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 .
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 June 15, 2026 has been entered.
Claims 1-20 are pending as amended on June 15, 2026. Amended claims 1, 4, and 7 are supported by [0012], [0019], and [0029]. Claims 18-20 are new and supported by claim 1. Claims 9-15 stand withdrawn from consideration.
Any objections and/or rejections made in the previous Office action and not repeated below are hereby withdrawn.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 the action can be found in a prior Office action.
Election/Restrictions
Newly submitted claim 20 depends from claim 1 and requires that the structural unit derived from the siloxane oligomer is of formula (5c). The restriction requirement mailed on 7/08/2025 required the election of a single species as the siloxane oligomer. Applicant elected the species where the siloxane oligomer is formula (5a) or formula (5b) in the reply filed on 7/08/20205. Accordingly, claim 20 is withdrawn from consideration as being directed to a non-elected invention.
Response to Arguments
Applicant's arguments filed June 15, 2026 have been fully considered.
Claim 1 has been amended to require that the structural unit derived from the siloxane oligomer comprises at least one of formulas (5a) to (5c). Each of these structural units contains 1-2 unreacted hydroxyl groups. Carrillo (US 2013/0197167 A1) does not suggest a copolymer where the siloxane oligomer residues contain unreacted hydroxyl groups and one would not expect to obtain such a copolymer based on Carrillo’s disclosure because Carrillo’s copolymer is obtained by oxidative copolymerization ([0009]). One would not expect unreacted hydroxyl groups after modifying the siloxane oligomer by oxidative copolymerization with the monohydric phenols to obtain the poly(arylene ether) copolymer because one would expect most hydroxyl groups to be modified with the monohydric phenols. Therefore, the rejections of claims 1-3, 5-6, 8, and 16-17 over modified Carrillo have been withdrawn. However, upon further consideration, a new ground of rejection is made in view of Delsman (US 2007//0208144 A1).
The affidavit under 37 CFR 1.132 filed June 15, 2026 is relevant to the new rejection over Delsman. Applicant argues (page 1-2 of the affidavit) that the prior art references do not recognize or describe the technical consequences of using branched siloxane oligomers instead of linear siloxanes and do not suggest effects on processing behavior, network formation, and thermal resistance. Applicant argues (page 3 of the affidavit) that the use of branched siloxane oligomers provides meaningful and non-trivial advantages that are not inherent to or predictable from linear siloxane systems. This argument is not persuasive because the rejection relies on branched siloxanes taught by Delsman, not linear siloxanes. In particular, it would have been obvious to one of ordinary skill to have selected a branched siloxane because Delsman teaches it. The fact that the inventor has recognized another advantage which would flow naturally from following the suggestion of the prior art cannot be the basis for patentability when the differences would otherwise be obvious. See Ex parte Obiaya, 227 USPQ 58, 60 (Bd. Pat. App. & Inter. 1985). If applicant wishes to show that the advantages of branched siloxanes are unexpected, Applicant must provide evidence that these results are unexpected. See MPEP 716.02.
Applicant similarly argues (page 12-13 of the arguments) that the selection of a branched siloxane would not be an obvious design choice because the cited references do not recognize the effects of selecting a branched siloxane. This argument is not persuasive because the rejection relies on branched siloxanes, not linear siloxanes. It would have been obvious to one of ordinary skill to have selected a branched siloxane because Delsman teaches it. The fact that the inventor has recognized another advantage which would flow naturally from following the suggestion of the prior art cannot be the basis for patentability when the differences would otherwise be obvious. See Ex parte Obiaya, 227 USPQ 58, 60 (Bd. Pat. App. & Inter. 1985). In addition, while Applicant argues that these performance advantages would not be expected, Applicant has not provided evidence of unexpected results. See MPEP 716.02.
Applicant also argues (page 13, paragraph 1) that there would have been no reasonable expectation that using a branched siloxane oligomer would lead to the described advantages. It is noted that the features upon which applicant relies (i.e., enhanced thermal resistance) are not recited in the rejected claim(s). Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993). None of the claims limit the thermal resistance of the copolymer.
Claim Objections
Claims 1-2, 4, 7, and 16 are objected to because of the following informalities:
In claim 1, line 3, “from first” should read “from the first.”
In claim 1, 6th to last line, it is suggested that the line should end with a semicolon rather than a period to be consistent with the rest of the list.
In claim 2, lines 8 and 15, it is suggested that the lines should end with a semicolon rather than a period to be consistent with the rest of the list.
In claim 4, lines 4 and 6, “the a structural unit” should read “the structural unit.”
In claim 4, line 17 (R1 description), it is suggested that the line should end with a semicolon rather than a period to be consistent with the rest of the list.
In claim 7, line 5-6, “a a structural unit” should read “a structural unit.”
In claim 7, line 6, “the a structural unit” should read “the structural unit.”
In claim 7, line 17 (R1 description), it is suggested that the line should end with a semicolon rather than a period to be consistent with the rest of the list.
In claim 16, line 5, “withC1-3 alkyl” should read “with C1-3 alkyl.”
Appropriate correction is required.
Claim Rejections - 35 USC § 103
Claims 1, 3, and 18-19 are rejected under 35 U.S.C. 103 as being unpatentable over Delsman (US 2007/0208144 A1).
Delsman teaches poly(arylene ether)-polysiloxane block copolymers prepared by reacting a poly(arylene ether), a hydroxylaryl-terminated polysiloxane, and an activated aromatic carbonate ([0114], [0122]). Delsman’s poly(arylene ether)-polysiloxane block copolymer reads on a poly(arylene ether) copolymer.
Suitable poly(arylene ether) blocks include copolymers of 2,6-dimethyl-1,4-phenylene ether units and 2,3,6-trimethyl-1,4-phenylene ether units ([0045] and [0122]). The 2,6-dimethyl-1,4-phenylene ether units and 2,3,6-trimethyl-1,4-phenylene ether units read on structural units derived from a first monohydric phenol and a second monohydric phenol that is different from the first monohydric phenol. The 2,3,6-trimethyl-1,4-phenylene ether units read on wherein the second monohydric phenol is 2,3,6-trimethyl phenol (claim 3).
Delsman’s hydroxyaryl-terminated polysiloxanes are described in [0117]. As a specific example, Delsman teaches a polysiloxane with the following structure ([0118]):
PNG
media_image1.png
116
420
media_image1.png
Greyscale
wherein n is 5-200.
The polysiloxane shown above does not comprise a branch point, as shown in the claimed (5a) and (5b) formulas.
However, Delsman teaches that the polysiloxane may comprise one or more of the following branching units ([0117]):
PNG
media_image2.png
163
57
media_image2.png
Greyscale
where each occurrence of R16 is a hydrogen, C1-C12 hydrocarbyl, or a C1-C12 halohydrocarbyl. Delsman teaches that the branches result from the use of one or more monomers such as CH3SiCl3, CH3Si(OCH2CH3)3, SiCl4, and Si(OCH2CH3)4 during synthesis of the polysiloxane ([0117]). The branching point on the left is derived from CH3SiCl3 or CH3Si(OCH2CH3)3 and corresponds to the branching point in formula (5a) where R is a methyl group (claim 18). The branching point on the right is derived from SiCl4 or Si(OCH2CH3)4 and corresponds to the branching point in formula (5b) (claim 19).
It would have been obvious to one of ordinary skill to have prepared a polysiloxane with one branching point derived from CH3SiCl3, CH3Si(OCH2CH3)3, SiCl4, or Si(OCH2CH3)4 because Delsman teaches it. In particular, it would have been obvious to prepare a polysiloxane comprising one branch point together with the repeating units and terminal units exemplified by
PNG
media_image1.png
116
420
media_image1.png
Greyscale
. The resulting polysiloxane corresponds to a siloxane oligomer where R is a C1 alkyl; R1 is a divalent C3 aliphatic group; p, q, r, and s (in the case of formula (5b)) are 1; M is a C1 alkoxy; and m is 1. Delsman’s exemplified n=5-200 corresponds to the sum of the k values is 5-200. In the case of a
PNG
media_image2.png
163
57
media_image2.png
Greyscale
branch point, this corresponds to each k is about 1-67 (evenly dividing the number of repeating units by 3). In the case of the
PNG
media_image2.png
163
57
media_image2.png
Greyscale
branch point, this corresponds to each k is about 1-50 (evenly dividing the number of repeating units by 4).
Delsman does not anticipate a copolymer where the structural unit derived from the siloxane oligomer comprises at least 1 (formula (5a)) or 2 (formula (5b)) unreacted hydroxyl groups.
However, Delsman teaches that the block architecture of the copolymer may be controlled via the number of hydroxy groups on the poly(arylene ether), the number of moles of activated carbonate to total moles of hydroxy groups on the poly(arylene ether) and polysiloxane, the use of an endcapping agent, and other reaction conditions ([0121]). Delsman further suggests a range of 0.5-2 moles of activated aromatic carbonate per two moles of total hydroxy groups contributed by the poly(arylene ether) and the hydroxylaryl-terminated polysiloxane ([0119]). It would have been obvious to one of ordinary skill to have used any activated aromatic carbonate content in the range of 0.5-2 moles per two moles of total hydroxy groups contributed by the poly(arylene ether) and the hydroxylaryl-terminated polysiloxane because Delsman teaches it, including an activated carbonate content that results in the claimed structural unit derived from the siloxane oligomer. This range corresponds to polysiloxane residues in which at least half and up to all of the polysiloxane hydroxyl groups are reacted. This number of hydroxyl groups on the polysiloxane residue overlaps with the number required by the structures of formula (5a) (requires 33-66% of hydroxyl groups remaining) and formula (5b) (requires 50-75% of hydroxyl groups remaining). It would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to have selected the overlapping portion of the ranges disclosed by the reference because selection of overlapping portion of ranges has been held to be a prima facie case of obviousness. See MPEP § 2144.05.I.
Claims 2, 5-6, and 16-17 are rejected under 35 U.S.C. 103 as being unpatentable over Delsman (US 2007/0208144 A1) as applied to claim 1 above, and further in view of Yeager & Stone (US 2008/0076884-A1).
Delsman teaches the poly(arylene ether) copolymer of claim 1 wherein the first monohydric phenol consists of 2,6-dimethylphenol. The compound 2,6-dimethylphenol does not read on formula (1) as defined in claims 2, 5, and 16-17 because each occurrence of Z1 is methyl.
However, Yeager & Stone teach poly(arylene ether) copolymers with improved solubility in non-halogenated solvents compared to poly(2,6-dimethyl-1,4-phenylene ether)s of comparable molecular weight (Yeager & Stone, [0018]). Yeager & Stone exemplify copolymers of 2,6-dimethylphenol and 2-methyl-6-phenylphenol (Yeager & Stone, [0045]) and teach benzene, toluene, and xylenes as examples of solvents (Yeager & Stone, [0039] and [0045]).
It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to have substituted the 2,6-dimethylphenol of Delsman with the combination of 2,6-dimethylphenol and 2-methyl-6-phenylphenol taught by Yeager & Stone in order to improve solubility in non-halogenated solvents, such a benzene, toluene, and xylenes. One would have been motivated to improve solubility in these solvents because Delsman teaches preparing the poly(arylene ether)-polysiloxane block copolymer in solvents such as benzene, toluene, and xylenes ([0114]). This substitution leads to a first monohydric phenol consisting of 2,6-dimethylphenol and 2-methyl-6-phenylphenol.
A first monohydric phenol comprising 2-methyl-6-phenylphenol reads on the first monohydric phenol comprises the formula (1) wherein each occurrence of Z1 is independently an unsubstituted C1 primary hydrocarbyl (methyl) or an unsubstituted secondary C6 hydrocarbyl (C6 aryl, phenyl) and each occurrence of Z2 is hydrogen. This reads on Z1 is an unsubstituted C1 alkyl or C6 aryl, each occurrence of Z1 are not simultaneously methyl and each occurrence of Z2 are not simultaneously methyl (claim 2, 5, and 16-17). It also reads one occurrence of Z1 of the first monohydric phenol is methyl and the other is an unsubstituted phenyl (claim 6).
Allowable Subject Matter
Claim 4 and claim 7 are allowed. Claim 8 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter:
As of the date of this office action, no prior art references, whether considered individually or in combination have been identified to anticipate or render obvious the claimed invention under 35 U.S.C. §102 or §103.
The closest prior art of record to claim 4 and claim 7 is Delsman (US 2007/0208144 A1).
As laid out for claim 1 above, Delsman teaches a poly(arylene ether) copolymer comprising a structural unit derived from a first monohydric phenol, a structural unit derived from a second monohydric phenol that is different from the structural unit derived from a first monohydric phenol, and a structural unit derived from a siloxane oligomer wherein the structural unit derived from the siloxane oligomer comprises formula (5a) or formula (5b). Delsman further teaches a residue of a siloxane oligomer with the structure shown below ([0126]):
PNG
media_image3.png
118
412
media_image3.png
Greyscale
where n is 5-200. This structure is identical to the siloxane residue shown in claim 7 and reads on the siloxane residue shown in claim 4 where E-1 is 5-200, R is a C1 alkyl, R1 is a divalent C3 aliphatic group, p and q are 1, M is C1 alkoxy, and m is 1.
Delsman differs from claim 4 and claim 7 in that Delsman does not suggest using a siloxane oligomer comprising both formula (5a) or (5b) and the structure recited in claim 4 or claim 7. Claim 4 and claim 7 are therefore allowable.
The closest prior art of record to claim 8 is Delsman (US 2007/0208144 A1) and Yeager (US 2005/0187373 A1, cited with 9/24/2026 Office action).
As laid out above, Delsman teaches the poly(arylene ether) copolymer of claim 1. Delsman does not teach a terminal functional group from those recited in claim 8.
Yeager teaches that a functionalized poly(arylene ether) having a pendant carbon-carbon double bond can be prepared by reacting the hydroxy end group of a poly(arylene ether) with a polyisocyanate compound followed by reaction with a polyfunctional group having a carbon-carbon double bond and a hydroxy, thiol, or amino group (Yeager, abstract). Yeager teaches that the functionalized poly(arylene ether) is useful as a curable component of a curable composition in which its carbon-carbon double bond copolymerizes with one or more olefinically unsaturated comonomers (Yeager, abstract). Yeager further teaches that poly(arylene ethers)s capped with polymerizable carbon-carbon double bonds are useful components of thermoset compositions, contributing desirable combinations of stiffness, toughness, and heat resistance (Yeager, [0001]). Yeager exemplifies a terminal functional group comprising (meth)acrylate (Yeager, [0017]).
Based on the disclosure of Yeager, one would have known that poly(arylene ethers)s capped with polymerizable carbon-carbon double bonds contribute desirable combinations of stiffness, toughness, and heat resistance in thermoset compositions (Yeager, [000]). However, one would not have been motivated to modify the copolymer of Delsman with the end groups of Yeager because Delsman does not suggest including the copolymer in a curable composition. One would also lack motivation to combine Yeager and Delsman because the only end capping agents taught by Delsman result in unreactive end groups (Delsman, [0062] and [0121]). Claim 8 is therefore allowable.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AUDRA DESTEFANO whose telephone number is (703)756-1404. The examiner can normally be reached Monday-Friday 9-5.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Randy Gulakowski can be reached at (571)272-1302. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/AUDRA J DESTEFANO/Examiner, Art Unit 1766
/RANDY P GULAKOWSKI/Supervisory Patent Examiner, Art Unit 1766
Prosecution Insights