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 .
Claims 1, 3-10, 16-18 and 20-25 are pending as amended on 6/12/2026.
Claims 3, 4, 7-10 and 20-25 stand withdrawn from consideration.
Note that the claim listing filed on 6/12/2026 does not present the status of every claim as required by 37 CFR 1.121 (c). Claims 14 and 15 should be included in the claim listing with the status of each claim (canceled) indicated after its claim number.
The new/modified grounds of rejection set forth herein were necessitated by Applicant’s amendment. Therefore, this action is properly made final. Any rejections and/or objections made in the previous Office action and not repeated below are hereby withdrawn. The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office Action.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1, 5, 6 and 16-18 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c).
In the present instance, claim 1 recites that the conjugated diene structure includes at least one of DE1 and DE2 (see p “3” of the claims). The claim also recites that the conjugated structure includes at least one of structures represented by formula DE5, which is the narrower statement of the range/limitation (because DE5 is a narrower embodiment of DE1. Claim 1 (and each claim which depends from claim 1) is considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
For examination purposes, the claims have been interpreted as requiring the conjugated diene structure to include at least one structure represented by Formula DE5. Applicant may wish to consider amending claim 1 to delete the broader recitation requiring structure of DE1 or DE2.
Additionally: claims 5 and 6 depend from claim 1 and further limit the positioning of “the dienophile structures” in the polymer. However, claim 1 is now limited to a resin formed by reaction between a polymer having diene structures and a compound having dienophile groups. Claim 1 does not recite a polymer having a dienophile structure. Therefore, references to “the dienophile structures” in a polymer recited in claims 5 and 6 lack antecedent basis, rendering the scope of the claims unclear.
Claim Rejections - 35 USC § 103
Claim(s) 1, 5, 6, 16 and 17 is/are rejected under 35 U.S.C. 103 as being unpatentable over Flanagan et al (US 2020/0032060) in view of Hyodo et al (US 2012/0232240).
This is a rejection of resin formed by a Diels-Alder reaction between:
an aromatic polycarbonate as conjugated diene which is formed from BisZ and BIPANT, as in instant PC-5, and
a compound having two or more maleimide (i.e., dienophile) groups,
wherein the reaction of maleimide group(s) in the compound with anthracene group(s) in the polycarbonate forms bonds between polymer chains.
This embodiment is a resin encompassed by instant claims 1, 5, 6, 16, 17 and 19.
Flanagan teaches polymer adducts endowed with improved or additional properties with respect to those of the starting polymers [0002]. Flanagan further teaches that the formation of adducts represents a convenient way of obtaining high molecular weight polymeric structures from polymers of lower molecular weight, without rearrangement and randomization of polymer repeat units [0058]. Additionally, the adduct formation is reversible, and can be exploited for recycling, and to provide coatings that can be easily repaired by self-healing [0057].
For the formation of polymer adducts, Flanagan discloses a blend comprising an aromatic polymer (P1) which can be a polycarbonate (PC), and which comprises at least one moiety M1, which has the following structure:
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[0050-52]. The at least one moiety M1 can be at one or both ends of the polymer chain, and/or can be a pendant group, and/or can be included in the polymer chain [0060-65]. Flanagan teaches that a polycarbonate can be formed by the addition of anthracene moieties having two or more functional groups capable of participating in the polymerization reaction, such that the anthracene moiety becomes incorporated into the polymer chain [0079]. A polycarbonate formed from polymerization of a polyfunctional anthracene moiety to provide anthracene moieties incorporated in the polymer chain, as disclosed by Flanagan, is an aromatic polycarbonate having two or more conjugated diene structures (anthracene structures) in the main chain of the polymer chain. Additionally, the three possible M1 locations within a polymer chain disclosed by Flanagan in [0062-65] are separated by “and/or,” which means that M1 can be located at all three of the disclosed locations, or, located at only one of the disclosed locations. Therefore, one would have clearly envisaged embodiments wherein the moiety M1 is included in a polymer chain as taught in [0065], but not at both ends of the polymer chain as taught in [0063], meeting the recitations of instant claim 5.
Flanagan teaches four preferred aromatic diols for forming a polycarbonate, including 1,1-bis-(4-hydroxyphenyl)cyclohexane [0223] (i.e., “BisZ”). Flanagan further teaches that the amount of (M1)/anthracene units in the polymer can range from 0.1 to 100 mol%, e.g., 0.5 to 25 mol% [0067]. While Flanagan polycarbonate formed from BisZ and further discloses addition of anthracene moieties having two or more functional groups capable of participating in the polymerization reaction [0079], Flanagan fails to teach a polycarbonate having units derived from BisZ and from anthracene monomers in the main chain having a structure according to instant DE5.
Hyodo teaches that bisphenol compounds having at least two aromatic rings have been used for producing various types of novel polymers, including polycarbonate resins, by means of reactivity of a hydroxyl group bound to the aromatic ring in the molecule. Hyodo teaches that resins derived from bisphenol compounds are employed in a variety of intended usages, and have a versatility that allows for a large variety of developments of applications [0008, 0060]. Hyodo teaches an anthracene derivative having characteristics peculiar to anthracene, and reaction diversity that results from the bisphenol structure [0017]. Hyodo discloses an anthracene derivative having the following formula I [0018]:
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wherein X and Y are preferred to be hydroxyphenyl groups [0021] (Hyodo exemplifies 9-(4-hydroxybenzyl)-10-(4-hydroxyphenyl)anthracene, which has a structure wherein X and Y are 4-hydroxyphenylene groups; Example 1 [0110]). The functional groups enable use as a basic material for synthesizing various resins [0022], and introduction into the polymer main chain is permitted [0050]. Hyodo also teaches that placement of the phenol skeletons at positions 9 and 10 (short axis) of the anthracene skeleton achieves high carbon density or gives high crystallinity when introduced into the polymer chain [0050].
Considering Hyodo’s disclosure, when introducing anthracene units in the main chain of a polycarbonate resin, the person having ordinary skill in the art would have been motivated to utilize an anthracene compound such as 9-(4-hydroxybenzyl)-10-(4-hydroxyphenyl)anthracene in order to effectively introduce an anthracene structure into the main chain via the versatile reactivity of bisphenol groups. It would have been obvious to the person having ordinary skill in the art, therefore, to have formed a polycarbonate polymer P1 by polymerization of BisZ, and by adding anthracene monomers having functionality capable of participating in the polymerization reaction, as disclosed by Flanagan, by utilizing Hyodo’s 9-(4-hydroxybenzyl)-10-(4-hydroxyphenyl)anthracene as the anthracene monomer, thereby arriving at a polycarbonate P1 having a structure which includes anthracene groups according to DE5 (wherein X1 is -O-) and BisZ units according to instant formula UN1 (wherein in instant formula UN11, X3 is cyclohexylene, m3 is 1 and R3 is H (and which has a structure according to instant species PC-5).
Flanagan teaches that the blend can comprise a polymer P2 having maleimide end groups [0080]. Alternatively, Flanagan teaches including bismaleimides as thermal adduct formers [0232]. Flanagan exemplifies both types of embodiments: See Example 7, wherein chain extension of a polymer P1 is achieved by reaction (heating) of anthracene in P1 with maleimide-terminated polymer P2 [0297] (note that Flanagan characterizes the adduct formation as being “Diels-Alder” [0299]). See also Example 8, wherein chain extension of a polymer P1 is achieved by reaction (heating) of anthracene in P1 with 4,4’-bismaleimido-diphenylmethane as a thermal adduct former [0300].
Considering Flanagan’s disclosure regarding the advantages associated with the disclosed adduct formation, the person having ordinary skill in the art would have been motivated to select any appropriate structure for the maleimide-containing adduct forming component (i.e., a polymer P2 or a thermal adduct former such as 4,4’-bismaleimido-diphenylmethane), in order to provide a final product (article, coating, etc.) having appropriate properties according to the requirements of a given application. It would have been obvious to the person having ordinary skill in the art, therefore, to have formed an adduct by reaction of anthracene groups in the polycarbonate P1 with maleimide, as disclosed by Flanagan, by selecting any appropriate maleimide structure disclosed by Flanagan in [0232], including e.g., 4,4’-bismaleimido-diphenylmethane (as exemplified in [0300]), which is a difunctional dienophile compound having a structure according to DP1 and DP2 recited in claims 16 and 17 (wherein X2 is a linking group containing covalently bonded carbon atoms). The fact that Flanagan discloses several types of polymer P1 and several types of maleimides to form an adduct with P1 does not render any particular combination of P1 or maleimide less obvious. A reference is available for all that it teaches to a person of ordinary skill in the art. Merck & Co., Inc. v. Biocraft Laboratories, Inc. 874 F.2d 804, 807 (Fed. Cir. 1989).
Claim(s) 1, 5, 6 and 16-18 is/are rejected under 35 U.S.C. 103 as being unpatentable over Flanagan et al (US 2020/0032060) in view of Hyodo et al (US 2012/0232240) and Herr et al (US 2012/0082840).
This is a rejection of the elected species, i.e., a resin formed by a Diels-Alder reaction between:
an aromatic polycarbonate as conjugated diene which is formed from BisZ and BIPANT, as in instant PC-5, and
a compound having two or more maleimide (i.e., dienophile) groups according to instant MI-BisA.
The elected species is encompassed by instant claims 1, 5, 6 and 16-18.
The rejection over Flanagan in view of Hyodo above is incorporated here by reference.
Modified Flanagan suggests a resin formed by reaction of aromatic polycarbonate according to instant PC-5 with a bismaleimide, as set forth above. As discussed previously, Flanagan teaches including bismaleimides as thermal adduct formers [0232], and exemplifies chain extension of a polymer P1 by reaction (heating) of anthracene in P1 with 4,4’-bismaleimido-diphenylmethane as a thermal adduct former [0300]. Flanagan further names other bismaleimides in [0232] (1,2-, 1,3-, and 1,4-phenylene dimaleimides). However, Flanagan fails to name a bismaleimide which has a structure according to instant MI-BisA.
Herr discloses a non-linear polymer network formed from a multifunctional diene monomer or prepolymer and a multifunctional dienophile monomer or prepolymer [0007]. Herr discloses that the multifunctional diene has a general structure L-(X)P where “L” can be polycarbonate, X is a diene (including anthracene) and P is greater than zero. The multifunctional dienophile has a structure L-(Y)Q wherein Y is a dienophile group and Q is greater than zero [0008, 0018]. Herr discloses aromatic bismaleimide resins as suitable dienophiles, which have structures according to the general formula L-(Y)Q wherein Y is maleimide and Q is 2 [0025].
Herr teaches that suitable aromatic bismaleimide resins are particularly those having a structure
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wherein Q is aromatic [0025]. Herr teaches several “Q” structures on p 5. The second and third “Q” structures shown in [0025] correspond to the same bismaleimides taught by Flanagan (i.e., phenylene dimaleimides and bismaleimido-diphenylmethane). Herr further teaches a bismaleimide wherein Q is:
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In view of the limited possible points of attachment (three: para, meta, ortho), one having ordinary skill in the art would have immediately envisaged the structure taught by Herr with any of the three possible attachments, including para- as in instant MI-BisA.
Considering that both Flanagan and Herr disclose reversible adducts formed by reaction of polycarbonates including anthracene moieties as dienes and bismaleimides as dienophiles, and further given that the suitable bismaleimides named by Flanagan and Herr include several of the same compounds, one having ordinary skill in the art could have predictably substituted a bismaleimide adduct former named by Flanagan for another bismaleimide adduct former named by Herr, with a reasonable expectation that any of the named bismaleimide adduct formers would effectively react with anthracene moieties in Flanagan’s polycarbonate in order to increase the molecular weight thereof. It would have been obvious to the person having ordinary skill in the art, therefore, to have reacted an anthracene-containing polycarbonate P1 with a bismaleimide adduct former, as suggested by Flanagan, by substituting the phenylene- or diphenylmethane- bismaleimide compound named by Flanagan for another bismaleimide adduct former known in the art, including a bismaleimide adduct former having a structure according to instant MI-BisA, as taught by Herr. Case law has established that it is prima facie obvious to substitute one known element for another to obtain predictable results. KSR Int'l Co. v. Teleflex, Inc., 550 U.S. 398 (2007). MPEP 2143, rationale (B).
Response to Arguments
Applicant's arguments filed 6/12/2026 have been fully considered.
Applicant argues (p 12) that Flanagan does not teach the recited DE5 structure. This argument fails to establish nonobviousness for at least the reason that secondary reference Hyodo was relied on for a teaching of this structure.
Applicant argues (p 12) that Flanagan and Hyodo do not teach a main chain of aromatic polycarbonate or polyarylate. However, the rejection of record cites specific portions of Flanagan to establish that Flanagan teaches a main chain of an aromatic polycarbonate. Applicant has not explained why the cited teachings in Flanagan do not satisfy the instant recitation of a main chain of aromatic polycarbonate.
Applicant argues (p 12) that Herr discloses a multifunctional diene monomer that contains a furan ring, and therefore Herr would teach away from the instant claims. However, Herr was relied on as a secondary reference to establish that, when forming a resin by reaction of bismaleimide with an aromatic PC containing a conjugated diene (as suggested by modified Flanagan), it would have been obvious to have substituted one known bismaleimide for another (see paragraphs 62-66 of the previous action). Applicant's argument fails to establish nonobviousness for at least the reason that it does not appear to consider that Herr's disclosed list of suitable multifunctional dienes "X" includes anthracene in addition to furan.
Applicant argues (pp 12-13) that the instant examples and comparative examples (table 1) show unexpected effects (solvent/abrasion resistance, reduced degradation) associated with the claimed resin. However, none of the comparative examples in Table 1 are formed from a composition which includes any dienophile crosslinker. For at least the reason that Applicant has not explained how the instant comparative examples could be representative of the closest prior art (primary reference Flanagan teaches including a polymer P2 having maleimide end groups or a bismaleimide thermal adduct former), Applicant's data fails to overcome the rejections of record.
Additionally, Applicant argues (p 13) that the differences in properties between the examples in Table 1 are unexpected. Applicant has not explained or established what differences in properties would have been expected based on the differences between a crosslinked and uncrosslinked structure, nor how the data shown in table 1 is unexpectedly different from a result which would have been expected. Therefore, Applicant has not adequately established that the properties in table 1 show unexpected results.
Additionally, Applicant is advised that evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support. See MPEP 716.02(d). Therefore, if Applicant wishes to overcome the present rejection by showing unexpected results, Applicant must provide sufficient evidence to show that unexpected results would be obtained for all species encompassed by the present claims.
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 RACHEL KAHN whose telephone number is (571)270-7346. The examiner can normally be reached Monday to Friday, 8-5.
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/RACHEL KAHN/ Primary Examiner, Art Unit 1766
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