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 .
Election/Restrictions
Applicant’s election without traverse of Group I, species (i), claims 1-8, in the reply filed on November 24, 2025 is acknowledged.
The requirement is still deemed proper and is therefore made FINAL.
Accordingly, claims 9-10 (species) and 11-20 (methods) are withdrawn from consideration as being directed to a non-elected invention.
Claim Objections
Claim 5 is objected to because of the following informalities:
Claim 5
line 1, please delete the phrase “R1 is not -OH, and”. Claim 2, line 2, already recites “where R1 is selected from H, an alkyl, and an -O-alkyl”, which clearly does not include -OH, and thus, this limitation does not add anything to the claim and is just pointing out the obvious.
line 2, please amend the word “step” to the word -- reaction --. See claim 3, line 2.
This is an instance where the article should be changed to ensure proper antecedent basis for the claim terminology.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
Claims 1, 5 and 8 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.
Claim 1
line 5, “said functionalized phenol molecules” lack antecedent basis.
Antecedent basis must be laid for each recited element in a claim, typically, by introducing each element with the indefinite article (“a” or “an”). See Slimfold Mfg. Co. v. Kincaid Properties, Inc., 626 F. Supp 493, 495 (N.D. Ga. 1985), aff'd, 810 F.2d 1113 (Fed. Cir.
1987) (citing P. Rosenberg, 2 Patent Law Fundamentals § 14.06 (2d. Ed. 1984)). Subsequent mention of an element is to be modified by the definite article “the”, “said” or “the said,” thereby making the latter mention(s) of the element unequivocally referable to its earlier recitation.
Claim 5
line 1-2, “the symmetrical functionalized biphenol compound” lacks antecedent basis.
Antecedent basis must be laid for each recited element in a claim, typically, by
introducing each element with the indefinite article (“a” or “an”). See Slimfold Mfg. Co. v.
Kincaid Properties, Inc., 626 F. Supp 493, 495 (N.D. Ga. 1985), aff'd, 810 F.2d 1113 (Fed. Cir.
1987) (citing P. Rosenberg, 2 Patent Law Fundamentals § 14.06 (2d. Ed. 1984)). Subsequent mention of an element is to be modified by the definite article “the”, “said” or “the said,”
thereby making the latter mention(s) of the element unequivocally referable to its earlier recitation.
line 2, “the product” lacks antecedent basis.
Antecedent basis must be laid for each recited element in a claim, typically, by introducing each element with the indefinite article (“a” or “an”). See Slimfold Mfg. Co. v. Kincaid Properties, Inc., 626 F. Supp 493, 495 (N.D. Ga. 1985), aff'd, 810 F.2d 1113 (Fed. Cir.
1987) (citing P. Rosenberg, 2 Patent Law Fundamentals § 14.06 (2d. Ed. 1984)). Subsequent mention of an element is to be modified by the definite article “the”, “said” or “the said,” thereby making the latter mention(s) of the element unequivocally referable to its earlier recitation.
Claim 8
line 1, “said functionalized phenol” lacks antecedent basis.
Antecedent basis must be laid for each recited element in a claim, typically, by introducing each element with the indefinite article (“a” or “an”). See Slimfold Mfg. Co. v. Kincaid Properties, Inc., 626 F. Supp 493, 495 (N.D. Ga. 1985), aff'd, 810 F.2d 1113 (Fed. Cir.
1987) (citing P. Rosenberg, 2 Patent Law Fundamentals § 14.06 (2d. Ed. 1984)). Subsequent
mention of an element is to be modified by the definite article “the”, “said” or “the said,” thereby making the latter mention(s) of the element unequivocally referable to its earlier recitation.
line 1, recites “said functionalized phenol”.
It is unclear from the claim language what the relationship is between said functionalized phenol and the phenol compound functionalized with at least one substituent which is -COOH or a non-halogen substituent that is convertible to a -COOH substituent in claim 1, lines 2-3, and the functionalized phenol molecules recited in claim 1, line 5.
Is “said functionalized phenol” further limiting one of them, i.e., the compound or the molecules?
Claim Rejections - 35 USC § 102
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 the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale,
or otherwise available to the public before the effective filing date of the claimed invention.
Claim(s) 1-3 and 6 is/are 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).
Regarding claim 1, Wagenknecht teaches a method of synthesizing a functionalized biphenol compound comprising the steps of:
• providing a solution (= an aqueous alkaline electrolysis medium) [col. 3, lines 18-19] comprising a phenol compound functionalized with at least one substituent which is -COOH or a non-halogen substituent (= the hydroxybenzaldehydes suitable for use are represented by the formula1:
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wherein X represents alkyl of 1 to 6 carbon atoms; Y represents alkoxy containing an alkyl of 1 to 6 carbon atoms; Z represents any non-interfering substituent, excluding alkyl and alkoxy; and a, b, and c each independently represent an integer from 0 (zero) to 4, inclusive, with the proviso that the sum of a, b, and c does not exceed 4) [col. 1, line 67 to col. 2, line 16] in a
solvent (= aqueous solvent) [col. 1, line 66], and
• subjecting said functionalized phenol compound to an electrochemical coupling
reaction whereby two of said functionalized phenol molecules couple together thereby forming a functionalized biphenol compound having a C-C bond between two phenol rings (= electrolytic reductive coupling of hydroxybenzaldehydes in an undivided cell leads to 1,2-bis(hydroxyphenyl)-ethane-1,2-diols (col. 1, lines 60-62); and the reaction:
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(col. 3, lines 1-17)).
Wagenknecht does not explicitly teach wherein the non-halogen substituent is convertible to a -COOH substituent. However,
Wagenknecht teaches that representative of hydroxybenzaldehydes suitable for use in the process includes 4-hydroxybenzaldehyde (p-hydroxybenzaldehyde) [col. 2, lines 27-28] and 4-hydroxy-3-methoxybenzaldehyde (vanillin) [col. 2, lines 39-40].
Babu teaches the oxidation of 4-HOC6H4CHO (= 4-hydroxybenzaldehyde) and 3,4--
(MeO)(OH)C6H3CHO (= vanillin) by sodium chlorite (page 124, Table: Aldehydes 4 and 5) to their corresponding acids (page 123, lines 1-3).
Thus, the non-halogen substituent, i.e., -CHO, in the hydroxybenzaldehydes disclosed by
Wagenknecht is convertible to their corresponding acids, i.e., -COOH2, when oxidized by sodium chlorite, as evidenced by Babu.
Regarding claim 2, Wagenknecht 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 (= C(=O)R1 where R1 is H) [col. 3, line 5:
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].
Regarding claim 3, Wagenknecht teaches wherein said electrochemical coupling reaction is a reductive coupling reaction (= electrolytic reductive coupling of hydroxybenzaldehydes) [col. 1, lines 60-61].
Regarding claim 6, Wagenknecht teaches wherein said solvent is selected from water (= wherein the aqueous solvent is water) [col. 10, claim 7], one or more alkyl alcohols, and a mixture of water and one or more alkyl alcohols (= alcohols such as methanol and ethanol can also be added to the electrolysis medium up to about 50 percent by weight) [col. 3, lines 23-25].
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.
I. Claim(s) 4 and 7-8 is/are 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).
Wagenknecht and Babu are as applied above and incorporated herein.
Regarding claim 4, the method of Wagenknecht differs from the instant invention because Wagenknecht does not disclose 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.
Abitelli teaches that phenyl cations are smoothly generated by the photoheterolytic
cleavage of an Ar−LG bond (LG = leaving group) [page 3501, abstract and Scheme 1:
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].
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 Wagenknecht 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 because phenyl cations are smoothly generated by the cleavage of an Ar−LG bond (LG = leaving
group) which leaves a site for 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 “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, the method of Wagenknecht differs from the instant invention because Wagenknecht does not disclose wherein said functionalized phenol is 5- bromosalicylaldehyde.
Wagenknecht teaches salicylaldehyde (= representative of hydroxybenzaldehydes suitable for use in the process are 2-hydroxybenzaldehyde (o-hydroxybenzaldehyde, 3-hydroxybenzaldehyde (m-hydroxybenzaldehyde)) [col. 2, lines 24-27].
Abitelli teaches wherein said leaving group is a halogen (= Br) [page 3502, Chart 1].
Waldvogel teaches wherein said leaving group is a halogen (= X= Cl, Br) [page 6727, Scheme 48].
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
Wagenknecht with wherein said functionalized phenol is 5-bromosalicylaldehyde because attaching Br to the salicylaldehyde of Wagenknecht as a leaving group can smoothly generate phenyl cations by the cleavage of the Ar−LG bond (LG = leaving group) which leaves a site for electroreductive coupling.
MPEP § 2144.09 states that “[a] prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.”
II. Claim(s) 5 is/are 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).
Wagenknecht is as applied above and incorporated herein.
Regarding claim 5, Wagenknecht teaches wherein R1 is not -OH (= CHO wherein R1 is H) [col. 3, line 5].
The method of Wagenknecht differs from the instant invention because Wagenknecht does not disclose where the symmetrical functionalized biphenol compound that is the product of the electrochemical reductive coupling step 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.
Wagenknecht teaches that representative of hydroxybenzaldehydes suitable for use in
the process includes 4-hydroxybenzaldehyde (p-hydroxybenzaldehyde) [col. 2, lines 27-28] and 4-hydroxy-3-methoxybenzaldehyde (vanillin) [col. 2, lines 39-40].
Babu teaches the oxidation of 4-HOC6H4CHO (= 4-hydroxybenzaldehyde) and 3,4--(MeO)(OH)C6H3CHO (= vanillin) by sodium chlorite (page 124, Table: Aldehydes 4 and 5) to their 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 Wagenknecht with where the symmetrical functionalized biphenol compound that is the product of the electrochemical reductive coupling step 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 because oxidizing 4-HOC6H4CHO (= 4-hydroxybenzaldehyde) and 3,4--(MeO)(OH)C6H3CHO (= vanillin) by sodium chlorite is 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
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Kunkel et al. (“Electrochemical Synthesis of Biobased Polymers and Polymer Building Blocks from Vanillin,” RSC Advances (2021), Vol. 11, No. 15, pp. 8970-8985) is cited to teach the electrochemical vanillin reduction in alkaline aqueous sodium hydroxide solution (page 8971, Scheme 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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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 The -CHO (aldehyde) in the formula is the non-halogen substituent.
2 -COOH is the carboxyl functional group, defining carboxylic acids.