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 .
Note: The previous office action mailed on 9 March 2026 is vacated and replaced with a revised office action.
Election/Restrictions
Claims 10-11 withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 18 September 2025.
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.
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.
Claims 1–9 is/are rejected under 35 U.S.C. § 103 as being unpatentable over Gaonkar et al. (US 2014/0065282, hereafter “US ’282”) in view of KR 10-2010-0026208 (hereafter KR ’208) and further in view of KR 10-2017-0114812 (hereafter KR’812).
US ’282 discloses making coffee-derived surfactants by alkaline-catalyzed transesterification of sugars with coffee oil. See US ’282, p. 2, ¶[0008]–¶[0009] (coffee-derived surfactants prepared by transesterification of sugars and coffee oil; alkaline catalyst such as potassium carbonate). US ’282 further discloses use of alkaline transesterification catalysts including K2CO3, KOH, NaOH, Na2CO3, KHCO3, and NaHCO3. See US ’282, p. 3, ¶[0016]. US ’282 also discloses conducting the transesterification in a suitable solvent (e.g., dimethylformamide) at about 130–170°C for about 4–10 hours. See US ’282, p. 3, ¶[0017]. US ’282 exemplifies reacting sucrose with spent grounds coffee oil in the presence of K2CO3 catalyst in dimethylformamide at about 135°C for 8 hours to yield sucrose fatty acid ester products. See US ’282, p. 3, ¶[0021].
Claim 1 differs from US ’282 in that claim 1 requires (i) transesterifying coffee-derived oil with a short-chain alcohol and a basic catalyst to form an unsaturated fatty acid alkyl ester, (ii) hydrogenating the unsaturated fatty acid alkyl ester (fully or partially) to form a saturated fatty acid alkyl ester, and (iii) sulfonating the saturated (or partially saturated) fatty acid alkyl ester to form a fatty acid alkyl ester sulfonate.
KR ’208 discloses, in the manufacture of MES (alpha-methyl ester sulfonate), first transesterifying oils with a primary alcohol to synthesize an unsaturated fatty acid alkyl ester, then hydrogenating the unsaturated fatty acid alkyl ester to remove more than 99.9% of double bonds to synthesize a saturated fatty acid alkyl ester having an iodine value of 0.1 or less, and then sulfonating the saturated fatty acid alkyl ester to manufacture MES. See KR ’208, p. 3 (manufacturing sequence; iodine value 0.1 or less; sulfonation to make MES). KR ’208 also explains why hydrogenation to remove double bonds is performed before sulfonation/sulfation (double bonds cause discoloration/by-products; excessive alkali in neutralization; complicated purification/deodorization), and states it is important to synthesize saturated fatty acid alkyl esters having an iodine value of 0.1 or less (near complete hydrogenation). See KR ’208, p. 3.
It would have been obvious to one of ordinary skill in the art at the time that the invention was made to modify the coffee-oil transesterification product route of US ’282 to include the hydrogenation and subsequent sulfonation steps as taught by KR ’208, because KR ’208 discloses these steps as conventional processing sequences for converting fatty acid alkyl esters derived from oils into sulfonated surfactants (MES), and identifies hydrogenation (to very low iodine value) as a known way to mitigate sulfonation problems attributable to unsaturation. Employing KR ’208’s conventional MES processing to a coffee-oil-derived ester feedstock would have been a predictable substitution of one oil-derived ester feedstock for another in the same type of downstream hydrogenation/sulfonation chemistry.
Claims 2 and 3 further recite carbon-chain distributions for the fatty acid component (C14–C20) as “main component” limitations.
KR ’812 discloses that coffee oil extracted from coffee grounds has a fatty-acid carbon-chain distribution as shown in Table 1, including C16 (26–30%), C18 (5–7%), C18:1 (6–8%), C18:2 (43–54%), C18:3 (~2–3%), and C20/C20:5 (7–20%), and describes that C20 is present at a relatively high rate depending on coffee type. See KR ’812, ¶[0014]–¶[0015] and Table 1. In view of KR ’812’s disclosure of coffee-oil chain-length distributions, it would have been obvious that using coffee oil as the oil feedstock in the US ’282 with the KR ’208 process would yield ester intermediates (and resulting sulfonates) having C14–C20 chain lengths as the dominant range, and that confirming/selecting coffee oils meeting a specified distribution is routine characterization for natural-oil feedstocks.
Claim 4 limits the hydrogenation step by an iodine-number requirement consistent with complete or partial hydrogenation.
KR ’208 discloses hydrogenating an unsaturated fatty acid alkyl ester to remove more than 99.9% of double bonds and to obtain a saturated fatty acid alkyl ester having an iodine value of 0.1 or less, and further explains the importance of such low iodine value for avoiding sulfonation-related discoloration/by-products and downstream processing burdens. See KR ’208, p. 3. Thus, the iodine-number limitation is taught as a conventional, result-effective control of hydrogenation extent in the same MES process context.
Claims 5 and 6 limit the basic catalyst and alcohol used in the transesterification step.
US ’282 discloses alkaline transesterification catalysts including K2CO3, KOH, NaOH, Na2CO3, KHCO3, and NaHCO3. See US ’282, p. 3, ¶[0016]. Theses catalysts for transesterification is disclosed by US ’282. To the extent claim 1 requires use of a short-chain alcohol as the transesterification alcohol, KR ’208 discloses transesterifying oils with a primary alcohol, and identifies primary alcohols having 1 to 4 carbon atoms (methyl, ethyl, propyl, butyl alcohol) for synthesizing unsaturated fatty acid alkyl esters from oils. See KR ’208, p. 12 (primary alcohol having 1–4 carbon atoms; examples).
Claim 7 recites a mole ratio of saturated fatty acid alkyl ester to sulfonating agent of 1:1 to 2.
KR ’208 discloses sulfonating the saturated fatty acid alkyl ester to manufacture MES. See KR ’208, p. 3. Selection/adjustment of reactant molar ratios for sulfonation to reach effective conversion while managing side reactions is an established optimization variable in sulfonation processes. In the absence of evidence that the claimed ratio produces an unexpected result, the recited range represents routine optimization of a process parameter associated with the taught sulfonation step.
Claim 8 requires that the fatty acid alkyl ester sulfonate has C16 and/or C18 as a main component and contains C20 at about 1–10 wt.%.
KR ’812 discloses that coffee oil includes substantial C16 and C18-family components and includes C20/C20:5 at 7–20% depending on coffee type (Table 1). See KR ’812, ¶[0014]–¶[0015] and Table 1. Therefore, when coffee oil is used as the starting oil in the US ’282 transesterification and then processed by KR ’208’s hydrogenation and sulfonation sequence, the resulting ester/sulfonate products would predictably reflect the underlying chain-length distribution of the coffee oil feedstock, i.e., predominance of C16/C18 components with a C20 fraction. Achieving a narrower C20 subrange (such as 1–10 wt.%) would have been an expected matter of selecting a coffee oil source with lower C20 content within the disclosed variability, or blending/fractionating coffee oils—routine feedstock selection practices for natural oils.
Claim 9 merely changes the sequence of the fist and second steps so that hydrogenation is performed earlier (on the coffee-derived oil) to reduce the degree of unsaturation before the alcohol/base-catalyzed transesterification step. KR’208 discloses the recognized need to reduce double bonds/unsaturation to avoid known adverse effects during sulfonation (e.g. side reactions at double bonds leading to discoloration and byproducts) and therefore motivates lowering unsaturation prior to the sulfonation stage.
A person of ordinary skill in the art, would have found it an obvious process-implementation choice to shift the hydrogenation earlier in the process (i.e., hydrogenate the oil feedstock before transesterification) because doing so predictably produces a more saturated ester mixture downstream and advances the objective already relied upon in the rejection (minimizing unsaturation-driven issues in subsequent sulfonation). KR’812 supports that coffee oil includes unsaturated components and that its composition is measurable/predictable, reinforcing the routine nature of adjusting saturation at the feedstock stage.
In accordance with KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398 (2007), the claimed subject matter is the obvious use of prior art elements according to their established functions. US ’282 supplies the coffee-oil-derived transesterification starting point and surfactant context, KR ’208 supplies the well-known reasoned sequence of hydrogenation (to reduce unsaturation and improve sulfonation behavior) followed by sulfonation to produce ester sulfonate surfactants, and KR ’812 supplies the known compositional characteristics of coffee oil relevant to the claimed chain-length limitations.
The combination therefore represents no more than the application of a known technique (hydrogenation/sulfonation of fatty acid alkyl esters) to a known, analogous feedstock (coffee oil) to obtain the expected surfactant product, with a rational underpinning grounded in the references rather than hindsight
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.
Claim 3 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.
Claim 3 recites that the oil comprises “0.1 to 10% by weight of a C14 fatty acid” (along with the C16/C18/C20 ranges). The specification describes the coffee-derived oil as containing “0.01 to 1% by weight of a C14 fatty acid,” with the other ranges substantially aligned.
The specification does not reasonably convey possession of a coffee-derived oil having a C14 fatty acid content up to 10 wt.% as recited in claim 3. The disclosed upper bound for C14 is 1 wt.%, and the claim’s broadened upper range (10 wt.%) is not supported in the written description as filed.
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.
Claims 1-8 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.
Claim 1 is indefinite because the term “short-chain alcohol” is a relative term that fails to provide an objective boundary in the claim. Claim 1 recites “adding a short-chain alcohol” without specifying the carbon-number range or otherwise defining “short-chain.”
The specification does describe that the alcohol used “is a C1–C4 alcohol” and provides examples (methanol, ethanol, propanol, butanol). However, that definition is not recited in claim 1, and claim scope must be clear from the claim language. As presently drafted, claim 1 does not particularly point out the subject matter regarded as the invention.
Claim 2 is indefinite because the phrase “as a main ingredient” is subjective and lacks an objective standard or measurable threshold. Claim 2 recites that the oil comprises a C14–C20 unsaturated fatty acid “as a main ingredient,” without specifying what “main” means (e.g., at least 50 wt.%, largest peak area by GC, etc.) or how it is determined.
The specification likewise uses “as a main component” language (e.g., “a C16–C18 unsaturated fatty acid as a main component”) without defining a quantitative boundary for “main.” Accordingly, the limitation does not distinctly define claim scope.
Claim 8 is indefinite because it recites that the fatty acid alkyl ester sulfonate “comprises a C16 or C18 moiety as a main ingredient and 1 to 10 wt.% of a C20 moiety,” but does not identify what structural fragment “moiety” refers to or the analytical basis for the “wt.%” measurement.
While the specification discusses “alkyl chain” distributions (C14/C16/C18/C20) and repeatedly associates the carbon number with fatty-acid-derived chains in the MES context, the claim itself does not specify whether the C16/C18/C20 refers to the fatty-acyl chain, the alcohol-derived alkyl group, or some other fragment of the molecule. The lack of this anchor renders the scope uncertain.
Claims 3–7 is rejected as being dependent upon a rejected base claim.
Specification
The use of the terms, “Terg-O-tometer” (washing test apparatus), “WFK10D,” “WFK20D,” and “WFK, Germany” (stained cloth products/vendor identifiers), “Colorimeter Nippon Denshoku, D65/10” (instrument/vendor identifier), which is a trade name or a mark used in commerce, has been noted in this application. The term should be accompanied by the generic terminology; furthermore the term should be capitalized wherever it appears or, where appropriate, include a proper symbol indicating use in commerce such as ™, SM , or ® following the term.
Although the use of trade names and marks used in commerce (i.e., trademarks, service marks, certification marks, and collective marks) are permissible in patent applications, the proprietary nature of the marks should be respected and every effort made to prevent their use in any manner which might adversely affect their validity as commercial marks.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DEBORAH D CARR whose telephone number is (571)272-0637. The examiner can normally be reached Monday-Friday (10:30 am -6:30 pm).
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/DEBORAH D CARR/Primary Examiner, Art Unit 1691