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 14-16 and 22-39 are pending.
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 14-16, 22-25, 27-30, and 39 are rejected under 35 U.S.C. 103 as being unpatentable over Synthesis and characterization of silica-supported Pd nanoparticles and its application in the Heck reaction by Ghiaci et al. (Ghiaci).
In regard to claim 14, Ghiaci teaches a method of functionalizing a polymer comprising alkene groups (pg. 888, 2. Experimental, silica, terminal alkenes). Ghiaci teaches reacting said polymer with a first reactant comprising a thiol group and a linking group (pg. 888, 2. Experimental, 1,2-ethanedithiol; pg. 888, 2. Results and discussion, amino-functionalized silica). Ghiaci teaches a first reactant thiol group reacts with a polymer alkene group in a thiol-ene reaction to form a thioether linkage between said polymer and said linking group (pg. 888, 2. Experimental, 1,2-ethanedithiol). Ghiaci teaches reacting the product of step a with a second reactant comprising an aryl or heteroaryl group (pg. 888, 2. Experimental, cyanuric chloride). Ghiaci teaches said aryl group or heteroaryl group is substituted or unsubstituted to bind the second reactant to the linking group (pg. 888, 2. Experimental, cyanuric chloride). Ghiaci teaches reacting the product of step b with a third reactant having a functional moiety (pg. 888, 2. Experimental, sodium acetate). Ghiaci teaches wherein said third reactant binds to said second reactant to link said functional moiety thereto thereby functionalizing said polymer with said functional moiety to create a functionalized polymer (pg. 888, 2. Experimental). The order of performing process steps is prima facie obvious in the absence of new or unexpected results; the selection of any order of mixing ingredients is prima facie obvious. Ex parte Rubin, 128 USPQ 440 (Bd. App. 1959). While Ghiaci does not state specific ways in which the components react, it would be obvious to one of ordinary skill in the art that the components will react in predictable ways with specific attachments.
In regard to claim 15, Ghiaci teaches said functional moiety linked to bound second reactant by the reaction of step c comprising a thiol group, a thio group, or a combination of both (pg. 888, 2. Experimental, SiO2-pr-NH-cyanuric-SH).
In regard to claim 16, Ghiaci teaches said third reactant is selected from a sulfide salt and a polythiolated alkane (pg. 888, 2. Experimental, SiO2-pr-NH-cyanuric-SH).
In regard to claim 22, Ghiaci teaches said second reactant comprises a heteroaryl group (pg. 888, 2. Experimental, cyanuric chloride).
In regard to claim 23, Ghiaci teaches said heteroaryl group comprises a substituted triazine group (pg. 888, 2. Experimental, cyanuric chloride).
In regard to claim 24, Ghiaci teaches said first reactant is a thiol compound of the formula HS-C1-C6alkyl-R wherein the moiety R comprises a linking group selected from saturated and unsaturated alkyl, aryl, heteroaryl, halide, -OH, -NH2, -NHR’, -NR’2, -COOH, -NO2, -COH, -CO(NH2), -CO(NR’H), -CO(NR’2), -CN, -N(OH)NO, where R’ is independently C1-C6alkyl (pg. 888, 2. Experimental, 1,2-ethanedithiol).
In regard to claim 25, Ghiaci teaches the first reactant is HSC2H4NH2 (pg. 888, 2. Experimental, 1,2-ethanedithiol; pg. 888, 2. Results and discussion, amino-functionalized silica).
In regard to claim 27, Ghiaci teaches said second reactant comprises an aryl or heteroaryl group that is selected from monocyclic, bicyclic, or polycyclic (pg. 888, 2. Experimental, cyanuric chloride).
In regard to claim 28, Ghiaci teaches the second reactant is substituted with at least one halide substituent (pg. 888, 2. Experimental, cyanuric chloride).
In regard to claim 29, Ghiaci teaches said second reactant comprises a heteroaryl group that is a substituted triazine (pg. 888, 2. Experimental, cyanuric chloride).
In regard to claim 30, Ghiaci teaches said second reactant is cyanuric chloride (pg. 888, 2. Experimental, cyanuric chloride).
In regard to claim 39, Ghiaci teaches a functionalized polymer made by the process of claim 14 (pg. 888, 2. Experimental).
Claims 34-37 are rejected under 35 U.S.C. 103 as being unpatentable over Synthesis and characterization of silica-supported Pd nanoparticles and its application in the Heck reaction by Ghiaci et al. (Ghiaci), as noted above, in view of WO2017205166 by Guliashvili et al. (Guliashvili).
In regard to claims 34-37, Ghiaci teaches all the limitations as noted above. Ghiaci does not teach the polymer is a macroreticular polymer with an average pore size in the range of 20-200 Å, with a pore volume of at least 0.65 cm3/g and a particle size distribution D90 ranging from about 50-150 microns.
Guliashvili teaches the polymer is a macroreticular polymer ([0018]-[0019], [0069], [0126] reading on claim 34) has an average pore size in the range of 20-200 Å ([0018]-[0019], reading on claim 35) with a pore volume of at least 0.65 cm3/g ([0018]-[0019], reading on claim 36) and a particle size distribution ([0121], [0126], Table XVII, reading on claim 37).
It would have been obvious to one of ordinary skill in the art at the time of 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. In re Malagari, 182 USPQ 549.
Guliashvili does not explicitly teach a particle size distribution D90 ranging from about 50-150 microns ([0121], [0126], Table XVII), as the polymer size and efficiency of operation are variables that can be modified, among others, by adjusting said particle size distribution, the precise particle size distribution would have been considered a result effective variable by one having ordinary skill in the art at the time the invention was made. As such, without showing unexpected results, the claimed particle size distribution cannot be considered critical. Accordingly, one of ordinary skill in the art at the time the invention was made would have optimized, by routine experimentation, the particle size distribution in the method of Ghiaci to obtain the desired balance between the construction cost and the operation efficiency (In re Boesch, 617 F.2d. 272, 205 USPQ 215 (CCPA 1980)), since it has been held that where the general conditions of the claim are disclosed in the prior art, discovering the optimum or workable ranges involves only routine skill in the art. (In re Aller, 105 USPQ 223).
Response to Arguments
Applicant's arguments filed 9/11/2025 have been fully considered but they are not persuasive.
The 112b and 112a rejections of claim 25 are removed in light of the arguments.
In regard to the Applicant’s argument Giaci does not have alkene groups; Ghiaci does not teach terminal alkenes; the Examiner does not find this persuasive.
In response to applicant's argument that the references fail to show certain features of the invention, it is noted that the features upon which applicant relies (i.e., terminal alkene) 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).
As noted above: Ghiaci teaches a method of functionalizing a polymer comprising alkene groups (pg. 888, 2. Experimental, silica, terminal alkenes).
In regard to the Applicant’s argument Ghiaci does not teach a first reactant with thiol groups; the 1,2-ethanedithiol does not react with any polymer alkene group nor is there a polymer alkene group present for a thiol group to react with in a thio-ene reaction; the thiol group of Ghiaci reacts with a chloride ion of the cyanuric chloride group; the Examiner does not find this persuasive.
As noted above: Ghiaci teaches reacting said polymer with a first reactant comprising a thiol group and a linking group (pg. 888, 2. Experimental, 1,2-ethanedithiol; pg. 888, 2. Results and discussion, amino-functionalized silica). Ghiaci teaches a first reactant thiol group reacts with a polymer alkene group in a thiol-ene reaction to form a thioether linkage between said polymer and said linking group (pg. 888, 2. Experimental, 1,2-ethanedithiol).
The applicant has not provided any evidence as to why the thiol will only react with the chloride ion.
The 1,2-ethanedithiol is considered the polymer alkene.
In regard to the Applicant’s argument Ghiaci does not teach a thiol between the silica and cyanuric chloride therefore the cyanuric chloride is not reacting with anything that could be described as the reaction product of step a in the claim; the Examiner does not find this persuasive.
Ghiaci teaches all the products are reacting with one another.
In regard to the Applicant’s argument regarding the order of process steps; there are unexpected results which result in superior properties; the Examiner does not find this persuasive.
The Applicant has not submitted any evidence of unexpected results.
In regard to the Applicant’s argument Guliashvii teaches away from the claimed average pore size; the Examiner does not find this persuasive.
The overlapping range of Guliashvii reads on the claimed range. It would have been obvious to one of ordinary skill in the art at the time of 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. In re Malagari, 182 USPQ 549.
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.
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/KARA M PEO/Primary Examiner, Art Unit 1777