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 .
Response to Arguments
Regarding claim 6, the applicant's arguments filed 12/24/2025 have been fully considered but they are not persuasive.
The Applicant argues that Carrillo fails to teach combining two different monohydric phenols and a polyphenol having a functionality greater than 2.
However, in the previous office action, the Examiner cited 2,6-bis(2-hydroxy-5-methylbenzyl)-4-methyl phenol as the multifunctional phenol of Carrillo (Paragraph [0008]). This multifunctional phenol reads on the limitation of “wherein the multifunction phenol or polyphenol have a functionality greater than 2.”
The Applicant also argues that as stated in the specification, synthesis of poly(arylene ether) copolymer by oxidative polymerization of monohydric phenols yields the polyarylene ether copolymer and the diphenoquinone side product. The Applicant argues that the teachings of Hays necessarily result in the diphenoquinone side product being present in the teachings of Carrillo.
It is acknowledged that Carrillo does not state any methodology for removing diphenoquinone and as it stands Carrillo could include diphenoquinone residues in the resulting polyarylene copolymer.
Claim 1 is now rejected over Carrillo in view of White and Fishburn which address diphenoquinone residues.
The Applicant also argues that it would not have been “obvious to try” two monohydric phenols together because Carrillo never teaches copolymerizing two different monohydric phenols together.
However, the Examiner notes that Carrillo teaches equally suitable alternatives A1 and 2,6-dimethylphenol. 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. The argument is not that it is “obvious to try” combining A1 and 2,6 dimethylphenol. It is obvious to combine two compositions because each composition is taught by the prior art to be useful for the same purpose. See MPEP 2144.06.
This also applies to the Applicant’s arguments surrounding claim 7. It is obvious to use both polyhydric phenols taught in Carrillo as they are taught as equally suitable alternatives.
The Applicant further argues that the advantages provided by the secondary reference is not needed or relevant to the primary reference.
Specifically the Applicant argues that Hay teaches the low intrinsic viscosity is a result of the phenols having only a reactive para position. Carrillo discloses that the ratio of monohydric to polyhydric phenol is what contributes to achieving the target intrinsic viscosity. Carrillo also teaches a polyhydric phenol in the synthesis and some of the hydroxyl groups are not in para positions. Therefore, the Applicant argues that Hay teaches the viscosity of the polymer is based on the structure of the monomer and Carrillo teaches that the viscosity is based on the molar ratio of monohydric to polyhydric phenol.
However, the Examiner notes that Yaeger teaches the monohydric phenols of Hay are suitable as monohydric phenols for the composition of Yaeger despite the additional phenols Yaeger not necessarily only being phenols with a reactive para position (Yaeger, Paragraph [0016]). Therefore, it would have been obvious to use the monohydric phenol of Hay in the composition of Carrillo as Carrillo also teaches a low viscosity polyarylene ether that is suitable for circuit board applications (Abstract, Paragraph [0001]), and the monohydric phenols of Hay are used in the low viscosity polyarylene ether suitable for circuit board applications in Yaeger.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1, 2-5, 7, and 16-17 are rejected under 35 U.S.C. 103 as being unpatentable over Carrillo US 200701060501A in view of White EP 0 822 222 A2 and Fishburn 20120214929A1.
Regarding claims 1-5 and 16-17, Carrillo teaches that a polyfunctional poly(arylene ether) can be synthesized from oxidatively copolymerizing a monohydric phenol and a polyhydric phenol (Abstract). This reads on the claimed “oxidative polymerization.” Carrillo also teaches the monohydric phenol has a structure of
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(henceforth referred to as A1). (Paragraph [0005]). This structure corresponds to the claimed structure where Q1=Z1; Q2=Z2; and the bonds extending beyond the brackets each connect to hydrogen. Q1 and Q2 as defined at [0005] include substituents reading on the claimed Z1 and Z2, and Carrillo does not require that both Q1’s and/or both Q2’s are simultaneously methyl. Specifically Carrillo teaches Q1 is independently halogen, primary or secondary C1 -C12 alkyl, C2-C12 alkenyl, C3 -C12 alkenylalkyl, C2-C12 alkynyl, C3 -C12 alkynylalkyl, C1 -C12 aminoalkyl, C1 -C12 hydroxyalkyl, C6-C12 aryl (including phenyl), C1-C12 haloalkyl, C1-C12 hydrocarbonoxy, C1 -C12 halohydrocarbonoxy wherein at least two carbon atoms separate the halogen and oxygen atoms, or the like; and wherein each occurrence of Q2 is independently hydrogen, halogen, primary or secondary C1 -C12 alkyl, C2-C12 alkenyl, C3-C12 alkenylalkyl, C2 -C12 alkynyl, C3 -C12 alkynylalkyl, C1-C12 aminoalkyl, C1-C12 hydroxyalkyl, CcC12 aryl (including phenyl), C1-C12 haloalkyl, C1-C12 hydrocarbonoxy, C1 -C12 halohydrocarbonoxy wherein at least two carbon atoms separate the halogen and oxygen atoms, or the like. This encompasses the limitations of Z1 and Z2 as defined by claims 2, 5, 16 and 17. Therefore this reads on the claimed structure of formula 1.
Carrillo also teaches that the monohydric phenol can be 2,6-dimethylphenol. (Paragraph [0005]). The structures of A1, 2,6 dimethylphenol are recited in parallel as equally suited alternatives. 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. Therefore, it would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to use both a monohydric phenol of the structure A-1 and 2,6, dimethylphenol as the monohydric phenol. This reads on the claimed first and second monohydric phenol.
Carrillo teaches that the polyhydric phenol can be 2,6-bis(2-hydroxy-5-methylbenzyl)-4-methyl phenol (Paragraph [0008]). This compound falls within the scope of formula (8-1) presented in claim 4 where n=2, a=1, b=1, and Ra and Rb = C1 alkyl. Therefore, this reads on the claimed polyphenol comprising a novolac. It would have been obvious to one of ordinary skill in the art at the time of filing to select a mixture of 2,6-dimethylphenol as the monohydric phenol and 2,6-bis(2-hydroxy-5-methylbenzyl)-4-methyl phenol as the polyhydric phenol, as they are expressly identified as being suitable for this purpose. Selecting known materials based on their suitability for their intended use is prima facie obvious. See MPEP 2144.07.
Carrillo is silent on the amount of diphenoquinone in the composition. However, White teaches residual diphenoquinone in a polyphenylene ether compositions result in discoloration and yellowing (Page 2 Lines 15-29). White also teaches that it would be desirable to decrease the color number of polyphenylene ether resins by a substantial amount during melt processing and that decreased color would maximize the utility of the resin in various applications in which color is un- desirable (Page 2 Lines 39-41).
Fishburn teaches diphenoquinone residues can be removed through precipitation of the polyarylene ether in a solvent or solvent mixture in which the polyarylene ether is insoluble and the diphenoquinone is soluble (Paragraph [0019]). It would have been obvious to one of ordinary skill in the art at the time of filing to remove the diphenoquinone byproducts from the composition of Carrillo using the precipitation method taught in Fishburn for the advantage of reducing the yellowing of the resulting polymer and increasing the number of applications the polyphenylene ether resin is suitable for (as taught in White). Therefore, Carrillo in view of White and Fishburn reads on the limitations of free of diphenoquinone residues.
Regarding claim 7, Carrillo also teaches that the polyhydric phenol can also be 1, 1, 1-tris(3,5-dimethyl-4-hydroxyphenyl)ethane (Paragraph [0008]). Both 2,6-bis(2-hydroxy-5-methylbenzyl)-4-methyl phenol and 1, 1-tris(3,5-dimethyl-4-hydroxyphenyl)ethane are recited in parallel as equally suited alternatives. 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. Therefore, it would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to use both as the polyhydric phenol. 1, 1, 1-tris(3,5-dimethyl-4-hydroxyphenyl)ethane reads on the claimed structure 10a where Re, Rc, and Rd, are all C1 alkyl, Re’, Rc’, and Rd’ are all hydrogens and Rf is a C1 alkyl.
Claim 6 is rejected under 35 U.S.C. 103 as being unpatentable over Carrillo US 20070106051A in view of White EP 0 822 222 A2 and Fishburn 20120214929A1 in further view of Yeager US 20060038324 and Hays US 3,306,875.
Regarding claim 6, Carrillo does not explicitly state structure of A-1.
Hays teaches suitable monohydric phenols used in oxidative polymerization to form polyarylene ethers (Equation 1 and col. 6 Lines 5-15). Hays teaches one such suitable monohydric phenol is 2-methyl-6-phenylphenol (Col . 8 Line 47).
Yeager teaches that the monohydric phenols of Hays can be used to form polyarylene ethers with a viscosity from 0.05-6 dl/G at 25C in chloroform (Paragraph [0016] and [0026]). Yeager also teaches these polyarylene ethers can be used in circuit board applications (Paragraph [0001]).
Carrillo’s polyarylene ether has a low viscosity ranging from 0.04-0.3 dL/g, this low viscosity is suitable for circuit board applications (Abstract, Paragraph [0001]). It would have been obvious to one of ordinary skill in the art at the time of filing to use a monohydric alcohol of Hays in the composition of Carrillo because the monohydric alcohols of Hays are known to be suitable for the synthesis of low viscosity polyarylene ethers in circuit board applications, as shown in Yeager. It would have been obvious to select 2-methyl-6-phenylphenol as the monohydric alcohol of Hays because it has been established that selection of a known material based on its suitability for its intended use is prima facie obvious. See MPEP 2144.07. See also In re Susi, 440 F.2d 442, 445 (CCPA 1971).
Claims 8 is rejected under 35 U.S.C. 103 as being unpatentable over Carrillo US 20070106051A in view of White EP 0 822 222 A2 and Fishburn US 20120214929A1 in further view of Braidwood US 20080246173 A1.
Regarding claim 8, Carrillo teaches the polyarylene ether has a low intrinsic viscosity from 0.04-0.3 dL/g (Abstract). Carrillo also teaches the polyarylene ether with low viscosity is used in circuit board applications (Paragraph [0001]). Braidwood teaches a polyarylene ether Is formed from oxidative polymerization of monohydric phenol and optionally a polyhydric phenol (Paragraph [0040]). Braidwood also teaches the viscosity of the composition is 0.03-1 dL/g (Paragraph [0045]). Braidwood also teaches the polyarylene ether can be used to form circuit boards (Paragraph [0001]).
Braidwood also teaches the polyarylene ether can be capped with a capping agent through an acylation reaction where the capping agent is methacrylic anhydride (Paragraph [0042]). This reads on the claimed methacrylate.
It would have been obvious to combine the teachings of Carrillo and Braidwood and use the capping agent of Braidwood in the polyarylene ether of Carrillo because Braidwood teaches a suitable capping agent for a similar polymer used in a similar application.
Conclusion
THIS ACTION IS MADE FINAL. 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 LILY K SLOAN whose telephone number is (703)756-5875. The examiner can normally be reached Monday-Friday 9:00-5:30 ET.
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/LILY K SLOAN/Examiner, Art Unit 1762
/ROBERT S JONES JR/Supervisory Patent Examiner, Art Unit 1762