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 .
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.
Election/Restrictions
Applicant’s election without traverse of Group I, claims 1 – 21, 24 and 29, in the reply filed on 5/21/26 is acknowledged.
Claim Rejections - 35 USC § 103
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.
Claim(s) 1 – 9 are rejected under 35 U.S.C. 103 as being unpatentable over the NPL titled Comparison of different cyclic organic carbonates in the oxyalkylation of various types of lignin, Kuhnel et al., Reactive and Functional Polymers, 120, 2017, 83 – 91, hereinafter “Kuhnel”.
Kuhnel is directed to the synthesis of biobased polyols from lignin by oxyalkylation with ethylene carbonate (EC), propylene carbonate (PC), butylene carbonate (BC), and glycerol carbonate (GC) (Abstract).
Regarding claims 1 – 5, 7 – 9, 18 and 24, Kuhnel teaches the reaction of lignin with 10 eq of the cyclic organic carbonates EC, PC, BC and GC and 0.1 eq of DBU as a catalyst to form oxyalkylated lignin based polyols. The reaction mixture was allowed to react at 170C with stirring under N2 atmosphere (See 2.1 materials – 2.3.1 Oxyakylation). The lignin, beech wood chips (hardwood) and wheat straw from the organosolve extraction were dried in a vacuum oven at 30C over P2O5 (2.2 Lignin). Butylene carbonate has an alkyl group with 2 carbons. Propylene carbonate satisfies the structural requirements for Formula 1 where N = 1, R1 = CH3 and R’1, Rn+1 and R”n+1 = H (claims 3 and 4). Ethylene carbonate satisfies the structural requires for claim 5
Kuhnel is silent as to the process step of combining wet lignin with the cyclic alkyl carbonate followed by a heating step to remove water to form a dehydrated reaction mixture. It would have been obvious to one of ordinary skill to dry the lignin first before the oxyalkylation reaction or to add the cyclic alkyl carbonate to the wet lignin and then undergo a heating step to dehydrate the lignin prior to addition of the oxyalkylation catalyst to limit the hydrolysis of the cyclic alkyl carbonate and the formation of hydrolysis side reaction products of the cyclic alkyl carbonate. The reduction in water levels would have therefore enhanced the reaction of the cyclic alkyl carbonates with the hydroxyl groups on the lignin molecules and suppressed the formation of side products of the cyclic alkyl carbonate with water.
As to claims 11 – 12, 16 and 17, Kuhnel discloses that the phenol hydroxyl content of the lignin OL1 (Beech) is 5.17 mmol OH / g and the cyclic alkyl carbonate is used at 10 eq relative to the lignin hydroxyl content and 0.1 eq of DBU catalyst (see Table 1 – 2.3.1 Oxyalkylation).
Regarding claims 19 – 20, Kuhnel is silent as to the exact reaction apparatus and synthetic procedures used. However, it would have been obvious to one of ordinary skill to use a sealed reaction vessel and to vent out the carbon dioxide gas which is a byproduct of the reaction to push the reaction to completion.
Allowable Subject Matter
Claims 6, 10, 13 – 15, 21 and 29 are 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.
Prior Art of Record
US 20140275499 A1 to Mikhenevich et al.
US 20110024168 A1 to Okabe et al.
Conclusion
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PAS 7/10/26
/PETER A SALAMON/Primary Examiner, Art Unit 1759
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