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 .
DETAILED ACTION
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 11/11/2025 has been entered. A suspension of action was NOT requested.
Claim Status
Claims 1 and 6, 14-46 are pending. Claims 15-43 are withdrawn. Claims 1, 6, 14 and 44-46 are under examination in their entirety. Claims 1, and 45-46 are rejected. Claims 6 and 14 are objected to. Claim 44 is allowed.
Filing Receipt
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Election/Restrictions
Applicant elected Group I claims 1-14 without traverse in the reply filed on
07/16/2024.
Claims 15-43 are withdrawn from further consideration pursuant to 37 CFR
1.142(b), as being drawn to a nonelected invention, there being no allowable generic or
linking claim.
Specie Election
Applicant elected the following specie in the reply filed on 07/16/2024.
Fatty epoxide = 1,2-epoxytetradecane,
Olefin containing nucleophile = 2-allylphenol
Olefin-functional hydrophobe = 2-allylphenol-[1,2-epoxytetradecane(1)],
and Alkoxylate = 2-allylphenol-[1,2-epoxytetradecane(1)-EO(15)].
The specie election was withdrawn.
The elected specie is obvious. See below 103 rejections.
Response to Amendments/Arguments
Applicant's amendments and arguments filed 11/11/2025 are acknowledged and have been fully considered. The Examiner has re-weighed all the evidence of record. Any rejection and/or objection not specifically addressed below in original or modified form is herein withdrawn.
Withdrawn/Modified Rejections
The 112(a) and 112(b) rejections of claim 13 in the final mailed 08/12/2025 are withdrawn. Claim 13 is cancelled.
The 102 rejection of claims 1, 4 and 8 as anticipated by Joyabu et al. (WO2018/061533 published 04-2018, English equivalent USPGPub2019/0217265) in the final mailed 08/12/2025 is withdrawn. The claim amendments have overcome the rejection.
The 103 rejection of claim 5 over Ogasawara et al. (USPGPub2014/0249272 Published 11-2013) and Joyabu et al. (WO2018/061533 published 04-2018, English equivalent USPGPub2019/0217265) as applied to claims 1, 4 and 8 and in further view of Kim et al. (Allyl/propenyl phenol synthases from the creosote bush and engineering production of specialty/commodity chemicals, eugenol/isoeugenol, in Escherichia coli, Archives of Biochemistry and Biophysics, 541, pp 37-46, Published 2014) in the final mailed 08/12/2025 is withdrawn.
Response to Arguments
Applicant's arguments filed 11/11/2025 have been fully considered but they are not persuasive.
Arguments concerning the reference Kim are moot. The reference Kim is not being applied in any rejection in this office action.
Concerning rejection D in the applicant’s remarks page 11, a “lack of clarity” is not being utilized in the current rejections.
Concerning the explanation as to why one skilled in the art would immediately choose the allyl phenol among the various possibilities in paragraph 30 of Ogasawara et al., the current rejection utilizes KSR established obvious to try and substitution.
Concerning the applicant’s assertion that Ogasawara et al. and Joyabu et al. are limited to molecules bearing allyl ethers as reactive moieties, applicant has not supplied a teaching to substantiate this assertion. Alternatively, if the teachings of Ogasawara et al. and Joyabu et al. point to allyl ethers, these teachings would be considered preferences.
See MPEP 2123 II. “Disclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or nonpreferred embodiments.”
Concerning the styryl phenyl, this appears to be a property of the allylphenols which were successfully argued to have been obvious. Properties cannot be excluded from the compounds in the prior art. "Products of identical chemical composition cannot have mutually exclusive properties." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). A chemical composition and its properties are inseparable. Therefore, if the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present. MPEP 2112.01 II.
Moreover applicant argues there is a potential that some or all of the reactive surfactants have styrenic reactive double bonds. A potential is just that, and not a requirement.
Concerning the 170,000 scifinder hits of a molecule having an alcohol and an allylphenyl group, a search of the isomers of unsubstituted allylphenols that only have one allyl group and one OH group would definitely not return the voluminous number of hits described by applicant. Moreover hits may be understood as references or molecules and if dimers, trimers, oligomers/polymers are included in the search there is a potential for a large amount of hits.
The claimed reactive surfactants were rendered obvious by the prior art, no impermissible hindsight was used.
In response to applicant's argument that the examiner's conclusion of obviousness is based upon improper hindsight reasoning, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971). In the instant case, the prior art teach the reaction of a fatty epoxide having the claimed number of carbons, a olefin-functional nucleophile and the product thereof being reacted with ethylene oxide. The claimed ally-substituted phenol and 1,2-epoxytetradecane are additionally taught. Impermissible hindsight was not utilized.
Concerning the purported unexpected result, the comparative reactive surfactant is not one from the closest prior art. A comparative example from the closest prior art may include working example [2] paragraph 69 of Ogasawara et al. Wherein an epoxide having 14 carbons is reacted with allyl alcohol and the product thereof is reacted with 20 moles of EO. For example, establishing a criticality of the claimed ally-substituted phenol and/or 1,2-epoxytetradecane over the taught allyl alcohol and/or C12/C14 epoxy would have carried more weight in trying to establish an unexpected
result.
The current comparative examples involve 4-nonylphenol-2-(1-propen-1-yl)
polyoxylene 10 EO for 7L and nonylphenol EO10 for 5L. These surfactants are not the
reactive surfactants in the working examples of the closest prior art.
Moreover, Ogasawara et al. teaches away from the nonyl phenols in paragraph 24.
For the reasons stated above the obviousness rejection is maintained/modified as set forth below.
Claim Interpretation
An allyl-substituted phenol is being interpreted as a phenol substituted with an allyl group. However, this interpretation does not necessarily exclude a substituted allylphenol as depicted in working example 24 of the current specification.
A definition of allyl-substituted phenol is not provided in the specification.
However working example 20 on page 37 depicts 2-allylphenol as seen immediately below.
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The above phenol is an allyl substituted phenol in the 2 position.
Moreover, as seen on page 17 wherein a propenyl-substituted phenol is reacted with a fatty epoxide, the following compound is produced.
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From the above, a propenyl-substituted phenol would necessarily be the compound immediately below.
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Therefore similarly from above, an allylphenol would necessarily be the claimed allyl-substituted phenol.
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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim(s) 1 is/are rejected under 35 U.S.C. 103 as being unpatentable over Ogasawara et al. (USPGPub2014/0249272 Published 11-2013) and Joyabu et al. (WO2018/061533 published 04-2018, English equivalent USPGPub2019/0217265)
Scope of the Prior Art
Ogasawara et al. broadly teach the immediately below reactive emulsifier (par. 69).
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Wherein the reactive emulsifier is exemplified to be prepared by first reacting a fatty epoxide having 12 to 14 carbons (isopentadecene oxide) with an Olefin-functional nucleophile (allyl alcohol). With a subsequent reaction of the product (olefin-functional hydrophobe) with ethylene oxide. See Ogasawara et al. paragraph 71.
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Concerning the claimed 1,2-epoxytetradecane, the immediately above variable R5 being C12 encompasses the claimed 1,2-epoxytetradecane. Seen immediately below.
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However without specificity, the variable R5 being C12 can and does encompasses isopentadecene as taught by Ogasawara et al.
Concerning the allyl-substituted phenol, Ogasawara et al. more broadly teach the immediately below formula (1) which encompasses the disclosed allyl alcohol (par. 29-30). Ogasawara et al. goes on to teach the compound of formula (1) to be substituted on an aromatic group, for example allylphenyl (par. 29-30). Wherein n is one and R1 is H.
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To ensure the reactivity of the allylphenyl group with the epoxide having
12 to 14 carbons, as allyl alcohol does, the allylphenyl group would necessarily be the claimed allyl-substituted phenol.
Ascertain the Differences
The above methods of Ogasawara et al. differ from the claimed invention due to a lack of a teaching of 1,2-epoxytetradecane.
Secondary References
Joyabu et al. teach overlapping reactive surfactants and methods of making as
compared to the current specification and with respect to Ogasawara et al. See immediately below.
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The C12H25 alkyl on the above reactive surfactant is necessarily prepared by the reaction of allyl alcohol with 1,2-epoxytetradecane. With a subsequent reaction involving ethylene oxide.
The above teachings of the secondary reference overlap with the teachings of the primary reference and render the secondary reference analogous art to the invention.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have combined the teachings of Ogasawara et al. and Joyabu et al. to arrive at the current invention with a reasonable expectation of success.
For example, it would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have tried other C12 epoxides encompassed by the teachings of Ogasawara et al. To do so, the ordinary artisan would have looked to and tried the 1,2-epoxytetradecane as taught by Joyabu et al. in the methods to prepare a reactive surfactant taught by Ogasawara et al. with a reasonable expectation of success. The reasonable expectation of success from the 1,2-epoxytetradecane taught by Joyabu et al. is encompassed by the variable R5 a C12 in the reactive emulsifier taught by Ogasawara et al. (par. 69). Additionally, the success from the fact that both Ogasawara et al. and Joyabu et al. teach overlapping reactive emulsifiers that employ identical ingredients, allyl alcohol, C12 epoxides and ethylene oxide. See MPEP 2141 III (A-E).
Moreover, it would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have substituted the isopentadecene oxide taught by Ogasawara et al. with the 1,2-epoxytetradecane taught by Joyabu et al. in the methods to prepare a reactive surfactant taught by Ogasawara et al. with a reasonable expectation of success. The ordinary artisan would have done so to substitute one known method for another to obtain predictable results See MPEP 2141 III (A-E).
The ordinary artisan would have looked to Joyabu et al. and would have combined the teachings with Ogasawara et al. due to the overlapping subject matter and because Joyabu et al. being analogous art the invention.
Next, it would have been prima facie obvious for an ordinary artisan before the
effective filing date of the claimed invention to have substituted the allyl alcohol taught
by Ogasawara et al. with the allyl-substituted phenol taught by Ogasawara et al.
The ordinary artisan would have done so with a reasonable expectation of success because Ogasawara et al. teach the compound of formula (1) may be substituted on an aromatic group, for example allylphenyl. In doing so the ordinary artisan would have arrived at the current invention. To ensure the reactivity of the allylphenyl group with the epoxide having 12 to 14 carbons, as allyl alcohol does, the allylphenyl group would necessarily be the claimed allyl-substituted phenol.
Claim(s) 1, and 45-46 is/are rejected under 35 U.S.C. 103 as being unpatentable over Ogasawara et al. (USPGPub2014/0249272 Published 11-2013), Joyabu et al. (WO2018/061533 published 04-2018, English equivalent USPGPub2019/0217265) and Oldenhove (US Patent 6,908,890, Patent date 06-2005).
Scope of the Prior Art
The individual and combinational teachings of Ogasawara et al. and Joyabu et al. in the above 103 rejection are incorporated by reference. Additional teachings of Ogasawara et al. are as follows. Alkylene oxides and phenols are shown to react. See paragraphs 34 and 42-46 of Ogasawara et al.
Concerning the EO(15) of claim 46, Ogasawara et al. teach working examples of reactive emulsifiers having 10 and 20 moles EO respectively (par. 68 and 69). These boundaries of moles of EO encompass the claimed 15 moles of EO.
Ascertain the Differences
Ogasawara et al. and/or Joyabu et al. do not explicitly recite the claimed 2-allylphenol.
Secondary References
Oldenhove teach 2-allylphenol (current claim 45) and 4-allylphenol (column 2, lines 12-18). 2-allylphenol and 4-allylphenol overlap in scope with the compound of formula (1) taught by Ogasawara et al. (par. 29-30). Wherein n is one and R1 is H.
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The above teachings of the secondary reference overlap with the teachings of the primary reference and render the secondary reference analogous art to the invention.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have tried the 2-allylphenol and/or 4-allylphenol with 1,2-epoxytetradecane and finally EO in the process to prepare the reactive emulsifier via the combinational teachings of Ogasawara et al. and Joyabu et al. with a reasonable expectation of success. See MPEP 2141 III (A-E).
The ordinary artisan would have done so to satisfy a source of the allylphenyl group in formula (1) taught by Ogasawara et al. The reasonable expectation of success from the fact that alkylene oxides and phenols are shown to react. See paragraphs 34 and 42-46 of Ogasawara et al.
The ordinary artisan would have looked to Oldenhove and would have combined the teachings therein with Ogasawara et al. due to the overlapping subject matter and because Oldenhove being analogous art the invention.
Concerning the olefin-functional hydrophobe, upon reacting the 2-allylphenol with the 1,2-epoxytetradecane as argued above, the claimed olefin-functional hydrophobe would have necessarily been prepared. Finally, reacting the EO(15) would have been obvious due to the combination.
Concerning the EO(15) of claim 46, MPEP 2144.05 II. A. and B. “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to BLAINE G DOLETSKI whose telephone number is (571)272-2766. The examiner can normally be reached M-F 7-4 EST.
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/B.G.D/Examiner, Art Unit 1692 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625