nevertheless, it includes electronic circuit substrates. Even so, the claims of the elected invention are drawn to a polyamic acid polymer, and given the teaching on suitable aromatic dianhydrides and diamines of overlapping scope for forming polyamic acids, Examiner maintains that the claimed polyamic acids are obviated by Critchley and Flattery references.
Although examples in Critchley and Flattery teach homologs and/or isomers of the claimed diamine species, a teaching contained in a reference’s broader disclosure may be relied upon despite not appearing in the reference’s examples. Disclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or nonpreferred embodiments. In re Susi, 440 F.2d 442, 169 USPQ 423 (CCPA 1971). A reference may be relied upon for all that it would have reasonably suggested to one having ordinary skill the art, including nonpreferred embodiments. Merck & Co. v. Biocraft Laboratories, 874 F.2d 804, 10 USPQ2d 1843 (Fed. Cir.), cert. denied, 493 U.S. 975 (1989). See MPEP 2123.
Furthermore, upon considering the data in page 26 (Table 4), it is noted that all but one inventive polyimide (F2), are derived from DA6 as the sole diamine or as one of the plurality of diamine components. Additionally, the Dk values for the Inv. polyimides (F1-F15) (derived from polyamic acid), range from 2.4 to 3.7, while those of Comp. polymers (CF1-CF4) range from 2.3 to 3.5, i.e., are of overlapping scope. It is further noted that the Dk values of Inv. polyimides (F1-F15) range from 0.0015 to 0.0044, lower than those of Comp. polyimides CF1, CF2 and CF4, ranging from 0.0062 to 0.0068.
Furthermore, in comparing the Dk and Df values of Comp. polyimides CF3 and CF4, it is noted that both rely on PDA, i.e., a diamine outside of the scope of the inventive diamine, and yet, a polyimide formed from of OPDA with PDA has a Dk of 3.5 and Df of 0.0037 (CF3), while a polyimide formed from of BPDA with PDA has a Dk of 3.5, but a significantly higher Df, of 0.0068 (CF4). Noting that the Dk values of CF3 and CF4 are the same as that of Inv. polyimide F15, based on the difference in Df values of CF3 and CF4, Examiner infers that it is not only the choice of the diamine component as argued by the applicant, but also the choice of the dianhydride component that contributes to dielectric values of a polyimide. Even so, the data on record on the asserted superior performance would be limited to specific polyimides derived from specific AC components and diamine components, whereas claim 1 is of a much broader scope and not reasonably commensurate in scope with the claim language.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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 Satya Sastri at (571) 272 1112. The examiner can be reached Monday-Friday, 9AM-5.30PM (EST). If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Mr. Robert Jones can be reached at (571)-270-7733. The fax phone number for the organization where this application or proceeding is assigned is (571) 273 8300.
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/Satya B Sastri/
Primary Examiner, Art Unit 1762
Prosecution Insights