DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claims 1-14 and 16-25 are pending as amended on 11/13/2025. Claims 8, 10, 11 and 16-20 stand withdrawn from consideration.
The new grounds of rejection set forth below were necessitated by Applicant’s amendment which further narrows the molar ratio of C:A in claim 1, and which adds new claims 22-25. Therefore, this action is properly made final.
Any rejections and/or objections made in the previous Office action and not repeated below are hereby withdrawn. The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office Action.
Claim Rejections - 35 USC § 112
Claims 1-3, 6, 7, 9, 12-14 and 21-25 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 recites that compound B is an “aromatic alkoxide.” It is not clear what structure is intended by aromatic alkoxide. An alkoxide is not aromatic (because it must be derived from an alkyl alcohol). Claim 5 further limits compound B to phenoxide, which is not an “alkoxide,” and therefore it appears the term “aromatic alkoxide” is in error. For examination purposes, compound “B” has been interpreted as at least encompassing aromatic structures as recited in instant dependent claim 4. However, the term “aromatic alkoxide” in claim 1 should be replaced to clarify whether compound B recited in claim 1 encompasses non-aromatic alkoxides. Dependent claims (other than claims 4 and 5) are unclear for the same reason. Applicant may wish to consider replacing the term “aromatic alkoxide” in claim 1 with the chemical formula (III) defined in claim 4.
Additionally, claims 2 and 3 limit compound A to a chemical formula (II) which includes a group Ar, a group Zi and a group Ari. The claim defines Ar and Ari as “a divalent aromatic group,” defines Zi as an “oxygen atom, sulfur atom, alkylene group, carbonyl group or sulfonyl group.” The subscript “i” can be an integer ranging from 1 to 3. However, it is not clear what structure is implied by formula (II) when “i” is any integer other than 1.
For example, when “i” is equal to 2 (as recited in claim 3), the formula would be interpreted as: X1—Ar—[Z2—Ar2]n—X2. This formula could have been considered clearly understood, except that instant claim 3 (which defines “i” as 2) defines Ar1 as a phenylene group and Z1 as carbonyl. As set forth in the previous action, if “i” in formula (II) is 2, then there would be no Ar1 group or Z1 group in formula (II).
In response to the action mailed on 9/4/2025, Applicant argued (p 9 of remarks filed 11/13/2025) that when “i=2, there are two Z (Z1 and Z2) and two Ar (Ar1 and Ar2).” However, when a subscript is intended to indicate a number of repeating units, the subscript should be outside of brackets or parentheses which contain the structure to be repeated. Note, for example, that “n” in instant formula (II) properly indicates a number of repeating units and is just outside of brackets. In contrast, the subscript “2” of X2 is not outside of brackets/parentheses, because “X2” (like “X1”) is a single halogen atom. The group X2 does not denote that there is a group “-X1-X2” on the right side of formula (II).
Because it is unclear how to determine what structures are encompassed by instant formula (II) due to confusion surrounding the meaning of the group Zi and the group Ari, the scope of claims 2 and 3 are unclear.
Claim Rejections - 35 USC § 103
Claim(s) 23 and 24 is/are rejected under 35 U.S.C. 103 as being unpatentable over Hahn et al (US 5256826).
As to claims 23 and 24, Hahn discloses a process for preparing aromatic carbonyl compounds with an aryl ether structure by reacting phenols with halogenated carbonyl compounds in a dipolar aprotic solvent (col 1, lines 6-11).
As to instant compound A: Hahn teaches a halogen compound of formula IIIa, which has two halogenated aromatic groups. See col 4, lines 18-46.
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Hahn exemplifies 4,4-dichlorobenzophenone as the compound of formula IIIa (example 1). Hahn’s compound IIIa, including the exemplified dichlorobenzophenone, meet instant compound A.
As to instant compound B: Hahn teaches a phenol which has a formula II (col 4, lines 29-35), and exemplifies a reaction utilizing phenol and potassium carbonate (example 1) which forms phenoxide in situ, corresponding to instant compound B.
As to the molar proportion of B:A, Hahn teaches that the ratio of phenol II: dihalogen III is preferably 2.1:1 (col 5, lines 42-46; see also example 1), which falls within the presently claimed range of at least 2:1.
As to instant compound C: Hahn teaches several examples of suitable dipolar aprotic solvents, including acetonitrile, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide and sulfolane (col 3, lines 56-64; example 1) which correspond to compound C.
As to the molar proportion of C:A: Hahn teaches that the amount of solvent is from 200 to 1000% by weight of the phenol (col 5, lines 54-56).
Hahn exemplifies a reaction utilizing 24.2 grams (0.257 mol) of phenol. A range of the solvent NMP (as used in examples) in an amount of 200 to 1000 wt% of the phenol corresponds to a range of 48.4 g (200 wt% of phenol) to 242 g (1000 wt% of phenol) NMP. The molecular weight of NMP is 99 g/mol, which means that a range of 48.4 to 242 g NMP corresponds to a range of 0.489 to 2.44 mol of NMP. Therefore, for a reaction utilizing 0.257 mol phenol and 0.125 mol of dichlorobenzophenone (as in Hahn’s example 1), Hahn’s disclosed range of NMP (i.e., 200 to 1000 wt% phenol, which is 0.489 to 2.44 mol NMP) corresponds to a molar ratio of solvent:halogenated compound (i.e., C:A) ranging from 3.9:1 (i.e. 0.49/0.125) to 19.5:1 (i.e., 2.44/0/125), which overlaps the presently claimed range of not more than 7.5:1.
A prima facie case of obviousness is established where the claimed ranges overlap the ranges disclosed by the prior art. See MPEP 2144.05. Moreover, generally, differences in concentration will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration is critical. See MPEP 2144.05 I and II(A). When reacting dichlorobenzophenone and phenoxide in the presence of a reaction solvent, as taught by Hahn, one having ordinary skill in the art would have reasonably expected to achieve the result taught by Hahn (formation of aromatic carbonyl compounds with an aryl ether structure) when using any solvent content within the range taught by Hahn. Additionally, when carrying out a chemical reaction in organic solvent, the person having ordinary skill in the art would have been motivated to reduce the amount of solvent utilized in order to reduce solvent waste and costs associated with solvent use. It would have been obvious to the person having ordinary skill in the art, therefore, to have carried out Hahn’s reaction of dichlorobenzophenone with phenoxide in the presence of a solvent utilizing any amount within the range disclosed by Hahn, including an amount of solvent corresponding to a C:A (i.e., solvent:dichlorobenzophenone) ratio within the presently claimed range of not more than 7.5:1.
Claim(s) 1-7, 9, 12-14, 21, 22 and 25 is/are rejected under 35 U.S.C. 103 as being unpatentable over Hahn et al (US 5256826) in view of Matzner et al (US 5137988).
The rejection of claims 23 and 24 over Hahn is incorporated here by reference.
As to claim 25, Hahn suggests a method according to claims 23 and 24, as set forth above. Hahn teaches several examples of suitable dipolar aprotic solvents, including acetonitrile, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide and sulfolane (col 3, lines 56-64; example 1), however, Hahn fails to teach diphenyl sulfone as a solvent.
Matzner discloses a reaction which is similar to the reaction disclosed by Hahn, wherein a dihalobenzenoid compound (such as dichlorobenzophenone, col 6, line 40) is heated with a compound having phenolic groups (bisphenol) in the presence of base to produce an oligomer having an aryl ether structure (col 5, lines 49; col 6, lines 54-67). Matzner teaches that the reaction can be carried out in bulk, or in the presence of an inert solvent, and teaches aliphatic or aromatic sulfoxide or sulfone solvents as preferred. Preferred solvents include dimethyl sulfoxide, sulfolane and aromatic sulfones including diphenyl sulfone (col 7, line 64 to col 8, line 24).
Considering the general nature of Hahn’s disclosure with regard to solvent (see teaching to use “dipolar aprotic solvent” in col 1, lines 5-10) and the variety of solvents named by Hahn as being examples of suitable solvents (see col 3, lines 56-64), one having ordinary skill in the art would have had a reasonable expectation of success in carrying out Hahn’s disclosed reaction utilizing any dipolar aprotic solvent known in the art to be a suitable medium for the reaction of the chloro groups of dichlorobenzophenone with the phenolic groups of a phenolic compound, in the presence of a base, to produce aryl ether linkages. As evidenced by Matzner’s disclosure above, diphenyl sulfone was known in the art, along with solvents named by Hahn (e.g., dimethyl sulfoxide, sulfolane), as a suitable dipolar aprotic solvent for a reaction of dichlorobenzophenone with a phenoxide to form an aryl ether. It would have been obvious to the person having ordinary skill in the art, therefore, to have carried out the reaction of dichlorobenzophenone with phenoxide in the presence of a dipolar aprotic solvent, as taught by Hahn, by utilizing any dipolar aprotic solvent known in the art (and disclosed alongside dipolar aprotic solvents such as dimethyl sulfoxide and sulfolane named by Hahn) to be suitable for the type of reaction taught by Hahn, including diphenyl sulfone (DPS), as taught by Matzner. Case law has established that it is prima facie obvious to substitute one known element for another to obtain predictable results. KSR Int'l Co. v. Teleflex, Inc., 550 U.S. 398 (2007). MPEP 2143, rationale (B).
As to the molar proportion of C:A: Hahn teaches that the amount of solvent is from 200 to 1000% by weight of the phenol (col 5, lines 54-56). Hahn exemplifies a reaction utilizing 24.2 grams (0.257 mol) of phenol and 0.125 mol of dichlorobenzophenone. A range of the solvent diphenyl sulfone (DPS) in an amount of 200 to 1000 wt% of the phenol corresponds to a range of 48.4 g (200 wt% of 24.2 g phenol) to 242 g (1000 wt% of 24.2 g phenol) DPS. The molecular weight of DPS is 218.3 g/mol, which means that a range of 48.4 to 242 g DPS corresponds to a range of 0.22 to 1.1 mol of DPS. Therefore, for a reaction of 0.257 mol phenol with 0.125 mol of dichlorobenzophenone (as in Hahn’s example 1), Hahn’s disclosed range of solvent (i.e., 200 to 1000 wt% of phenol, which for DPS is 0.22 to 1.1 mol) corresponds to a molar ratio of solvent:halogenated compound (i.e., C:A) ranging from 1.8:1 (i.e. 0.22/0.125) to 8.8:1 (i.e., 1.1/0.125), which overlaps the presently claimed range of not more than 7.5:1.
A prima facie case of obviousness is established where the claimed ranges overlap the ranges disclosed by the prior art. See MPEP 2144.05. Moreover, generally, differences in concentration will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration is critical. See MPEP 2144.05 I and II(A). When reacting dichlorobenzophenone and phenoxide in the presence of a reaction solvent, as taught by Hahn, one having ordinary skill in the art would have reasonably expected to achieve the result taught by Hahn (formation of aromatic carbonyl compounds with an aryl ether structure) when using any solvent content within the range taught by Hahn. Additionally, when carrying out a chemical reaction in organic solvent, the person having ordinary skill in the art would have been motivated to reduce the amount of solvent utilized in order to reduce solvent waste and costs associated with solvent use. It would have been obvious to the person having ordinary skill in the art, therefore, to have carried out Hahn’s reaction of dichlorobenzophenone with phenoxide in a solvent utilizing any amount of solvent within the range disclosed by Hahn (1.8:1 to 8.8:1), including an amount of solvent corresponding to a C:A (i.e., solvent:dichlorobenzophenone) ratio within the presently claimed range of not more than 7.5:1.
As to claims 1-7, 9, 12, 14, 21 and 22, Hahn discloses a process for preparing aromatic carbonyl compounds with an aryl ether structure by reacting phenols with halogenated carbonyl compounds in a dipolar aprotic solvent (col 1, lines 6-11).
As to instant compound A: Hahn teaches a halogen compound of formula IIIa, wherein X (corresponding to “Z” in instant formula II) is carbonyl or sulfonyl, L (corresponding to Ari in instant formula II) can be phenylene and “n” can be 0 (meeting n=1 in instant formula II). See col 4, lines 18-46.
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Hahn exemplifies 4,4-dichlorobenzophenone as the compound of formula IIIa (example 1), which has a structure according to instant compound A recited in claims 1-3.
As to instant compound B: Hahn teaches a phenol which has a formula II (col 4, lines 29-35), and exemplifies a reaction utilizing phenol and potassium carbonate (example 1) which forms phenoxide in situ (as recited in claims 7 and 9), corresponding to instant compound B recited in claims 1, 4 and 5. The molar proportion of potassium carbonate reacted with phenol is 1:1 in example 1 (see also col 5, lines 47-48), meeting instant claim 12.
As to the molar proportion of B:A, Hahn teaches that the ratio of phenol II: dihalogen III is preferably 2.1:1 (col 5, lines 42-46; see also example 1), which falls within the presently claimed range of at least 2:1 (and less than 3:1, as recited in claim 6).
As to instant compound C: Hahn teaches several examples of suitable dipolar aprotic solvents, including acetonitrile, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide and sulfolane (col 3, lines 56-64; example 1).
However, Hahn fails to teach diphenyl sulfone as a solvent.
Matzner discloses a reaction which is similar to the reaction disclosed by Hahn, wherein a dihalobenzenoid compound (such as dichlorobenzophenone, col 6, line 40) is heated with a compound having phenolic groups (bisphenol) in the presence of base to produce an oligomer having an aryl ether structure (col 5, lines 49; col 6, lines 54-67). Matzner teaches that the reaction can be carried out in bulk, or in the presence of an inert solvent, and teaches aliphatic or aromatic sulfoxide or sulfone solvents as preferred. Preferred solvents include dimethyl sulfoxide, sulfolane and aromatic sulfones including diphenyl sulfone (col 7, line 64 to col 8, line 24).
Considering the general nature of Hahn’s disclosure with regard to solvent (see teaching to use “dipolar aprotic solvent” in col 1, lines 5-10) and the variety of solvents named by Hahn as being examples of suitable solvents (see col 3, lines 56-64), one having ordinary skill in the art would have had a reasonable expectation of success in carrying out Hahn’s disclosed reaction utilizing any dipolar aprotic solvent known in the art to be a suitable medium for the reaction of the chloro groups of dichlorobenzophenone with the phenolic groups of a phenolic compound, in the presence of a base, to produce aryl ether linkages. As evidenced by Matzner’s disclosure above, diphenyl sulfone was known in the art, along with solvents named by Hahn (e.g., dimethyl sulfoxide, sulfolane), as a suitable dipolar aprotic solvent for a reaction of dichlorobenzophenone with a phenoxide to form an aryl ether. It would have been obvious to the person having ordinary skill in the art, therefore, to have carried out the reaction of dichlorobenzophenone with phenoxide in the presence of a dipolar aprotic solvent, as taught by Hahn, by utilizing any dipolar aprotic solvent known in the art (and disclosed alongside dipolar aprotic solvents such as dimethyl sulfoxide and sulfolane named by Hahn) to be suitable for the type of reaction taught by Hahn, including diphenyl sulfone (DPS), as taught by Matzner. Case law has established that it is prima facie obvious to substitute one known element for another to obtain predictable results. KSR Int'l Co. v. Teleflex, Inc., 550 U.S. 398 (2007). MPEP 2143, rationale (B).
As to the molar proportion of C:A: Hahn teaches that the amount of solvent is from 200 to 1000% by weight of the phenol (col 5, lines 54-56). Hahn exemplifies a reaction utilizing 24.2 grams (0.257 mol) of phenol and 0.125 mol of dichlorobenzophenone. A range of the solvent diphenyl sulfone (DPS) in an amount of 200 to 1000 wt% of the phenol corresponds to a range of 48.4 g (200 wt% of 24.2 g phenol) to 242 g (1000 wt% of 24.2 g phenol) DPS. The molecular weight of DPS is 218.3 g/mol, which means that a range of 48.4 to 242 g DPS corresponds to a range of 0.22 to 1.1 mol of DPS. Therefore, for a reaction of 0.257 mol phenol with 0.125 mol of dichlorobenzophenone (as in Hahn’s example 1), Hahn’s disclosed range of solvent (i.e., 200 to 1000 wt% of phenol, which for DPS is 0.22 to 1.1 mol) corresponds to a molar ratio of solvent:halogenated compound (i.e., C:A) ranging from 1.8:1 (i.e. 0.22/0.125) to 8.8:1 (i.e., 1.1/0.125), which overlaps the presently claimed range of not more than 3:1.
A prima facie case of obviousness is established where the claimed ranges overlap the ranges disclosed by the prior art. See MPEP 2144.05. Moreover, generally, differences in concentration will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration is critical. See MPEP 2144.05 I and II(A). When reacting dichlorobenzophenone and phenoxide in the presence of a reaction solvent, as taught by Hahn, one having ordinary skill in the art would have reasonably expected to achieve the result taught by Hahn (formation of aromatic carbonyl compounds with an aryl ether structure) when using any solvent content within the range taught by Hahn. Additionally, when carrying out a chemical reaction in organic solvent, the person having ordinary skill in the art would have been motivated to reduce the amount of solvent utilized in order to reduce solvent waste and costs associated with solvent use. It would have been obvious to the person having ordinary skill in the art, therefore, to have carried out a reaction of dichlorobenzophenone with phenoxide in DPS as solvent utilizing any amount of solvent within the range disclosed by Hahn (i.e., 1.8:1 to 8.8:1), including an amount of solvent corresponding to a C:A (i.e., solvent:dichlorobenzophenone) ratio within the presently claimed range of not more than 3:1.
As to claim 13, diphenyl sulfone has a polarity greater than 3 Debyes (see, e.g., instant specification, p 5, lines 13-24).
Response to Arguments
Applicant's arguments filed 11/13/2025 have been fully considered.
In view of the amendments to the claims, the rejections under 35 USC 102 and 103 are overcome for the reasons set forth by Applicant, and have been withdrawn. New rejections under 35 USC 103 have been made.
Regarding the rejection under 35 USC 112(b):
Applicant argues (p 9) that an aromatic alkoxide is the conjugate base of an aromatic alcohol, such as phenol or substituted phenol. This argument is not consistent with the conventional definition of “alkoxide.” The conjugate base of phenol is phenoxide. The entry for “alkoxide” in the Oxford English Dictionary [“alkoxide (n.),” December 2025, https://doi.org/10.1093/OED/9093125222] is copied below:
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A similar definition for “alkoxides” is found in the IUPAC goldbook:
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Because an alkyl group cannot be aromatic, an alkoxide compound of the formula RO-, wherein R is an alkyl group, cannot be aromatic. Therefore, the claims stand rejected under 35 USC 112(b).
Applicant argues (p 9) that with regard to claim 3, when i=2, there are two Z and two Ar. This argument fails to overcome the rejection under 35 USC 112(b) for reasons which are adequately set forth in the rejection above.
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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL KAHN whose telephone number is (571)270-7346. The examiner can normally be reached Monday to Friday, 8-5.
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/RACHEL KAHN/ Primary Examiner, Art Unit 1766