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 .
This is in response to the Amendment dated April 27, 2026. The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office Action.
Response to Amendment
Election/Restrictions
This application contains claims 9-10, 16 (species), 11-15 (method) and 17-20 (method) drawn to an invention nonelected without traverse in the reply filed on April 20, 2015.
Claim Objections
Claim 5 has been objected to because of minor informalities.
The objection of claim 5 has been withdrawn in view of Applicant’s amendment.
Claim Rejections - 35 USC § 112
Claims 1, 5 and 8 have been 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.
The rejection of claims 1, 5 and 8 under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, has been withdrawn in view of Applicant’s amendment.
Claim Rejections - 35 USC § 102
Claim(s) 1-3 and 6 have been rejected under 35 U.S.C. 102(a)(1) as being anticipated by Wagenknecht (US Patent No. 4,087,336) as evidenced by Babu et al. (“Simple and Facile Oxidation of Aldehydes to Carboxylic Acids,” Organic Preparations and Procedures International (1994 Feb 1), Vol. 26, No. 1, pp. 123-125).
The rejection of claims 1-3 and 6 under 35 U.S.C. 102(a)(1) as being anticipated by Wagenknecht as evidenced by Babu et al. has been withdrawn in view of Applicant’s remarks.
Claim Rejections - 35 USC § 103
I. Claim(s) 4 and 7-8 have been rejected under 35 U.S.C. 103 as being unpatentable over Wagenknecht (US Patent No. 4,087,336) as evidence by Babu et al. (“Simple and Facile Oxidation of Aldehydes to Carboxylic Acids,” Organic Preparations and Procedures International (1994 Feb 1), Vol. 26, No. 1, pp. 123-125) as applied to claims 1-3 and 6 above, and further in view of Abitelli et al. (“Probing for a Leaving Group Effect on the Generation and Reactivity of Phenyl Cations,” The Journal of Organic Chemistry (2012 Apr 6), Vol. 77, No. 7, pp. 3501-3507) and Waldvogel et al. (“Electrochemical Arylation Reaction,” Chemical Reviews (2018 Jul 2), Vol. 118, No. 14, pp. 6706-6765).
The rejection of claims 4 and 7-8 have been rejected under 35 U.S.C. 103 as being
unpatentable over Wagenknecht as evidence by Babu et al. as applied to claims 1-3 and 6 above, and further in view of Abitelli et al. and Waldvogel et al. has been withdrawn in view of Applicant’s remarks.
II. Claim(s) 5 has been rejected under 35 U.S.C. 103 as being unpatentable over Wagenknecht (US Patent No. 4,087,336) as applied to claims 1-3 and 6 above, and further in view of Babu et al. (“Simple and Facile Oxidation of Aldehydes to Carboxylic Acids,” Organic Preparations and Procedures International (1994 Feb 1), Vol. 26, No. 1, pp. 123-125).
The rejection of claim 5 under 35 U.S.C. 103 as being unpatentable over Wagenknecht as applied to claims 1-3 and 6 above, and further in view of Babu et al. has been withdrawn in view of Applicant’s remarks.
Continued Response
Claim Rejections - 35 USC § 102
I. Claim(s) 1-3 and 6 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Amarasekara et al. (“Vanillin Based Polymers: I. An Electrochemical Route to Polyvanillin,” Green Chemistry (2012), Vol. 14, No. 9, pp. 2395-2397).
Regarding claim 1, Amarasekara teaches a method of synthesizing a functionalized biphenol compound (= preparation of polyvanillin (3)) [page 2395, right column, lines 23-24], comprising the steps of:
• providing a solution (= 1 M aq. NaOH in water) [page 2396, Fig. 1] comprising a phenol
compound functionalized with at least one substituent which is -COOH or a non-halogen substituent that is convertible to a -COOH substituent (= divanillin (2):
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)
[page 2395, Fig. 1] in a solvent (= water) [page 2396, Fig. 1], and
• subjecting said functionalized phenol compound to an electrochemical coupling reaction whereby two functionalized phenol molecules couple together thereby forming a functionalized biphenol compound having a C-C bond between two phenol rings (= preparation of polyvanillin (3) by electrochemical polymerization of the vanillin dimer, divanillin (2) [page 2395, right column, lines 23-25]; and Fig. 1:
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).
Regarding claim 2, Amarasekara teaches wherein said non-halogen substituent that is convertible to a -COOH substituent is -CN or C(=O)R1 where R1 is selected from H, an alkyl, and an -O-alkyl (= divanillin (2): OCH where R1 is H) [page 2395, Fig. 1].
Regarding claim 3, Amarasekara teaches wherein said electrochemical coupling reaction
is a reductive coupling reaction (= preparation of polyvanillin (3) by electrochemical
polymerization of the vanillin dimer, divanillin (2) [page 2395, right column, lines 23-25]; and Fig. 1:
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).
Regarding claim 6, Amarasekara teaches wherein said solvent is selected from water, one or more alkyl alcohols, and a mixture of water and one or more alkyl alcohols (= water) [page 2396, Fig. 1].
II. Claim(s) 1 and 2 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Yankin et al. (“Aryl‐Aryl Coupling of Salicylic Aldehydes Through Oxidative CH‐Activation in Nickel Salen Derivatives,” ChemistrySelect (2019 Aug 14), Vol. 4, No. 30, pp. 8886-8890).
Regarding claim 1, Yankin teaches a method of synthesizing a functionalized biphenol compound (= the electrochemical aryl-aryl coupling of salicylic aldehydes) [page 8886, abstract], comprising the steps of:
• providing a solution comprising a phenol compound functionalized with at least one substituent which is -COOH or a non-halogen substituent that is convertible to a -COOH substituent (= 3-methyl-2-hydroxybenzaldehyde 1a) [page 8887, left column, line 12] in a solvent (= ethylenediamine) [page 8887, right column, line 14], and
• subjecting said functionalized phenol compound (= the one-pot procedure for the
transformation of 1a to 4a was also tested) [page 8887, right column, lines 12-13] to an
electrochemical coupling reaction (= the electrochemical aryl-aryl coupling of salicylic aldehydes) [page 8886, abstract] whereby two functionalized phenol molecules couple together thereby forming a functionalized biphenol compound having a C-C bond between two phenol rings (= for the transformation of 3-methyl-2-hydroxybenzaldehyde 1a to 4,4’-dihydroxy-3,3’-diformyl-5,5’-dimethylbiphenyl 4a) [page 8887, left column, lines 7-9].
Regarding claim 2, Yankin teaches wherein said non-halogen substituent that is convertible to a -COOH substituent is -CN or C(=O)R1 where R1 is selected from H, an alkyl, and an -O-alkyl (= 3-methyl-2-hydroxybenzaldehyde 1a:
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where R1 = H) [page 8887, line 7-8].
III. Claim(s) 1 and 6 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by DE 102013211744 (‘744).
Regarding claim 1, DE ‘744 teaches a method of synthesizing a functionalized biphenol compound (= electrochemical process for the production of symmetrical biphenols) [ρ [0041]] comprising the steps of:
• providing a solution (= the reaction solution) [ρ [0060]] comprising a phenol compound functionalized with at least one substituent which is -COOH or a non-halogen substituent that is convertible to a -COOH substituent (= addition of a phenol of general
formula I to a reaction vessel (ρ [0041]); and
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where in one variant of the procedure, R1 to R4 are each independently selected from: H, -(C1-C4)-alkyl, -Cl (ρ [0045]; and ρ [0013] of the document)) in a solvent (= adding water to the reaction vessel) [ρ [0055]], and
• subjecting said functionalized phenol compound to an electrochemical coupling reaction whereby two functionalized phenol molecules couple together thereby forming a functionalized biphenol compound having a C-C bond between two phenol rings (= application of voltage to the two electrodes, so that two molecules I are electrochemically coupled to form
a biphenol of the general formula II (ρ [0042]); and
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where the residues R1to R4 correspond to the definition from process step a) [ρ [0042]; and ρ [0013] of the document]).
Regarding claim 6, DE ‘744 teaches wherein said solvent is selected from water, one or
more alkyl alcohols, and a mixture of water and one or more alkyl alcohols (= adding water to
the reaction vessel) [ρ [0055]].
Claim Rejections - 35 USC § 103
I. Claim(s) 4 and 7-8 is/are rejected under 35 U.S.C. 103 as being unpatentable over Amarasekara et al. (“Vanillin Based Polymers: I. An Electrochemical Route to Polyvanillin,” Green Chemistry (2012), Vol. 14, No. 9, pp. 2395-2397) as applied to claims 1-3 and 6 above, and further in view of Waldvogel et al. (“Electrochemical Arylation Reaction,” Chemical Reviews (2018 Jul 2), Vol. 118, No. 14, pp. 6706-6765).
Regarding claim 4, Amarasekara teaches the method of at least claims 1-3 and 6 as
applied above. The reference does not explicitly teach wherein said functionalized phenol compound is further functionalized with a leaving group, which leaving group leaves the functionalized phenol compound to form a coupling site, such that a C-C bond is formed between two coupling sites.
Waldvogel teaches products of electrochemical arylation reactions:
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(page 6708, Scheme 1; and page 6727, Scheme 48: electroreductive coupling).
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to have modified the functionalized phenol compound described by Amarasekara with wherein said functionalized phenol compound is further functionalized with a leaving group, which leaving group leaves the functionalized phenol
compound to form a coupling site, such that a C-C bond is formed between two coupling sites. The person with ordinary skill in the art would have been motivated to make this modification because phenyl cations would have been generated by the cleavage of a C-X bond which leaves a site for electroreductive coupling as taught by Waldvogel on page 6708, Scheme 1; and page 6727, Scheme 48: electroreductive coupling.
MPEP § 2143(I)(A) states that “combining prior art elements according to known methods to yield predictable results” may be obvious. The claimed elements were known in the
prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination would yield nothing more than predictable results. Furthermore, MPEP § 2144.07 states that “the selection of a known material based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 US 327, 65 USPQ 297 (1945).”
Regarding claim 7, Waldvogel teaches wherein said leaving group is a halogen (= X = Cl,
Br) [page 6727, Scheme 48].
Regarding claim 8, Amarasekara teaches the method of at least claims 1-3 and 6 as
applied above. The reference does not explicitly teach wherein said functionalized phenol compound is 5-bromosalicylaldehyde.
Amarasekara teaches divanillin (2) [page 2395, Fig. 1].
It would have been obvious to one having ordinary skill in the art before the effective
filing date of the claimed invention to have modified the functionalized phenol described by
Amarasekara with wherein said functionalized phenol is 5-bromosalicylaldehyde. The person with ordinary skill in the art would have been motivated to make this modification because vanillin and 5-bromosalicylaldehyde are both benzaldehydes where 5-bromosalicylaldehyde would have been suitable for electrochemical reduction polymerization because the substitution of one benzaldehyde for another is likely to be obvious when it does no more than yield predictable results.
II. Claim(s) 5 is/are rejected under 35 U.S.C. 103 as being unpatentable over Amarasekara et al. (“Vanillin Based Polymers: I. An Electrochemical Route to Polyvanillin,” Green Chemistry (2012), Vol. 14, No. 9, pp. 2395-2397) as applied to claims 1-3 and 6 above, and further in view of Babu et al. (“Simple and Facile Oxidation of Aldehydes to Carboxylic Acids,” Organic Preparations and Procedures International (1994 Feb 1), Vol. 26, No. 1, pp. 123-125).
Regarding claim 5, Amarasekara teaches the method of at least claims 1-3 and 6 as
applied above. The reference does not explicitly teach wherein a symmetrical functionalized biphenol compound that is a product of the electrochemical reductive coupling reaction is
subjected to an oxidation step or a hydrolysis step to convert the non-halogen substituent to -C(=O)OH to produce a biphenol dicarboxylate compound.
Amarasekara teaches divanillin (2) [page 2395, Fig. 1].
Babu teaches the oxidation of 3,4-(MeO)(OH)C6H3CHO (= vanillin) by sodium chlorite (page 124, Table: Aldehydes 4 and 5) to the corresponding acids (page 123, lines 1-3).
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to have modified the symmetrical functionalized biphenol compound as described by Amarasekara with wherein a symmetrical functionalized biphenol compound that is a product of the electrochemical reductive coupling reaction is subjected to an oxidation step or a hydrolysis step to convert the non-halogen substituent to -C(=O)OH to
produce a biphenol dicarboxylate compound. The person with ordinary skill in the art would have been motivated to make this modification because oxidizing 3,4-(MeO)(OH)C6H3CHO (= vanillin) by sodium chlorite would have been a simple and facile way to give corresponding carboxylic acids from aldehydes.
MPEP § 2143(I)(A) states that “combining prior art elements according to known methods to yield predictable results” may be obvious. The claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination would yield nothing
more than predictable results.
Citations
WO 2023/278766 is cited to teach the electrochemical reductive homo-coupling and/or electrochemical reductive cross-coupling of substituted phenol derivatives to form the corresponding substituted biphenyls (ρ [0003]; and Fig. 1).
Any inquiry concerning this communication or earlier communications from the examiner should be directed to EDNA WONG whose telephone number is (571) 272-1349. The examiner can normally be reached Monday-Friday, 7:00 AM- 3:30 PM.
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/EDNA WONG/Primary Examiner, Art Unit 1795
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