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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 5/18/2026 has been entered.
Status of Claims
The examiner acknowledges the amendments to claims 1, and 7-9. Claims 1-4 and 7-15 are pending.
Claim Objections
Claim1 is objected to because of the following informalities: the lines that begin with “each occurrence of” R5a and R5b, there appears to be a missing comma between (C1-6-hydrocarbyl) and (C1-6-hydrocarbyl)aminomethylene group. Appropriate correction is required.
Claim Rejections - 35 USC § 112
The applicant has amended claims 1 and 7-9. As a result, the previous 112 rejections are withdrawn.
Claim 13 is 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.
Claim 13 refers to "the process of claim 1", however claim 1 is directed towards a capped poly(arylene ether) copolymer with no reference to a process. As a result, there is insufficient antecedent basis for this limitation in the claim. The applicant is required to amend the claim language. For the purposes of examination, the language of claim 1 will be interpreted to mean “the process of claim 10”.
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 1-4 and 7-15 are rejected under 35 U.S.C. 103 as being unpatentable over Carrillo (US 20090062478) in view of Tarkin-Tas (WO 2018194797, Foreign Reference #3 from IDS dated 11/10/2022 herein using US version US 20200172729, US Patent Publication #1 from IDS dated 8/22/2024).
Regarding Claims 1, 3-4, and 7,
Carrillo teaches a capped poly(arylene ether) (Paragraph 3) that is comprised of monophenol monomers of the following structure:
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where each Z1 can independently be a variety of groups including halogens, and substituted C1-C12 hydrocarbons, where hydrocarbon includes both aliphatic and aromatic groups (Paragraph 8) (corresponds to Q1a, R5a, Q1b, and R5b of the structures of the instant claims) and Z2 can be the same groups with the addition of hydrogen (Paragraph 8) (corresponds to Q2 in the structures of the instant claims), meeting the requirements of the instant claims. Additionally, the poly(arylene ether) can also contain structures with two phenolic groups and is of the following structure:
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where R1-R4 can each be hydrogen, halogen, or C1-C12 hydrocarbons, amongst other options (Paragraph 10), meeting the requirement of the instant claims. The Y group can be the following structures (corresponding to Y1 of the instant claims):
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and Z can be 0 or 1, meeting the requirement of the instant claims. Carrillo also teaches that when using the bifunctional phenol described above, that the number of monomer units on each side may independently be from 0 to 30, provided that the sum of the monomer units is equal to at least 2 (Paragraph 10). Carrillo teaches that the polymer is capped using a variety of capping agents, including halohydrocarbons or acryloyl or methacryloyl chloride (Paragraph 18), meeting the requirements of the instant claims.
Finally, while Carrillo does teach the use of monomers that contain alkyl and aryl substituents, Carrillo does not explicitly call for the use of aryl substituted monomers. However, Tarkin-Tas teaches a poly(phenylene ether) copolymer that includes 2,6-dimethylphenol and a dihydric phenol along with 2-methyl-6-phenylphenol (Abstract) and further teaches that the incorporation of the aryl groups increases the solubility of the resulting polymers as well as lowering the solution viscosity (Paragraph 8).
One of ordinary skill in the art would be motivated to incorporate a monomer such as 2-methyl-6-phenylphenol because Tarkin-Tas notes that by increasing the solubility of the copolymer reduces the amount of solvent required to work with the copolymer as well as reducing flammability and lowering the temperatures required to promote dissolution (Paragraph 2). Further, by reducing viscosity, the copolymer could be more easily dispensed during the formation of a cured article. Additionally, as Tarkin-Tas and Carrillo both disclose poly(arylene ether) copolymers of similar composition and for use in curable compositions for use in electronics (Carrillo Paragraph 1, Tarkin-Tas Paragraph 1), it would have been obvious to have incorporated the 2-alkyl-6-arylphenol monomer taught by Tarkin-Tas into the composition of Carrillo to achieve the predictable result of a poly(arylene ether) copolymer with improved solubility and viscosity characteristics with a reasonable expectation of success.
Regarding Claim 2,
Carrillo teaches the use of bifunctional poly(arylene ethers), which are stated specifically to have two phenolic hydroxy groups (Paragraph 10) and that the conditions should result in complete capping (Paragraph 18), meeting the requirement of the instant claim.
Regarding Claims 8-9,
Carrillo teaches the use of tetramethylbisphenol A as the bifunctional phenol (Paragraph 46) that is then further reacted with 2,6-dimethylphenol and finally capped with methacrylic anhydride (Paragraph 46), which combined with repeat unit restrictions described above in regard to claims 1 and 5-6 meets the requirements of the instant claims.
Regarding Claims 10, and 13,
Carrillo teaches the monophenol of the following structure
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can have Z2 groups that can be hydrogen (Paragraph 8) as well as Z1 groups that can independently be C1-C12 hydrocarbyl groups that can be aliphatic or aromatic (Paragraph 8), meeting the requirements of the instant claim. Carrillo additionally teaches that the poly(arylene ether) can be synthesized from oxidative polymerization of monohydric phenols and polyhydric phenols (Paragraph 13) and notes the use of solvent such as toluene (Paragraph 15) and the use of catalysts such as copper (I) oxide (Paragraph 15), meeting the requirements of the instant claims. While Carrillo does not specifically teach that the monohydric phenol is a 2-alkyl-6-aryl substituted phenol, that substitution pattern is allowed by Carrillo. Because the 2, 4, and 6 positions of the phenol are reactive, if only reactivity is desired at the 4 position, it would logically follow that the 2 and 6 positions be substituted, as Carrillo requires (Paragraph 8). Additionally, Tarkin-Tas teaches the use of 2-alkyl-6-phenylphenol in a poly(arylene ether) copolymer that is made using an oxidative polymerization (Paragraph 18) and it would have been obvious to have used this monomer for the reasons stated above in regard to claims 1, 3-4 and 7. It would further have been obvious prior to the effective filing date of the instant application to have substituted these positions with any of the substituents as disclosed by Carrillo. Carrillo teaches that mixtures of monohydric phenols may be used (Paragraph 13).
Regarding Claims 11 and 12,
Carrillo teaches that the capping reaction may be conducted on the polymerization reaction mixture containing the solvent and catalyst from the reaction, but may also be performed following solvent and catalyst removal (Paragraph 31), meeting the requirements of the instant claims.
Regarding Claims 14-15,
While Carrillo is silent on the steps forming an article, Carrillo does teach that compositions containing poly(arylene ethers) are often blended with other plastics to form a variety of products, including automotive parts, plumbing fixtures, and coated wire (Paragraph 1) and additionally teaches that the addition of poly(arylene ethers) to thermoset resins can make them less brittle (Paragraph 1), rendering the use of the polymer as disclosed by Carrillo which is a poly(arylene ether) in a thermoset composition to produce an article to have been obvious prior to the effective filing date of the instant application.
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.
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.
Claims 14 and 15 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 8, and 10 of U.S. Patent No. 12,503,593. Although the claims at issue are not identical, they are not patentably distinct from each other because both the instant application and the reference application require a capped poly(arylene ether) copolymer which must contain a monomer with 2-alkyl-6-aryl substitution that is capped with a reactive group and also contains a diphenol group and is used to form a cured article comprised of the aforementioned polymer.
Response to Arguments
Applicant's arguments filed 5/18/2026 have been fully considered but they are not persuasive for the following reasons.
On pages 8 and 9, the applicant argues that Carrillo does not explicitly teach the required structure. The examiner notes that the rejection has been modified to a 103 rejection, rendering this argument to be moot.
On page 9, the applicant argues that the structures defined by Carrillo are broad. The examiner notes that broad disclosures are not inherently disqualified simply for teaching a broad range of options. However, the examiner also notes that Tarkin-Tas (WO 2018194797 and US 20200172729) are now cited in the rejection and specifically teach the 2-alkyl-6-arylphenol monomer, which renders this argument to be moot.
On pages 9 and 10, the applicant argues that Carrillo does not exemplify 6-aryl monomers. The examiner points out that references must be considered for the totality of their teachings, which does not limit the teachings simply to the exemplified examples. Carrillo discloses that the 6-aryl-substituted monomers are expressly taught by Carrillo as noted in the rejection and further, through the addition of Tarkin-Tas, explicitly taught along with motivations for using such monomers including decreased viscosity and improved polymer solubility.
Finally, on pages 10 and 11, the applicant argues unexpected results and provides an affidavit mentioning these results. The examiner appreciates the submission of this affidavit as well as the work that would be conducted in order to provide this information. However, the examiner notes that the properties pointed to in the affidavit are not present as limitations of the claims and are therefore not afforded patentable weight. Further, the affidavit notes that one of the unexpected improvements is related to resin flow, which the examiner interprets to mean a lowered viscosity. This change to the polymer is noted by the Tarkin-Tas reference used in the rejection as being a noted effect of using phenyl-substituted phenols as monomers and as such, it would not appear to be unexpected when using such monomers in the poly(arylene ether polymers).
In summary, the applicant’s arguments are mostly directed towards the previous 102 rejection, which has been changed to a 103 rejection in the current rejection and are no longer relevant. While the applicant cites unexpected results, these properties are not limitations of the claims and further, one of the cited properties appears to be a decrease in viscosity that has been noted in the prior art as a reason for using the 2-alkyl-6-phenylphenol monomer required by the instant claims. As a result, the rejection is maintained.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ADAM J BERRO whose telephone number is (703)756-1283. The examiner can normally be reached M-F 8:30-5.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Heidi Kelley can be reached at 571-270-1831. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/A.J.B./Examiner, Art Unit 1765 /HEIDI R KELLEY/Supervisory Patent Examiner, Art Unit 1765
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