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 .
Claim Status
Claims 1, 6, 11, 13, 14, 15, 17, 18, 19 and 20 are pending.
Priority
Acknowledgment is made of applicant's claim for priority under 35 U.S.C. 119(a)-(d) or (f), 365(a) or (b), or 386(a) based upon an application filed in China on 12/01/2020 (PCT/CN2020/133107). The claim for priority cannot be based on said application because the subsequent nonprovisional or international application designating the United States was filed more than twelve months thereafter and no petition under 37 CFR 1.55 or request under PCT Rule 26bis.3 to restore the right of priority has been granted.
Applicant may wish to file a petition under 37 CFR 1.55(c) to restore the right of priority if the subsequent application was filed within two months from the expiration of the twelve-month period and the delay was unintentional. A petition to restore the right of priority must include: (1) the priority claim under 35 U.S.C. 119(a)-(d) or (f), 365(a) or (b), or 386(a) in an application data sheet, identifying the foreign application to which priority is claimed, by specifying the application number, country (or intellectual property authority), day, month, and year of its filing (unless previously submitted); (2) the petition fee set forth in 37 CFR 1.17(m)(3); and (3) a statement that the delay in filing the subsequent application within the twelve-month period was unintentional. The petition to restore the right of priority must be filed in the subsequent application, or in the earliest nonprovisional application claiming benefit under 35 U.S.C. 120, 121, 365(c), or 386(c) to the subsequent application, if such subsequent application is not a nonprovisional application. The Director may require additional information where there is a question whether the delay was unintentional. The petition should be addressed to: Mail Stop Petition, Commissioner for Patents, P.O. Box 1450, Alexandria, Virginia 22313-1450.
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 and 7-10 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.
Regarding claims 1-5 and 7-10, the phrase” preferably" renders the claim indefinite because it is unclear whether the limitation(s) following the phrase are part of the claimed invention. See MPEP § 2173.05(d).
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim 1 is rejected under 35 U.S.C. 103 as being unpatentable over Chowdhury et al (US 2020/0385519 A1; herein ‘Chowdhury’).
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Chowdhury teaches the capped poly(arylene ether) copolymer can have can be a copolymer having the following formula:
wherein Q2 is independently hydrogen, halogen, unsubstituted or substituted C1-C12 hydrocarbyl provided that the hydrocarbyl group is not tertiary hydrocarbyl [p. 0035].
Chowdhury teaches the capped poly(arylene ether) copolymer is formed by the reaction of an uncapped poly(arylene ether) copolymer, for example an uncapped poly(phenylene ether) copolymer, with a capping agent [p. 0028]. Chowdhury teaches examples of capping agents include, for example, acetic anhydride, succinic anhydride, allyl succinic anhydride, propionic anhydride, isobutyric anhydride, isobutenyl succinic anhydride, butenyl succinic anhydride, maleic anhydride, glutaric anhydride, adipic anhydride, salicylic anhydride, phthalic anhydride, acrylic anhydride, methacrylic anhydride, 4-vinylbenzoic anhydride, a corresponding acid chloride thereof, or the like, or a combination thereof. It will be understood that the capping agent further includes diacids capable of forming the corresponding cyclic anhydride under the capping reaction conditions [p. 0028].
Chowdhury discloses the capped poly(arylene ether) copolymer has a number average molecular weight of preferably 500 to 10,000 g/mol, more preferably 500 to 5,000 g/mol, even more preferably 500 to about 2,900 g/mol and an intrinsic viscosity of 0.04 to 1.5 dL/g.
In light of this, it would have been obvious to one having ordinary skill in the art at the time the invention was filed to prepare the poly(arylene ether) of formula (1) as Chowdhury teaches the resin structure as well as suitable capping agents. Furthermore, it would have been obvious to select the claimed number average molecular weight and intrinsic viscosity ranges as the claimed ranges lie inside the ranges taught by Chowdhury. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
Claims 6, 14, 17, and 18 are rejected under 35 U.S.C. 103 as being unpatentable over Irwin et al (US 8058359 B2; herein ‘Irwin’).
Regarding claims 6 and 14; Irwin teaches process for preparing a redistributed poly(phenylene ether), comprising reacting a poly(phenylene ether) in a reactive monomer diluent with a polyhydric phenolic compound in the presence of a redistribution catalyst to form a composition comprising redistributed poly(phenylene ether) in the reactive monomer diluent. [c.17 ll.63-67; c. 18, ll. 1-2]. In example 1, Irwin exemplifies a process wherein:
(1) 10.0 grams of poly(phenylene ether) (SA120 available from SABIC Innovative Plastics in Selkirk N.Y.; having an intrinsic viscosity of 0.12 deciliters per gram, measured at 25 °C., a weight average molecular weight of 7100, and a number average molecular weight of 2700). These materials were dissolved in 14 milliliters of vinyl toluene at 80 °C. To this was added 0.6 gram of bisphenol A and 0.6 gram of benzoyl peroxide (BPO).The resulting composition was heated with stirring for 3.5 hours at a temperature of 90 °C.
(2) Next, 3.5 milliliters of methacrylic anhydride (MAA) and 300 milligrams of dimethylaminopyridine were added. Heating at 90 °C. was continued overnight. Then 1 milliliter water was added to quench excess methacrylic acid anhydride (MAA). After the reaction mixture was cooled to room temperature, it was diluted with 50 milliliters of chloroform to decrease viscosity for a cleaner phase separation, since high viscosity organic phases can lead to stubborn emulsion formation. The solution was transferred to a separatory funnel and washed once with dilute HCl and twice with NaHCO3 solution. After drying with anhydrous K 2CO3, the chloroform and other volatiles were removed under reduced pressure using a rotary evaporator yielding 25 grams of methacrylate capped low intrinsic viscosity poly(phenylene ether) (PPE) in vinyl toluene (about 50% solution). Since the MAA was added in excess, all the hydroxy groups were capped.
Gel permeation chromatographic (GPC) analysis in chloroform of a small sample showed the redistributed polymer to have a number average molecular weight (Mn) of 1923 and a weight average molecular weight (Mw) of 4135, and the intrinsic viscosity of the redistributed poly(phenylene ether) is 0.06 to 0.25 deciliter per gram, measured in chloroform at 25° C [example 1; c. 18, ll. 5-25]. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
Irwin teaches he functionalization of the redistributed poly(phenylene ether) can be accomplished in the reactive monomer diluent, alternatively, the product after redistribution can be isolated by use of an anti-solvent [c. 2, ll. 55; c. 9, ll. 41].
In light of this, it would have been obvious to one having ordinary skill in the art at the time the invention was filed to isolate the product after redistribution or end capping by precipitation, as it is a known purification method in the art and is taught by Irwin as an alternative workup.
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Furthermore, the capped poly(phenylene ether) of Irwin has the general formula:
Wherein the capping groups have a formula where R2, R3, and R4 are each independently hydrogen, C1-C18 hydrocarbyl, C2-C18 hydrocarbyloxycarbonyl, nitrile, formyl, carboxylate, imidate, thiocarboxylate, or the like [c. 10, ll. 20-40].
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Irwin teaches a specific embodiment wherein each occurrence of Q3 and may be a methyl group [c. 12, ll. 1-5]
In light of this, the teachings of Irwin obviously embrace polymer species having the structure of Formula (I) when functionalized with different capping agents. Therefore, it would have been obvious to one having ordinary skill in the art at the time the invention was filed to prepare the polymer of formula (I) as it is taught by Irwin.
Regarding claim 17; Irwin exemplifies the use of bisphenol A: PPE at a ratio of 6:100 [example 1]. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
Regarding claim 18; Irwin exemplifies the use of benzoyl peroxide: PPE at a ratio of 6:100 [example 1]. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
5,880,221
Claims 11, 13, and 15 are rejected under 35 U.S.C. 103 as being unpatentable over Irwin et al (US 8058359 B2; herein ‘Irwin’)in further view of Birsak et al (US 2008/0051522 A1; herein ‘Birsak’).
The disclosure of Irwin is above and is applied here as such.
Irwin exemplifies the preparation of the redistributed poly(phenylene ether) with bisphenol A and benzoyl peroxide in vinyl toluene [step 1, example 1]:
(1) 10.0 grams of poly(phenylene ether) was dissolved in 14 milliliters of vinyl toluene at 80 °C. To this was added 0.6 gram of bisphenol A and 0.6 gram of benzoyl peroxide (BPO).The resulting composition was heated with stirring for 3.5 hours at a temperature of 90 °C.
Irwin teaches other solvents can be used in the redistribution reaction [c. 3, ll. 15-25]. Irwin teaches the functionalization of the redistributed poly(phenylene ether) can be accomplished in the reactive monomer diluent, alternatively, the product after redistribution can be isolated by use of an anti-solvent [c. 2, ll. 55; c. 9, ll. 41]. However, Irwin is silent with a procedure wherein the product after redistribution is isolated with an anti-solvent (precipitation).
Birsak exemplifies the preparation of a redistributed polyphenylene ether resin. To a three-necked flask were added poly(2,6-dimethyl-1,4-phenylene ether) (intrinsic viscosity=0.46 deciliters/gram (dL/g), 90 grams (g)), toluene (260 milliliters (mL)), and bisphenol A (5.4 g). The reaction mixture was heated to 90 °C to form a homogeneous solution. To the heated solution was added benzoyl peroxide (5.4 g) portion-wise. After the addition was complete, the reaction was maintained at 90 °C. for about two hours [0071]. After the reaction mixture was cooled to room temperature, the product was precipitated by combining one volume of the cooled reaction mixture with twice the volume of methanol. The precipitate was filtered and washed with additional methanol [0072].
In light of this, it would have been obvious to one having ordinary skill in the art at the time the invention was filed to precipitate the redistribution product of Irwin with the procedure of Birsak as the reactants and procedure are significantly similar. Furthermore, the temperature of the first reaction is 90 °C in the procedure of Irwin and Birsak, and the procedure of Birsak teaches the product was precipitated at a 1:2 ratio of product in good solvent into poor solvent, therefore it would have been obvious to select these ranges/values.
In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
Claim 19 is rejected under 35 U.S.C. 103 as being unpatentable over Irwin et al (US 8058359 B2; herein ‘Irwin’)in further view of Chowdhury et al (US 2020/0385519 A1; herein ‘Birsak’) and Yeager (US 6,352,782 B2).
The disclosure of Irwin is above and is applied here as such.
Irwin exemplifies the use methacrylic anhydride at a ratio of 6:100 to the poly(phenylene ether) resin [example 1]. Irwin teaches the redistributed poly(phenylene ether) can be functionalized for use in accordance to any suitable method of capping [c. 10, ll. 40-50]. However, Irwin is silent with respect to suitable capping agents beyond methacrylic anhydride.
Chowdhury teaches the capped poly(arylene ether) copolymer is formed by the reaction of an uncapped poly(arylene ether) copolymer, for example an uncapped poly(phenylene ether) copolymer, with a capping agent [p. 0028]. Chowdhury teaches examples of capping agents include, for example, acetic anhydride, succinic anhydride, allyl succinic anhydride, propionic anhydride, isobutyric anhydride, isobutenyl succinic anhydride, butenyl succinic anhydride, maleic anhydride, glutaric anhydride, adipic anhydride, salicylic anhydride, phthalic anhydride, acrylic anhydride, methacrylic anhydride, 4-vinylbenzoic anhydride, a corresponding acid chloride thereof, or the like, or a combination thereof. It will be understood that the capping agent further includes diacids capable of forming the corresponding cyclic anhydride under the capping reaction conditions [p. 0028].
Furthermore, Yeager teaches end capping of poly(phenylene ether) resins with maleic anhydride improves solvent resistance[c. 4, ll. 1-10].
As Irwin teaches the redistributed poly(phenylene ether) can be functionalized according to any suitable method for capping, it would have been obvious to one having ordinary skill in the art at the time the invention was filed to end cap the poly(phenylene ether) of Irwin (at a ratio of 6:100 as taught by Irwin) with maleic anhydride or similar capping species taught by Chowdhury as Yeager teaches capping with maleic anhydride improves solvent resistance. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
Claim 19 is rejected under 35 U.S.C. 103 as being unpatentable over Irwin et al (US 8058359 B2; herein ‘Irwin’) in view of Gallucci et al (US 5,216,089 A).
The disclosure of Irwin is above and is applied here as such.
Irwin exemplifies the use methacrylic anhydride at a ratio of 6:100 to the poly(phenylene ether) resin [example 1]. Irwin teaches the redistributed poly(phenylene ether) can be functionalized for use in accordance to any suitable method of capping [c. 10, ll. 40-50]. However, Irwin is silent with respect to suitable capping agents beyond methacrylic anhydride.
Gallucci teaches a method of improving the flow properties and oxidative stability of a polyphenylene ether resin, the method comprising adding an effective amount of a functionalizing modifiers to the resin [c. 2, ll. 1-10]. Gallucci teaches the polyphenylene ether resins will comprise poly(2,6-dimethyl-1,4-phenylene ether) and copolymers thereof, and the preferred modifiers will comprise dialkyl maleate or fumarate esters, as well as dialkylaryl maleate or fumarate esters, especially dimethyl maleate, dibutyl maleate, diethylhexyl maleate, ditridecyl maleate, dicyclohexyl maleate, dibutyl fumarate, diethylhexyl fumarate, ditridecyl fumarate, dibenzyl fumarate, mixtures of dialkyl fumarates, or mixtures of any of the foregoing [c. 2, ll. 25-40; c. 6, ll. 50-55].
As Irwin teaches the redistributed poly(phenylene ether) can be functionalized according to any suitable method for capping, it would have been obvious to one having ordinary skill in the art at the time the invention was filed to end cap the poly(phenylene ether) of Irwin (at a ratio of 6:100 as taught by Irwin) with dialkyl maleate or fumarate esters as taught by Gallucci, as Gallucci teaches these functionalizing agents improve the flow properties and oxidative stability of poly(phenylene ether) resins. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
Claim 20 is rejected under 35 U.S.C. 103 as being unpatentable over Irwin et al (US 8058359 B2; herein ‘Irwin’) in view of Seo (KR 2015/0035236 A; all citations directed at the English machine translation).
The disclosure of Irwin is above and is applied here as such.
Irwin exemplifies the use of dimethylaminopyridine as a basic catalyst at a ratio of 3:100 relative to poly(phenylene ether) resin [example 1]. Irwin is silent with respect to a general range regarding a suitable amount of basic capping catalyst.
Seo is directed at a modified polyphenylene oxide wherein the redistributed polymer is modified at the ends with aa substituent having low polarity [p. 0031]. The modified phenylene oxide is prepared with an acid anhydride in the presence of a basic catalyst [p. 0148]. Seo teaches dimethylaminopyridine as a preferred basic catalyst and teaches the content of basic catalyst is not particularly limited, but may be 1 to 20 parts by weight based on 100 parts by weight of alcohol-terminated redistributed poly(phenylene oxide) [p. 0150-0151].
As Irwin is silent with respect to a general suitable range for the basic catalyst when preparing the capped poly(phenylene ether) resin, it would have been obvious to one having ordinary skill in the art at the time the invention was filed to perform the end-capping as taught by Irwin with a (1-20):100 ratio of basic catalyst relative to resin as Seo teaches it is a suitable range for the basic catalyst performing terminal modification of poly(phenylene ether) resins. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
Conclusion
Additional relevant documents have been cited on the PTO-892.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to HOLLEY GRACE HESTER whose telephone number is (703)756-5435. The examiner can normally be reached Monday - Friday 9:00AM -5:00PM.
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/HOLLEY GRACE HESTER/ Examiner, Art Unit 1766
/RANDY P GULAKOWSKI/ Supervisory Patent Examiner, Art Unit 1766