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 .
Response to Amendment
The amendment to the claims and specification filed April 6, 2026 have been entered. Claims 1, 3-4, 6, 13-14, have been amended, claim 15 has been cancelled. Applicant’s amendments to the claims have overcome the objections to the claims and specification, the 112b, 112d rejections previously set forth in the Non-Final Office Action mailed December 5, 2025. Applicants cancellation of claim 15 have rendered the corresponding rejections/objections moot. As such, these rejections and objections are hereby withdrawn.
Applicant’s arguments filed April 6, 2026 were fully considered but they were not persuasive. Maintained/modified rejections necessitated by Applicant’s amendment are addressed below.
Claims 1-14 and 16-19 are pending in this application.
Election/Restrictions
Applicant’s election without traverse of Group I claims 1-15 (drawn to an oil resistant agent and products) in the reply filed on October 10, 2025 is acknowledged. Thus, claims 16-19 are withdrawn due to being directed to a non-elected invention and claim 15 has been cancelled. Thus claims 1-14 are examined herein.
Priority
This application is a CON of PCT/JP2022/024780 filed June 21, 2022 and claims foreign priority to JP 2022-019806 filed February 10, 2022 and JP 2021-103440 filed June 22, 2021. Acknowledgment is made of applicant’s claim for foreign priority under 35 U.S.C. 119 (a)-(d). The certified copy has been received. The Examiner notes that no English translation was provided.
Claim Interpretation
Claim 1 recites an oil-resistant agent, comprising a modified natural product. The broadest reasonable interpretation of the oil-resistant agent, is the modified natural product itself. According the instant specification the oil-resistant agent exhibits oil resistance and imparts the oil resistance to a treatment target by treating the treatment target with the oil-resistant agent (pg. 4, para. 0010) That is, the phrase “oil-resistant” is merely a description of a property of the agent or a property that occurs following application. Additionally the property of a given agent cannot be separated from the product given an identical product is taught in the prior art.
Modified Claim Rejections - 35 USC § 103
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.
Claim 1-3, and 5-14 are rejected under 35 U.S.C. 103 as being unpatentable over Nakagawa (CN 112779772, cited in previous action).
Regarding claims 1-3 and 5-14: Nakagawa teaches a water repellent composition comprising a dehydration condensate of a 2-to-4 membered polycarboxylic acid and a hydrocarbon alcohol or amine wherein the alkyl group has 6 to 22 carbon atoms (English translation, abstract). According to the instant specification, the instant oil-resistant agent can be used as a water repellant (pg. 62, lines 1-4). Nakagawa teaches the specific preparation: citric acid monohydrate reacted with dihydrotallow amine (trade name “Armeen 2HT”) in a condensation reaction forming a diamide compound as the main component (English translation, pg. 13, second to last para., production example 1). According to Nouryon, Armeen 2HT is a dialkyl amine of formula R-NH-R wherein R is an alkyl chain mainly C16-C18 (pg. 1, para. 1). Nakagawa teaches the resulting condensate (a1) has a melting point of 52-56 °C (English translation, pg. 13, second to last para., production example 1, i.e. higher than 25 °C). The condensate (a1) is then combined with an anionic surfactant and emulsified to prepare an aqueous dispersion (English translation, pg. 13, second to last para., production example 1). Nakagawa teaches in view of emulsifiability of the product, the components are adjusted so that least 1 carboxyl group form an ester/amide, and at least 0 to 1 carboxyl group remains unreacted (English translation, pg. 5, middle of page, para. 9). Unreacted carboxyl groups can be in the form of a carboxyl group, or exist as a salt of the carboxyl group (English translation, pg. 5, para. 13). Although Nakagawa does not determine the bio-based percentage of the product, considering a majority of the carbons are from bio-based ingredients (i.e. tallow), and not petroleum sources (instant specification, pg. 5, para. 0011) it is presumed to be higher than 30% as instantly claimed, absent evidence to the contrary. Although, Nakagawa is directed towards the application of the repellent towards fibers, as discussed above in the claim interpretation, the “intended use” of a composition or product, e.g., “for paper”, will not further limit claims drawn to a composition, so long as the prior art discloses the same composition comprising the same ingredients in an effective amount, as the instantly claimed. Thus, claim 15 is also anticipated. Nakagawa teaches the composition can further include pH adjusters, including citric acid (English translation, pg. 9, second to last para., pg. 10, para. 2), thereby anticipating claim 12.
However, Nagakawa teaches stearyl amine can be used as an alternative to dihydrotallow amine (English translation, pg. 5, para. 4). Given that they are possible alternatives encompassed by the formula of Nagakawa, it is prima facie obvious to substitute equivalents known for the same purpose (See MPEP 2144.06 (II)).
Taken together it would have been prima facie obvious to arrive at a citric acid modified with stearyl amine as taught by Nagakawa. A person of ordinary skill in the art would have had the motivation to do so with a reasonable expectation of success as Nagakawa teaches stearyl amine as a suitable alternative and it is prima facie obvious to substitute equivalents known for the same purpose.
According to the instant specification, Example 1 is prepared from the reaction between citric acid and octadecyl amine (i.e. stearylamine, pgs. 49-50, para. 0125). This example results in the formation of citric acid in which carboxylic acid groups have been replaced with octadecyl amides (i.e. stearyl amine connected to a carboxyl group). The instant specification demonstrates that the contact angle of this compound is 46.5 and has a melting point of 100 °C (pg. 51, para. 0128, table 1). The instant specification states the biobased content is 100 % (pgs. 49-50, para. 1, example 1).
Thus, wherein it would have been obvious to substitute dihydrotallow amine with stearyl amine, a person of ordinary skill in the art would be motivated to arrive at Example 1 as described in the instant specification, which necessarily has a contact angle, melting point, and biobased content within the claimed range, absent evidence to the contrary.
Claims 1, 3-8 and 13-14 are rejected under 35 U.S.C. 103 as being unpatentable over Rodriguez Gonzales (WO 2010/101477, cited in previous action), hereinafter referred to as Rodriguez.
Regarding claims 1, 3-8 and 13-14: Rodriguez teaches compounds and compositions of citric acid trialkylamides (citramides) for controlling gas hydrate formation (abstract, pg. 1, lines. 1-4). Rodriguez teaches the citric acid derivatives have the following formula:
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(pg. 6, lines 1-8). Rodriguez teaches tributyl citrate and acetyl tributyl citrate as possible compounds (pg. 10, lines 15-21, table 1). These compounds meet the structural limitations as recited by instant claims 1 and 3-8. Rodriguez teaches the compounds are to be dissolved in water at 1-2 wt% (pg. 18, bottom of page). Although, Rodriguez is directed towards the application of the agent for controlling gas hydrate formation as discussed above in the claim interpretation, the “intended use” of a composition or product, e.g., “for paper”, will not further limit claims drawn to a composition, so long as the prior art discloses the same composition comprising the same ingredients in an effective amount, as the instantly claimed. According to the instant specification, Example 1 is prepared from the reaction between citric acid and octadecyl amine (i.e. stearylamine, pgs. 49-50, para. 0125). This example results in the formation of citric acid in which carboxylic acid groups have been replaced with octadecyl amides (i.e. stearyl amine connected to a carboxyl group). The instant specification demonstrates that the contact angle of this compound is 46.5 and has a melting point of 100 °C (pg. 51, para. 0128, table 1). Given that the trialkyl citramides encompassed by Rodriguez are similar in structure to those in the instant specification, the compounds encompassed by Rodriguez meet the structural limitations of the instant claims and thus necessarily have a melting point >60 °C and HD contact angle of 10 degree or larger absent evidence to the contrary.
Response to Arguments
Applicant’s arguments filed April 6, 2026 with respect to the claims have been fully considered but they are not persuasive.
On pages 11 (last para.) and 12 (para. 1) of Applicant’s response, Applicant argues the compound of Nakagawa is a long-chain dialkyl amine, wherein the examples of the present application use a monoalkyl amine rather than a dialkylamine, and amended claim 1 limits some of R11 and R12 in the linker moiety to those having 4 or fewer carbon atoms. On page 12 of Applicant’s response, Applicant argues the amended claim recites that the oil resistant agent has a melting point of 60 C or higher, distinguishing from Nakagawa (para. 3).
However, see modified 103 rejections above, wherein the prior art renders obvious a composition comprising the claimed compound which has the claimed properties.
On page 12 of Applicants Response, Applicant argues that the present specification demonstrates excellent oil resistance, especially high temperature oil resistance (para. 5). Applicant argues the melting point of the oil-resistant agent in the above range improves resistance to temperature (para. 5). In short applicant argues that the high melting point accounts for its improved temperature resistance Applicant argues that the documents do not mention oil resistance, only referring to water repellency which are based on different mechanism and could not have been predicted (last para.).
However, these features are innate features to the compound. Additionally, the instant specification demonstrates static contact angle and melting point for two specific compounds, so even if the argument were found to be persuasive, the argued unexpected results are not commensurate with the scope of the claims (See MPEP 716.02(d).
Applicant’s reply is considered to be a bona fide attempt at a response and is being accepted as a complete response. The 35 USC § 103 rejections are maintained for reason of record and foregoing discussion.
Conclusion
No claims are allowed in this action.
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.
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/S.L.G./Examiner, Art Unit 1693
/ANDREA OLSON/Primary Examiner, Art Unit 1693
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