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 .
Status of Claims
The examiner acknowledges the amendments to claims 1-3 and 9 as well as the addition of claims 15-22 and the cancelation of claims 4-5 and 10. Claims 13-14 are withdrawn. Claims 1-3, 6-9, 11-12, and 15-22 are pending.
Specification
Applicant has amended the abstract. As a result, the previous objection to the specification is withdrawn.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1-3, 6-9, 11-12, and 15-22 are rejected under 35 U.S.C. 103 as being unpatentable over Suzuki (JP 2018-090492, Foreign Reference #1 from IDS dated 5/9/2024).
Regarding Claims 1-3, 12, 15-16, 18-20, and 22,
Suzuki teaches the fluorination of a compound with the following structure:
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in which R contains 2 or 3 carbons (Paragraph 9) which is contained within the range of the instant claim and in which the number of repeating units is from 4 to 20 (Paragraph 9), which overlaps with the range of the instant claim. Suzuki further teaches that R1 and R2 represent protecting groups for the hydroxyl group. One of ordinary skill in the art would recognize that the number of repeat units would, by necessity, alter the molecular weight of the polymer and it would logically follow, associated properties of that polymer including viscosity and boiling point. The ordinarily skilled artisan would choose the number of repeat units in the polymer to obtain a material with the desired material properties such as viscosity and boiling point that are suitable for the use case. As such, it would have been obvious prior to the effective filing date of the instant application to have selected any number of repeating units within the range that afforded a final polymer with the desired properties and it further would have been obvious to have selected the overlapping portion of the ranges because the selection of overlapping portions of ranges has been held to be a prima facie case of obviousness. See MPEP 2144.05.I.
With regard to step 1, Suzuki teaches in example 1 the use of material that is comprised only of polyethylene glycol of 7 and 8 repeat units (Paragraph 52). While Suzuki does not teach a molecular weight distribution adjustment to this material, Suzuki demonstrates using material with a narrow molecular weight distribution. Because polymerization reactions typically result in a spread of molecular weights, it would logically follow that this material had been adjusted to be a mixture of only the two identified species. As such, this step was performed even if it was not disclosed by Suzuki, meeting the requirements of the instant claim. Furthermore, as Suzuki teaches the use of a material with a narrow molecular weight range, it would logically follow that this adjustment could be conducted at any point in the process. It would therefore have been obvious prior to the effective filing date of the instant application to have conducted this adjustment at any point during the process. See MPEP 2144.04.IV.C. The examiner also points out that while the method described by the applicant indicates the addition of additional polyether compounds, the language used (5% or less and 15% or less) does not include a lower bound, which would indicate that the addition of these compounds is optional and is therefore not addressed here.
Suzuki additionally teaches that the compound is fluorinated with an inert gas and fluorine gas in a reactor with the reactant polymer in solvent (Paragraph 15).
Finally, Suzuki teaches that the protecting groups are preferably acyl groups (Paragraph 10).
Regarding Claim 6,
Suzuki teaches the use of polyethylene glycol (PEG) of 7 and 8 repeat units (Example 1, Paragraph 52), which would represent the mixture of two monodisperse PEG polymers, meeting the requirements of the instant claim.
Regarding Claim 7,
Suzuki teaches the use of polyethylene glycol (PEG) of 7 and 8 repeat units (Example 1, Paragraph 52). As noted in regard to claim 1 above, polymerization reactions typically result in a range of molecular weights. Because Suzuki teaches a starting PEG polymer that only contains polymer of 7 and 8 repeat units, it would logically follow that the composition was adjusted in a way to remove both the high and low molecular weight components and would therefore meet the requirements of the instant claim.
Regarding Claims 8-9,
Suzuki teaches in example 1 (Paragraph 52) a mixture of polyethylene glycol polymers that are 7 and 8 and repeat units. While Suzuki does not specify the ratio of the two polymers, the value of the molecular weight of the 8 repeat unit polymer divided by that of the 7 repeat unit polymer is 1.13. It would logically follow that the polydispersity of this mixture (Mw/Mn) would be lower than this value, since it would not be possible for the weight average molecular weight to exceed the value of the highest molecular weight polymer nor for the number average molecular weight to be below that of the smallest molecular weight polymer. Therefore, this mixture would meet the requirements of claim 8. With regard to the amounts of material that are above 4 repeat units beyond the average or with only 1 or two repeat units, because Suzuki specifies that the polyethylene glycol polymers (which is a homopolymer) are 7 or 8 repeat units, it would necessarily follow that these amounts would be zero, thereby meeting the requirements of claim 9.
Regarding Claim 11,
Suzuki teaches that inert gas and fluorine gas are introduced into the reactor (Paragraph 38) and that during this step, a perhalogenated unsaturated compound is added (Paragraph 41) with the preferred example of the compound being hexafluorobenzene (Paragraph 42).
Regarding Claims 17 and 21,
Suzuki teaches the use of polyethylene glycol in the method that is 7 and 8 repeat units and discussed above in regard to claim 1. As this polymer has only two different chain lengths, it would necessarily meet the requirement of a Mw/Mn of 1.3 or less.
Response to Arguments
Applicant's arguments filed 7/20/2026 have been fully considered but they are not persuasive for at least the following reasons.
On page 14, the applicant argues that commercial polyethylene glycol (PEG) can have molecular weight variability and therefore the material of Suzuki does not necessarily meet the material requirements of the claims. The examiner disagrees, as Suzuki specifies the chain length. Furthermore, monodisperse PEG has long been known and various methods to make monodisperse PEG have been disclosed in the literature dating back to at least 1992 (see Kinbara Polymer Journal article, art not cited). Additionally, Kinbara notes that monodisperse PEG as a requirement for pharmaceuticals incorporating a PEG into the structure with a reference to 2011. As such, monodisperse PEG is well known in the art and would have been commercially available prior to the publication of Suzuki and as a result, when Suzuki specifies the chain length, it would logically follow that the Mw/Mn would meet the requirements.
Also on page 14, the applicant argues that Suzuki does not teach how to perform the molecular weight adjustment nor at which point this step is performed. As noted in the rejection, the use of material with defined chain lengths would obviate the need for the practitioner to have performed this step themselves. Furthermore, as the material used already met the requirements, it would logically follow that a step to narrow the molecular weight range had been performed, regardless of whether it was disclosed and regardless of the method used. As it relates to the ordinarily skilled artisan not being instructed when to perform this operation, the order in which the operations were conducted is obvious to do in any order (see MPEP 2144.04.IV.C) and based upon the disclosure of the use of PEG with a defined chain length would clearly indicate that such a step had been performed prior to the fluorination reaction, as the applicant requires.
In summation, the applicant’s arguments are directed towards the molecular weight distribution of the PEG raw material used in the fluorination reaction and whether Suzuki teaches a distribution or method that the applicant uses in the instant application. However, the examiner points out that in order for the method used to adjust the molecular weight distribution to be sufficiently differentiated from the prior art, the applicant would need to present evidence that the adjustment method provides different results from other methods. This is especially true given that the applicant’s method in the instant claims involves only the optional addition of more PEG polymer, as noted in the rejection above and reiterated here. As this addition is optional, it leaves the use of PEG that already meets the requirements of the instant claims as possible. Furthermore, as the method describes the addition of polymer that is structurally the same as that to which it is being added, save the molecular weight, this adjustment step is analogous to adjusting the purity of the starting material which would not result in a raw material that differs from that which is disclosed by Suzuki.
Ultimately, the applicant’s arguments are not considered to be persuasive because the use of well-defined PEG polymer in a fluorination reaction is taught in the prior art as disclosed by Suzuki which the applicant, while disclosing a method to obtain well defined PEG polymer, has not demonstrated to result in a PEG material that is different from that taught by Suzuki even though Suzuki does not disclose how this well-defined PEG is obtained. As a result, the rejection is maintained.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Kinbara (Polymer Journal volume 50, pages 689-697 (2018 prior to the effective filing date of the instant application.
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 ADAM J BERRO whose telephone number is (703)756-1283. The examiner can normally be reached M-F 8:30-5.
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/A.J.B./Examiner, Art Unit 1765
/HEIDI R KELLEY/Supervisory Patent Examiner, Art Unit 1765
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