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 August 20, 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
Claim Rejections - 35 USC § 102
I. Claim(s) 1-3 and 6 have been 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).
The rejection of claims 1-3 and 6 under 35 U.S.C. 102(a)(1) as being anticipated by Amarasekara et al. has been withdrawn in view of Applicant’s amendment.
II. Claim(s) 1 and 2 have been 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).
The rejection of claims 1 and 2 under 35 U.S.C. 102(a)(1) as being anticipated by Yankin et al. has been withdrawn in view of Applicant’s amendment.
III. Claim(s) 1 and 6 have been rejected under 35 U.S.C. 102(a)(1) as being anticipated by DE
102013211744 (‘744).
The rejection of claims 1 and 6 under 35 U.S.C. 102(a)(1) as being anticipated by DE 102013211744 (‘744) has been withdrawn in view of Applicant’s amendment.
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 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).
The rejection of claims 4 and 7-8 under 35 U.S.C. 103 as being unpatentable over Amarasekara et al. as applied to claims 1-3 and 6 above, and further in view of Waldvogel et al. has been withdrawn in view of Applicant’s amendment.
II. Claim(s) 5 has been 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).
The rejection of claim 5 under 35 U.S.C. 103 as being unpatentable over Amarasekara et al. 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 amendment.
Continued Response
Claim Rejections - 35 USC § 102
Claim(s) 22 and 27 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 22, Yankin teaches a method of synthesizing a functionalized biphenol compound (= the one-pot procedure for the transformation of 1a to 4a) [page 8887, right column, line 12], the method comprising:
• providing a solution comprising a functionalized phenol compound (= the electrolyte solution from 1a) [page 8887, right column, line 14] and a solvent (= ethylenediamine) [page 8887, right column, line 14], wherein the functionalized phenol compound comprises at least one substituent which is -COOH, -CN, or C(=O)R1 wherein R1 is H, an alkyl group, or an -O-alkyl group (= 3-methyl-2-hydroxybenzaldehyde 1a) [page 8887, left column, line 10-11]; and
• subjecting the functionalized phenol compound to an electrochemical coupling reaction (= 2a was prepared directly in the electrolyte solution from 1a, ethylenediamine and nickel perchlorate and then subjected to oligomerization in the same reaction vessel) [page 8887, left column, lines 12-16] whereby two functionalized phenol molecules couple together
thereby forming the functionalized biphenol compound having a C-C bond between two phenol rings (= transformation of 3-methyl-2-hydroxybenzaldehyde 1a to 4,4’-dihydroxy-3,3’-diformyl-5,5’-dimethylbiphenyl 4a) [page 8887, left column, lines 10-12];
wherein the solvent is water (= the electropolymerization of 2a with different water content in the supporting electrolyte) [page 8887, right column, line 31, to page 8888, left column, line 1] or a mixture of water and one or more alkyl alcohols.
Regarding claim 27, Yankin does not explicitly teach wherein the functionalized biphenol compound is
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wherein R is COOH or C(=O)H.
The subject matter would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to because:
(i) The functionalized biphenol compound is the product produced by the process. A process yielding an unobvious product may nonetheless be obvious where Applicant claims a
process in terms of function, property or characteristic and the process of the prior art is the same or similar as that of the claim but the function, property or characteristic is not explicitly disclosed by the reference (MPEP § 2116.01).
(ii) Yankin teaches the electrolysis process conditions that can be used in order to make the functionalized biphenol compound as presently claimed. Similar processes can reasonably
be expected to yield products which inherently have the same properties. In re Spada 911 F.2d 705, 15 USPQ 2d 1655 (CAFC 1990); In re DeBlauwe 736 F.2d 699, 222 USPQ 191 (CAFC 1984); In re Wiegand 182 F.2d 633, 86 USPQ 155 (CCPA 1950).
Claim Rejections - 35 USC § 103
Claim(s) 26 is/are rejected under 35 U.S.C. 103 as being unpatentable over 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) as applied to claims 22 and 27 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 26, Yankin teaches the method of at least claims 22 and 27 as applied above. Yankin also teaches wherein the at least one substituent is -CN or C(=O)R1 (= the starting salicylic aldehyde 1 (Figure 1))1 [page 8887, left column, lines 2-3].
Yankin does not explicitly teach wherein the method further comprises subjecting the functionalized biphenol compound to oxidation or hydrolysis to convert the at least one substituent to -COOH to produce a biphenol dicarboxylate compound.
Babu teaches the oxidation of 4-HOC6H4CHO2 by sodium chlorite (page 124, Table: Aldehyde 4) 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 method as described by Yankin with wherein the method further comprises subjecting the functionalized biphenol compound to oxidation or hydrolysis to convert the at least one substituent to -COOH to produce a biphenol
dicarboxylate compound. The person with ordinary skill in the art would have been motivated to make this modification because oxidizing 4-HOC6H4CHO (4-hydroxybenzaldehyde) 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.
Allowable Subject Matter
The following is a statement of reasons for the indication of allowable subject matter:
Claims 1-8 and 21 define over the prior art of record because the prior art does not contain any language that teaches or suggests a method of synthesizing a functionalized biphenol compound comprising the steps of providing and subjecting as presently claimed, esp., subjecting the functionalized phenol compound to an electrochemical coupling reaction whereby the leaving group leaves the functionalized phenol compound to form a coupling site.
Claims 23-25 define over the prior art of record because the prior art does not contain any language that teaches or suggests the method of claim 22, wherein the functionalized phenol compound is further functionalized with a leaving group, and wherein during the electrochemical coupling reaction the leaving group leaves the functionalized phenol compound to form a coupling site that forms the C-C bond between the two phenol rings. Therefore, a person skilled in the art would not have been motivated to adopt the above conditions, and a prima facie case
of obviousness cannot be established.
Yankin teaches that the synthesis of a series of 4,4’-dihydroxy-3,3’-diformylbiphenyls from substituted salicylic aldehydes via the electrooxidative coupling of bis(salicylidenimino)nickel(II) complexes (page 8886, right column, lines 10-13).
Claims 23-25 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.
Response to Arguments
Applicant’s arguments filed August 20, 2026 have been fully considered but they are not persuasive.
Applicant states that Yankin teaches a method that includes an NiSalen complex intermediate, wherein Yankin advises that “traces of water have severe impact on the electroactivity of metal-Salen based polymers.”
In response, Yankin performed the comparative study for the electropolymerization of 2a
with different water content in the supporting electrolyte (page 8887, right column, line 29, to page 8888, left column, line 1). The comparison of the cyclic voltammograms obtained on
ITO from the dry and wet experiments indicates an ability of 2a to form the polymeric product even in the presence of a large amount of water (Figure 3) [page 8888, left column, lines 7-10].
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.
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.
Examiner interviews are available via telephone, in-person, and video conferencing
using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Luan Van can be reached at (571) 272-8521. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/EDNA WONG/Primary Examiner, Art Unit 1795
1 Structure 1b where R1 to R5 = H is 2-hydroxybenzaldehyde.
2 4-HOC6H4CHO = 4-hydroxybenzaldehyde.
