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 .
Claims 1-8 and 16-17 are pending as amended on December 19, 2025. Claims 9-15 stand withdrawn from consideration. Support for amended claims 1-2 and 4-7 is found in original claims 1-2 and 4-7. Claims 4 and 7 have been amended into independent form including all of the limitations of claim 1 and are therefore allowable.
The new grounds of rejection set forth below were necessitated by the amendment making claim 6 dependent on claim 2. The other rejections below were solely modified to reflect the claim amendments. Therefore, this action is properly made final.
Any objections and/or rejections made in the previous Office action and not repeated below are hereby withdrawn.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.
Response to Arguments
Applicant’s arguments filed December 19, 2025 have been fully considered.
With respect to claim 1, Applicant argues (page 13-14) that a person of ordinary skill would not be guided by the teaching of Carrillo (US 2013/0197167 A1) in view of Delsman (US 2007/0208144 A1) to arrive at the oligomers recited in claim 1 for the reasons described below.
Applicant argues (page 13) that Delsman teaches a branching unit, but that the branching unit is never incorporated into a polymer or oligomer and one would therefore need to guess where and how the branching unit is incorporated into a copolymer. While Delsman does not exemplify a polysiloxane comprising a branching unit, this does not negate a finding of obviousness under 35 USC 103 since a preferred embodiment such as an example is not controlling. Rather, all disclosures “including unpreferred embodiments” must be considered. In re Lamberti 192 USPQ 278, 280 (CCPA 1976) citing In re Mills 176 USPQ 196 (CCPA 1972). Therefore, it would have been obvious to one of ordinary skill in the art to utilize a polysiloxane with a branching unit given that Delsman and Carrillo teach one. The rejection was based on random incorporation of the branching unit of Delsman into the polysiloxane of Carrillo and is sufficient to teach the claimed structure. For example, the monomer used to produce a branching unit corresponding to formula (5a) is CH3SiCl3. During the synthesis of the polysiloxane each chlorine atom would be expected to be replaced with an oxygen atom as the start of a polysiloxane segment. Carrillo teaches that the polysiloxane block of the poly(arylene ether) copolymer can comprise about 10 to about 100 siloxane repeating units (Carrillo, [0004]). One would therefore understand that the total number of siloxane repeating units in the siloxane oligomer should be about 10 to about 100. One would therefore produce a polysiloxane where the sum of the k subscripts in formulas (5a) is about 10 to about 100. In addition, given that the end group of Carrillo and Delsman has a silicon atom and a branching unit derived from CH3SiCl3 contributes an oxygen atom, each k is at least 1. Because each k must be at least 1, the maximum k possible is 98 (100-(2*1)). A range of k is 1-98 falls within the claimed range of 1-100.
Applicant argues (page 13) that neither of Carrillo and Delsman teach a siloxane oligomer in combination with monomers. “Monomers” is taken to mean the monomers from which the branching units are derived. It is noted that the features upon which applicant relies (i.e., a siloxane oligomer in combination with monomers) 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). Claim 1 does not require having a monomer in combination with a siloxane oligomer, rather claim 1 is drawn to a poly(arylene ether) copolymer that is derived from siloxane oligomers comprising branch points according to formula (5a) and/or (5b). Both Delsman and Carrillo teach branched polysiloxanes. Delsman teaches synthesizing a branched polysiloxane by including the CH3SiCl3 or SiCl4 monomers of Delsman during the synthesis of the polysiloxane (Delsman, [0117]). Similarly, Carrillo teaches that the polysiloxanes can have branched structures (Carrillo, [0012]).
Applicant argues (pages 13-14) that the combined teachings of Carrillo and Delsman fail to teach the structure of the polysiloxane oligomer for the three reasons discussed below. Examiners must consider all claim limitations when determining patentability of an invention over the prior art. In re Gulack, 703 F.2d 1381, 1385, 217 USPQ 401, 403-04 (Fed. Cir. 1983).
First, Applicant argues (page 13) that Delsman teaches a branching unit that is different than the oligomer recited in claim 1. Applicant first argues that Delsman does not teach [OSiR2] as a branching unit. This argument is not persuasive because the claimed formula (5a) and formula (5b) oligomers do not comprise [OSiR2] as a branching unit. The [OSiR2] units of the instant oligomers correspond to the repeat units of Delsman and Carrillo. In order for the branching units to branch there can be at most a single R, as in the case of formula (5a). Both Delsman and Carrillo teach [OSiR2] siloxane repeating units but, as in instant formula (5a) and (5b), these repeating units with two R groups are not branching units.
Second, Applicant argues that the claimed siloxane repeating units include R groups, but these R groups are not present in the branching unit of Delsman. This argument is not persuasive because Delsman teaches the claimed R group on the branching unit of formula (5a) and the claimed branching unit in formula (5b) has no R groups. Like the claimed branching units, Delsman teaches branching units with one (
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) or zero (
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) R groups. Delsman’s R16 corresponds to the R on the branching unit of formula (5a) and is a C1 alkyl (CH3SiCl3 corresponds to R16 is methyl).
Third, Applicant argues that Carrillo does not teach two polysiloxane groups on either side of a central Si atom, as depicted in claim 1 (formula (5a)). Applicant points to the
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block taught by Carrillo; however, the rejection was not based on this linear block. One cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).
The rejection is based on incorporating the branching point of Delsman into the branched siloxane oligomer of Carrillo. One of ordinary skill would expect two polysiloxane groups on either side of the central silicon atom (silicon atom from branching unit) because one would expect a branching unit to have at least two polysiloxane branches.
With respect to claims 2, 5, and 16-17, Applicant argues (page 14) that the rejection relies on modifying Carrillo to improve solubility in non-halogenated solvents, but the instant application seeks to improve dielectric performance of thermosetting materials. MPEP section 2144, subsection IV states, “The reason or motivation to modify the reference may often suggest what the inventor has done, but for a different purpose or to solve a different problem. It is not necessary that the prior art suggest the combination to achieve the same advantage or result discovered by applicant. See, e.g., In re Kahn, 441 F.3d 977, 987, 78 USPQ2d 1329, 1336 (Fed. Cir. 2006).” In this case, one would have been motivated to substitute the 2,6-dimethylphenol of Carrillo with the combination of 2,6-dimethylphenol and 2-methyl-6-phenylphenol taught by Yeager & Stone (US 2008/0076884-A1) 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 the oxidative copolymerization of Carrillo is performed in benzene, toluene, xylenes, and mixtures thereof (Carrillo, [0017]) and Carrillo teaches that reducing solubility in aromatic hydrocarbon solvents is undesirable (Carrillo, [0011]).
In response to applicant's argument (page 14) that the examiner's conclusion of obviousness is based upon improper hindsight reasoning, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971). In this case, the conclusion of obviousness is based solely on the disclosures of Carrillo, Delsman, and Yeager & Stone and does not rely on Applicant’s disclosure. As discussed in the previous paragraph, one would have been motivated to substitute the 2,6-dimethylphenol of modified Carrillo with the combination of 2,6-dimethylphenol and 2-methyl-6-phenylphenol taught by Yeager & Stone (US 2008/0076884-A1) in order to improve solubility in non-halogenated solvents, such a benzene, toluene, and xylenes.
Claim Objections
Claims 5-6 and 16-17 are objected to because of the following informalities:
Claims 5-6 and 16-17 contain substituent names that should contain spaces. For example, “C1-6alkyl” in line 3 of claim 5 should read “C1-6 alkyl.”
Appropriate correction is required.
Claim Rejections - 35 USC § 112
Claims 2, 5-6, and 16-17 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.
Claim 2 contains the limitation “each occurrence of Z1 independently comprises” (line 5). The alternatives listed represent improper Markush groups because use of the phrase “comprises” indicates that the groups are open rather than closed. This can be corrected by replacing “independently comprises” with “is independently selected from the group consisting of.” Claims 5 and 16-17 are rejected by virtue of dependency on claim 2 because they do not correct the issue.
Claims 5-6 and 16-17 contain substituents in parentheses. For example, line 4 of claim 5 recites “C1-3alkyl(C3-12cycloalkyl).” It is unclear if the terms in parentheses are substituents included in the Markush group or if the terms in parentheses redefine the adjacent terms. One way to correct this issue is to amend the Markush groups such that the desired alternatives are listed without parentheses. Claims 16-17 are rejected by virtue of dependency on claim 5 because they do not correct the issue.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 6 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Claim 6 contains the limitation “one occurrence of Z1 of the first monohydric phenol is methyl; and the other occurrence of Z1 of the first monohydric phenol is methyl, …” in lines 3-4. Claim 6 depends from claim 2 but does not require all of the limitations of claim 2 because claim 2 states that “each occurrence of Z1 are not simultaneously methyl.”
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Claim Rejections - 35 USC § 103
Claims 1 and 3 stand rejected under 35 U.S.C. 103 as being unpatentable over Carrillo (US 2013/0197167 A1) in view of Delsman (US 2007/0208144 A1), as set forth in the 9/24/2025 Office action.
Claims 2, 5, and 16-17 stand rejected under 35 U.S.C. 103 as being unpatentable over Carrillo (US 2013/0197167 A1) in view of Delsman (US 2007/0208144 A1) as applied to claim 1 above, and further in view of Yeager & Stone (US 2008/0076884-A1), as set forth in the 9/24/2025 Office action.
Claim 8 stands rejected under 35 U.S.C. 103 as being unpatentable over Carrillo (US 2013/0197167 A1) in view of Delsman (US 2007/0208144 A1) as applied to claim 1 above, and further in view of Yeager (US 2005/0187373 A1), as set forth in the 9/24/2025 Office action.
Claim 6 is rejected under 35 U.S.C. 103 as being unpatentable over Carrillo (US 2013/0197167 A1) in view of Delsman (US 2007/0208144 A1) and Yeager & Stone (US 2008/0076884-A1), as applied to claim 2 in the 9/24/2025 Office action.
Modified Carrillo teaches the poly(arylene ether) copolymer of claim 2 wherein the first monohydric phenol comprises 2-methyl-6-phenylphenol. A first monohydric phenol comprising 2-methyl-6-phenylphenol corresponds to one Z1 of the first monohydric phenol is methyl and the other occurrence of Z1 is an unsubstituted phenyl.
Allowable Subject Matter
Claims 4 and 7 are allowed.
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 is Carrillo (US 2013/0197167 A1) in view of Delsman (US 2007/0208144 A1).
Carrillo in view Delsman teaches a poly(arylene ether) copolymer that is a product of oxidative copolymerization of monomers comprising a first monohydric phenol, a second monohydric phenol different from the first monohydric phenol, and a siloxane oligomer according to formulas (5a) and/or (5b), as discussed above for claim 1. Carrillo further teaches the following siloxane oligomer:
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where n is about 10 to about 100 (Carrillo, [0030]).
While this formula reads on the formulas presented in claim 4 and claim 7, Carrillo does not fairly suggest using a combination of two siloxane oligomers in the poly(arylene ether). Therefore, a combination of the siloxane oligomers of formulas (5a) or (5c) together with a siloxane oligomer of claim 4 or claim 7 is not fairly suggested by Carrillo. The examiner is not aware of a prior art disclosure of this combination of siloxane oligomers in a poly(arylene ether) copolymer.
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 AUDRA DESTEFANO whose telephone number is (703)756-1404. The examiner can normally be reached Monday-Friday 9-5.
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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.
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/AUDRA J DESTEFANO/Examiner, Art Unit 1766
/RANDY P GULAKOWSKI/Supervisory Patent Examiner, Art Unit 1766