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
Claim Status
Claims 1, 6, and 14-46 are pending. Claims 15-43 are withdrawn. Claims 1, 6, 14 and 44-46 are under examination in their entirety. Claims 1, 6, 14 and 45-46 are rejected. Claim 44 is allowed.
Filing Receipt
PNG
media_image1.png
120
1004
media_image1.png
Greyscale
PNG
media_image2.png
92
998
media_image2.png
Greyscale
PNG
media_image3.png
78
998
media_image3.png
Greyscale
PNG
media_image4.png
72
1002
media_image4.png
Greyscale
PNG
media_image5.png
46
994
media_image5.png
Greyscale
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Claims 15-43 are withdrawn from further consideration pursuant to 37 CFR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The specie election was withdrawn.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 06/23/2026 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 Any rejection and/or objection not specifically addressed below in original or modified form is herein withdrawn.
Withdrawn/Modified Rejections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 103 rejection of claim 1 over Ogasawara et al. (USPGPub2014/0249272 Published 11-2013) and Joyabu et al. (WO2018/061533 published 04-2018, English equivalent USPGPub2019/0217265) in the non-final mailed 03/23/2026 is has been modified to address the newly added claim limitations. The modifications were necessitated by amendment.
The 103 rejection of claims 1, and 45-46 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) in the non-final mailed 03/23/2026 is has been modified to address the newly added claim limitations. The modifications were necessitated by amendment.
The newly added 112(a) written description rejection was necessitated by amendment.
Response to Arguments
Applicant's arguments filed 06/23/2026 have been fully considered but they are not persuasive.
Applicant argues the prior art does not teach the isomerization of an ally group. The below rejections successfully address the new isomerization limitation.
Concerning the allylphenol, the below rejections successfully argue the obviousness of the allylphenol.
Concerning applicants arguments wherein Ogasawara et al. teach the allyl starting material as seen immediately below, the starting material does not prevent
PNG
media_image6.png
208
485
media_image6.png
Greyscale
the preparation of the isomer. As will be argued in the below rejections the reactions in the prior art and in the current invention, utilize basic conditions. Thus, the isomerization would have occurred.
Concerning the argument that one skilled in the art would not reasonably expect that the claimed alkoxylate produced in step (b) could comprise a propenyl group formed by the isomerization of an allyl group, the environment of the claimed reaction. As will be argued below, the basic environment of the reactions in the prior art provides for the conditions for isomerization.
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.
PNG
media_image7.png
75
124
media_image7.png
Greyscale
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.
PNG
media_image8.png
290
248
media_image8.png
Greyscale
From the above, a propenyl-substituted phenol would necessarily be the compound immediately below.
PNG
media_image9.png
125
91
media_image9.png
Greyscale
Therefore similarly from above, an allylphenol would necessarily be the claimed allyl-substituted phenol.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 1, 6, 14 and 45-46 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
The claims are rejected under 112(a) for lacking written description for the claim limitation of “wherein the alkoxylate produced in step (b) comprises a propenyl group formed by isomerization of an allyl group of the allyl-substituted phenol”.
The original disclosure does have support for the isomerization of 2-allylphenol in step (a) of claim 1. See page 6 of the specification which recites “The original 2-allyl group in many cases rearranges partially or completely under the reaction conditions”. The rearrangement is occurring during the reaction of the 2-allylphenol and the fatty epoxide (1,2-epoxytetradecane). This correlates to step (a). In step (a) basic conditions are present during the isomerization (p. 24 specification, lines 10-19). Note: “the reaction conditions” that cause the rearrangement/isomerization of the 2-allyl group are not defined on page 6 of the specification.
The art verifies basic conditions are utilized for the isomerization. See Marteau et al. (Boosting effect of ortho-propenyl substituent on the antioxidant activity of natural phenols, Food Chemistry, 196, pp. 418-427, Published 2016). Marteau et al. teach KOH/methanol environment during isomerization of a 2-allyl-substituted phenol (p. 419).
Contrary to the isomerization occurring in step (a) on page 6 of the specification, the specification on page 24 recites the isomerization is occurring in the step that correlates to current step (b). Note: step (a) page 24 of the specification does not confirm the existence of the isomer even with H-NMR spectroscopy is utilized.
In summary, the specification presents isomerization may be occurring in either
current step (a) and/or (b). The art suggests the isomerization is occurring in current step (a). This brings into question when the isomerization is occurring.
Additionally, concerning the isomerization of any and all ally-substituted phenols in step (b) of claim 1, the original disclosure is lacking support.
Applicant points to page 24, lines 29-31, and page 44, lines 10-13 of the specification in the reply mailed 06/23/2026 for support of the newly added limitation.
The specification on page 24 has the reaction of 2-allyphenol with 1,2-epoxytetradecane and ethylene oxide. This reaction does lead to the isomerization of the allyl group to the propenyl group.
The specification on page 44 lines 10-13 has the immediately below reaction (following page) depicting what appears to be a Claisen rearrangement with allyl isomerization to propenyl. See p. 4, lines 24-27 of the specification for discussions of Claisen rearrangement.
PNG
media_image10.png
191
525
media_image10.png
Greyscale
The above reaction is not occurring during the current step (b) as claimed. No alkoxylation is occurring.
Moreover, the words isomerization, isomeric, isomer, rearranges and/or rearrangement are recited a total of seven times in the current specification. Out of the seven references, only two references are made to an isomerization of 2-allylphenol during step (b) as currently claimed. The remaining recitations are not referencing isomerization of an allyl group of the allyl-substituted phenol during an alkoxylation.
Another allyl-substituted phenol, eugenol does not appear to undergo isomerization under basic conditions in the reaction recited in Example 19 page 37. Herein, this reaction mirrors current step (a) and the reaction of 2-allylphenol and the fatty epoxide (1,2-epoxytetradecane) on page 6.
Additionally, the alkoxylated product of eugenol lacks the propenyl. See surfactant 3S page 52. Wherein eugenol-[1,2-epoxytetradecane(1)-EO(16)-SO3NH4(1)] is not described to have the propenyl arm. Note: the specification does argue the names of the reactants are used when naming the product (p. 6). However, the specification lacks support for the isomerization of eugenol and for any other ally-substituted phenol beside 2-allyphenol.
Upon careful review of the specification the 2-allylphenol was contemplated to rearrange partially or fully to the propenyl isomer in step (a) possibly step (b). However, no other allyl-substituted phenol was contemplated to undergo isomerization in the alkoxylation step (b) of claim 1.
The art, Cerveny et al. (Isomerization of Eugenol to Isoeugenol, React. Kinet. Catal. Lett., vol. 33, No. 2, pp. 471-476, Published 1987) suggests eugenol can be isomerized to the propenyl isomer isoeugenol via the so-called alkaline version (p. 471). However, many factors including solvent, temperature, molar ratios and presences of water can affect the reaction (p. 471).
At the time of the filing of the invention any and all allyl-substituted phenols were not contemplated to rearrange/isomerize to the propenyl isomer in step (b) as currently claimed. Yes, the art suggests at least 2-allylphenol and eugenol can be isomerized to the propenyl isomer. However, written description for isomerizing any and all allyl-
substituted phenols in step (b) of claim 1 is lacking in the specification.
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). The modifications to this rejection were necessitated by amendment.
Scope of the Prior Art
Ogasawara et al. broadly teach the immediately below reactive emulsifier (par. 69).
PNG
media_image11.png
85
298
media_image11.png
Greyscale
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.
PNG
media_image12.png
138
497
media_image12.png
Greyscale
PNG
media_image13.png
132
490
media_image13.png
Greyscale
Concerning the claimed 1,2-epoxytetradecane, the immediately above variable R5 being C12 encompasses the claimed 1,2-epoxytetradecane. Seen immediately below.
PNG
media_image14.png
89
674
media_image14.png
Greyscale
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.
PNG
media_image15.png
74
455
media_image15.png
Greyscale
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.
PNG
media_image16.png
152
508
media_image16.png
Greyscale
PNG
media_image17.png
109
494
media_image17.png
Greyscale
PNG
media_image18.png
116
499
media_image18.png
Greyscale
PNG
media_image19.png
112
499
media_image19.png
Greyscale
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.
Concerning the claimed isomerization, this would have occurred. Ogasawara et al. teach the reaction of the fatty epoxide with the olefin-functional nucleophile in basic conditions (par. 71). Per the above arguments in the written description rejection, basic conditions are needed to isomerize the 2-allylphenol. Due to the method steps of the prior art and those currently utilized being substantially identical, the products would have been substantially identical.
Substantially identical methods yield substantially identical products. See MPEP 2112.01 I. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). "When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not." In re
Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990).
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). The modifications to this rejection were necessitated by amendment.
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.
PNG
media_image15.png
74
455
media_image15.png
Greyscale
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).
Concerning the claimed isomerization, this would have occurred. Ogasawara et al. teach the reaction of the fatty epoxide with the olefin-functional nucleophile in basic conditions (par. 71). Per the above arguments in the written description rejection, basic conditions are needed to isomerize the 2-allylphenol. Due to the method steps of the prior art and those currently utilized being substantially identical, the products would have been substantially identical.
Substantially identical methods yield substantially identical products. See MPEP 2112.01 I. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). "When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not." In re
Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990).
Allowable Subject Matter
Claim 44 is allowable.
The following is an examiner’s statement of reasons for allowance: The closest prior art to the invention is Ogasawara et al. (USPGPub2014/0249272 Published 11-2013).
Ogasawara et al. teach glycidyl ethers. See paragraphs 0029-50 when explaining the structures of the reactive emulsifiers of Formulas (1)-(3). Note: the reactive emulsifier of Formula (1) is being utilized to reject current claim 1.
However, nowhere in Ogasawara et al. is there a teaching of reacting a fatty
epoxide and a glycidyl ether with a olefin-functional nucleophile..
Therefore it would not have been obvious to have modified the prior art to arrive at the invention. There being no motivation to do so.
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 BLAINE G DOLETSKI whose telephone number is (571)272-2766. The examiner can normally be reached M-F 7-4 EST.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at (571)270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/B.G.D/Examiner, Art Unit 1692 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625
Prosecution Insights