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 .
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 04/23/2026 has been entered.
Applicants’ arguments, filed 04/23/2026, have been fully considered. Rejections and/or objections not reiterated from previous office actions are hereby withdrawn. The following rejections and/or objections are either reiterated or newly applied. They constitute the complete set presently being applied to the instant application.
Claim Rejections - 35 USC § 112 – Indefiniteness
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 1 is 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.
Instant claim 1 is indefinite because it recites, in part, “(R1-A)a-CH(R2)-…” wherein “a” is 1 or 2. The structure “(R1-A)2-CH(R2)-…” (i.e., “a” is 2) is not clear from the disclosure. For example, it cannot be the case that two “(R1-A)” groups are attached to the carbon of the adjacent CH(R2) when “a” is 2, because such a structure would violate the strict valency limit of carbon. Accordingly one must assume that the second “(R1-A)” group is attached to the first “(R1-A)” group. However, there is no indication as to where the second (R1-A) would attach in the event that “a” is 2. For the purposes of examination the Examiner will interpret the structure when “a” is 2 to by (R1-A)-(R1-A)-CH(R2) wherein (R1-A) may be attached to (R1-A) at any point.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claim 1 recites the broad recitation of wherein R is, for example, methyl (the smallest R group) and R4 is a linear alkyl having 1-8 carbons (i.e., total carbon in compound would be 12-26), and the claim also recites wherein the total carbon content is 12-19 which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
Claim Rejections - 35 USC § 112 – Scope of Enablement
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.
Claim 1 is rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, because the specification, while being enabling for Formula I when a is 1, does not reasonably provide enablement for Formula I when a is 2. Specifically, the claims indicate that when “a” is two there exists carbons with 5 bonds. The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make the invention commensurate in scope with these claims.
Factors to be considered in determining whether a disclosure meets the enablement requirement of 35 U.S.C. §112, first paragraph, have been described In re Wands, 8 USPQ2d 1400(1988). They are:
1. The breadth of the claims;
2. The nature of the invention;
3. The state of the prior art;
4. The predictability or lack thereof in the art
5. The level of skill in the art;
6. The amount of direction or guidance present;
7. The presence or absence of working examples;
8. The quantity of experimentation needed.
The breadth of the claims
The claims recite a very broad structure comprising unsaturated furans, partially hydrogenated furans, fully hydrogenated furans, or alkyl chains comprising alcohols, ketones and aldehydes.
The state of the prior art/ The predictability or lack thereof in the art
In view of the art, one would not have expected to form a compound having carbons bonded to 5 atoms, as implied by Formula I when “a” is 2. While such a concept was known, it was not trivial, as evidenced by Malhan et al. (Chemistry, 2023, v. 5, no. 2, p. 1113-1123) at the first paragraph: “The concept of five bonds to carbon became indispensable since the discovery of methanium ion (CH+5) in the laboratory in 1950 [1]. Recording the infrared spectra of this simple protonated methane molecule was quite challenging, as it took almost five decades from its discovery.”
The level of skill in the art
The level of skill would be high to make a compound comprising a carbon bonded to 5 atoms.
The amount of direction or guidance present
The specification does not give any guidance in this regard. The closest direction given is at page 2 of the specification as originally filed which discloses Formula I and discloses A may be “-(CH2)4-“. This, however, is not present in the claims, nor is there a proviso to only select “-(CH2)4-“ when “a” is 2.
The presence or absence of working examples
There are no working examples that specifically represent Formula I when “a” is 2.
The quantity of experimentation needed
Due to the lack of direction and working examples in the specification and the well known principle of a standard 4 bond carbon, undue experimentation would be required to reproduce invention as instantly claimed.
Conclusion
Due to the experimentation necessary to make Formula I when “a” is 2; the lack of direction/guidance presented in the specification regarding the specific structure; the unpredictability of the implied 5 carbon bond; the breadth of the claims, undue experimentation would be required of a skilled artisan to make the claimed invention in its full scope.
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
1) Claim 4 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Liu et al. (Green Chemistry, May 2019, v. 21, 3606-3614).
Liu discloses the following compound at page 3609 in Scheme 2:
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421
392
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The prior art anticipates instant claim 4 because it discloses a compound that reads on the structure of claim 4 when R1 is an alkyl group having 1 carbon atom and R4 is an alkyl group having 5 carbon atoms.
2) Claim 1 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Jaratjaroonphong et al. (European Journal of Medicinal Chemistry, 2014, v. 83, p. 561-568).
Jaratjaroonphong discloses a compound of the formula below, wherein the R group is CH3CH2 [p. 562, col. 1, Table 1, row 8].
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183
350
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The prior art anticipates instant claim 1 because it disclosed a compound of Formula IV, wherein R is an alkyl group having 2 carbons, R4 is an alkyl group having 1 carbon and wherein the total carbon count is 12.
3) Claim 3 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Heinz et al. (Energy & Fuels, 2013, v. 27, p. 985-996).
Heinz discloses that algal triglycerides were converted to n-alkanes [abstract], Heinz reports that after completion of the first pass conversion of algal triglycerides, that “[t]he normal alkanes attributable to the C16 and C18 fatty acids, n-C15, n-C16, n-C17, and n-C18, account for between 96% and >99% of the recovered normal alkanes in each receiver” [p. 990, col. 2, first full para.].
The prior anticipates the instant claims because it discloses n-C17 alkane which reads on the structure of claim 3 when R is H and R4 is an alkyl chain having 4 carbons. Because the prior art is fully derived from algal triglycerides one would have expected it to meet the required bio-based carbon content of instant claim 3.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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.
1) Claims 1-3, and 5 are rejected under 35 U.S.C. 103 as being unpatentable over Saha et al. (WO 2019/036663 A1, publication date 02/21/2019; cited in IDS 08/07/2023) in view of Gore et al. (Biotribology, 2018, v. 16, p. 17-24).
Regarding instant claim 1 (Formula (I)), 2 and 5, Saha discloses a compound that has a biobased content between 10 and 100% according to ASTM-D6866 (i.e., instant claim 5) [p. 17, lines 27-33], with the formula (R1-A)b-(CHx)a-(CHR2)m-(C(R4Rs) )n-(CHR3)o-(CHy )c-(A-R1')d [p. 3, line 16]. Saha discloses that “b” may be 1, “a” may be 0, “m” may be 1, “n” may be 1, “o” may be 1, “c” may be 0, “d” may be 1 and R4-5 may be H [p. 3, lines 17-23]. Accordingly, Saha discloses the formula (R1-A)-(CHR2)-(CH2)-(CHR3)-(A-R1') wherein R1-3 may be alkyl groups having 1 to 18 carbon atoms (i.e., instant claim 2), R1 and R1’ may be the same and A is independently an unsaturated furan ring, a partially saturated furan ring or a saturated furan ring [p. 3, lines 26-30]. Finally, Saha discloses the total carbon content is in the range of 20 to 62 [p. 3, lines 32-33]. Finally, Saha discloses “the present invention, as disclosed hereinabove, may be used in pharmaceutical formulations and personal care product formulations, e,g, sunscreen, lotion, creams, cosmetics, and the like” [p. 20, lines 10-12] and desires “tailored molecular architecture, tunable properties and content” [p. 2, lines 26-27].
The disclosure of the prior art formula does not anticipate the instant claims because it does not have a total carbon count between 10 and 19.
Gore relates to the impact of the oil phase on the spreading behavior of cosmetic formulations [title]. Gore discloses that “[i]n general, constituents with low molecular weights and/or low viscosities have higher spreading properties. Thus, the choice of emollients is essential to control the efficacy of the product in terms of skin moisturizing, but also to achieve the satisfactory physical and chemical stability of the emulsion” [p. 17, sentences spanning columns 1 and 2].
It would have been obvious to one of ordinary skill in the art, before the effective filling date of the claimed invention, to have made the compound of Saha with a total carbon count within instantly claimed amounts through routine optimization. It has been held that it is not inventive to discover the optimum workable ranges by routine experimentation where, as is here, the general conditions of the claim are disclosed in the prior art. In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). One of ordinary skill in the art would have been motivated to optimize the total carbon count to find the optimal spreading properties in order to achieve satisfactory physical and chemical stability of emulsions. One would have had an expectation of success because Saha desires compounds with adjustable molecular architectures and properties.
Furthermore, given the disclosure of each component individually, it would have been prima facie obvious for a person having ordinary skill in the art at, at the time of filling, to have selected and combined known components for their established functions with predictable results by following the teachings of Saha. MPEP 2143 and 2144.06(I). Therefore it, would have been obvious for one of ordinary skill in the art, at the time of filling, to have formulated the compound described above to have a bio-based carbon content in the range of 30 to 100%, as instantly claimed (i.e., instant claim 5).
Regarding instant claims 1 (Formula (II)) and 3, Saha discloses a compound that has a biobased content between 10 and 100% according to ASTM-D6866 [p. 17, lines 27-33] with the formula (R1-A)b-(CHx)a-(CHR2)m-(C(R4R5) )n-(CHR3)o-(CHy )c-(A-R1')d [p. 3, line 16]. Saha discloses that “b” may be 1, “a” may be 0, “m” may be 4, “n” may be 1, “o” may be 4, “c” may be 0, “d” may be 1 and R1, R1’, R2, R3 and R4 may be H [p. 3, lines 17-23]. Accordingly, Saha discloses the formula (A)-(CH2)4-(CHR5)-(CH2)4-(A) wherein R5 is an alkyl group having 1 to 18 carbons and A is independently an unsaturated furan ring or a saturated furan ring [p. 3, lines 15-35].
The disclosure of the prior art formula does not anticipate the instant claims because it does not have a total carbon count between 10 and 19.
Gore relates to the impact of the oil phase on the spreading behavior of cosmetic formulations [title]. Gore discloses that “[i]n general, constituents with low molecular weights and/or low viscosities have higher spreading properties. Thus, the choice of emollients is essential to control the efficacy of the product in terms of skin moisturizing, but also to achieve the satisfactory physical and chemical stability of the emulsion” [p. 17, sentences spanning columns 1 and 2].
It would have been obvious to one of ordinary skill in the art, before the effective filling date of the claimed invention, to have made the compound of Saha with a total carbon count within instantly claimed amounts through routine optimization. It has been held that it is not inventive to discover the optimum workable ranges by routine experimentation where, as is here, the general conditions of the claim are disclosed in the prior art. In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). One of ordinary skill in the art would have been motivated to optimize the total carbon count to find the optimal spreading properties in order to achieve satisfactory physical and chemical stability of emulsions. One would have had an expectation of success because Saha desire compounds with adjustable molecular architectures and properties.
Furthermore, given the disclosure of each component individually, it would have been prima facie obvious for a person having ordinary skill in the art at, at the time of filling, to have selected and combined known components for their established functions with predictable results by following the teachings of Saha. MPEP 2143 and 2144.06(I). Therefore it, would have been obvious for one of ordinary skill in the art, at the time of filling, to have formulated the compound described above to have a bio-based carbon content in the range of 30 to 100%, as instantly claimed.
2) Claim 4 is rejected under 35 U.S.C. 103 as being unpatentable over Saha et al. (WO 2019/036663 A1, publication date 02/21/2019; cited in IDS 08/07/2023).
Saha also discloses a compound with the formula (R1-A)b-(CHx)a-(CHR2)m-(C(R4R5) )n-(CHR3)o-(CHy )c-(A-R1')d, wherein “m” is 0, “b” is 2, “a” is 1, “o” is 1 and “c” is 0. [p. 3, lines 17 and 22]. This yields the formula (R1-A)2-(CH)-(CR4R5)-(CHR3)-(A-R1'), wherein R1, R1’, R4 and R5 may be H, R3 may be an alkyl group having 1-18 carbon atoms and A is independently an unsaturated furan ring, a partially saturated furan ring or a saturated furan ring [p. 3, lines 24-29].
While the formula of the prior art encompasses structures of instant claim 4, it does not anticipate the instant claims as it does not specifically disclose the overlapping structures were synthesized.
However, given the disclosure of the overlapping general structure, it would have been prima facie obvious for a person having ordinary skill in the art at, at the time of filling, to have selected and combined known components for their established functions with predictable results by following the teachings of Saha to synthesize compounds of the instantly claimed Formula I. MPEP 2143 and 2144.06(I). Therefore it, would have been obvious for one of ordinary skill in the art, at the time of filling, to have synthesized (A)2-(CH)-(CH2)-(CHR3)-(A) wherein R3 may be alkyl groups having 1 to 18 carbon atoms, and A is independently an unsaturated furan ring or a saturated furan ring.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-5 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1, 4, 5, 7-9, 11, 13, 23, 33, 34, 36-40, 42-45 of copending Application No. 2021/0040055 A1 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because they both claim a bio-based compound with overlapping structures [claim 1]. For example, the formula of claim 1, (R1-A)b-(CHx)a-(CHR2)m-(C(R4Rs) )n-(CHR3)o-(CHy )c-(A-R1')d, wherein “b” may be 1 or 2, “a” may be 0, “m” may be 1, “n” may be 1, “o” may be 1, “c” may be 0, “d” may be 1 and R4-5 may be H. This yields the formula (R1-A)b-(CHR2)-(CH2)-(CHR3)-(A-R1') wherein R1-3 may be alkyl groups having 1 to 18 carbon atoms (i.e., instant claim 2), R1 and R1’ may be the same and A is independently an unsaturated furan ring, a partially saturated furan ring or a saturated furan ring. It would have been obvious to one of ordinary skill in the art, at the time of filling, to have made an instantly claimed compound because the claims of ‘055 disclose it. MPEP 2143
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Response to Arguments
1) On pages 12-13 of their Remarks, Applicant argues that one of
ordinary skill in the art would not have expected the claimed compounds to possess properties similar to those disclosed in Saha. Applicant cites the Declaration under 37 CFR 1.132; hereinafter “declaration.” Specifically, Applicant argues flashpoint and viscosity change with total carbon count and compounds with lower carbon numbers, e.g., those between 10-19 carbons, can possess significant structural differences when compared to compounds with total carbon contents above 19.
This argument is moot in view of the new rejections set forth above. While this argument is moot, the Examiner will note that Saha teaches substantially the same compounds as instantly claimed, differing only by 1 carbon in the total carbon content. The declaration asserts that compounds with 19 and 20 carbons would have different properties at paragraphs 15-18. However, it is not clear what compounds are represented by the flashpoint and viscosity graphs and if these graphs represent all claimed compounds differing from the prior art by 1 carbon.
2) On page 13 of their Remarks, Applicant argues structures disclosed in the application and total carbon contents ranging from 10 to 19 carbon atoms can produce cosmetic formulations with improved aesthetic properties and acceptable spread abilities when compared to cosmetic formulations containing similar structures with higher total carbon contents. Applicant cites the Declaration under 37 CFR 1.132; hereinafter “declaration.”
Evidence of secondary considerations, such as unexpected results or commercial success, is irrelevant to 35 U.S.C. 102 rejections and thus cannot overcome a rejection so based. In re Wiggins, 488 F.2d 538, 543, 179 USPQ 421, 425 (CCPA 1973). In the present case each independent claim is anticipated and therefore secondary considerations are irrelevant.
However, briefly, the Examiner will note that the evidence cited in the declaration does not establish a critical range and is not commensurate in scope with the claims. To establish unexpected results over a claimed range, applicants should compare a sufficient number of tests both inside and outside the claimed range to show the criticality of the claimed range. In re Hill, 284 F.2d 955, 128 USPQ 197 (CCPA 1960). (MPEP 716.02(d)). The evidence provided is for compounds with 17 carbons and 22 carbons. Applicant has not explained why compounds having 17 carbons represent compounds having 10 to 19 carbons, and why compounds having 22 carbon represent a range down to, and not beyond, 20 carbons. Accordingly, the Examiner can not determine the criticality of the range. Additionally, the examples do not include claimed compounds represent by the “RKunsat-“ of the instant disclosure and the claims do not recite specific formulations, which appear to affect the properties (i.e., see W/O emulsions and O/W emulsions on pages 4-5 of the Declaration). Additionally, instant claim 4 does not recited the carbon range asserted to be critical.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to COLMAN WELLES whose telephone number is (571)272-3843. The examiner can normally be reached Monday - Friday, 8:30am - 5:00pm ET.
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/C.T.W./Examiner, Art Unit 1612
/WALTER E WEBB/Primary Examiner, Art Unit 1612
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