DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 October 3, 2025, has been entered.
Claims 9-15 are cancelled. Claim 23 is new.
Claims 1-8 and 16-23 are pending and examined on the merits.
Specification
The disclosure is objected to because of the following informalities:
The disclosure is objected to because it contains an embedded hyperlink and/or other form of browser-executable code. Applicant is required to delete the embedded hyperlink and/or other form of browser-executable code; references to websites should be limited to the top-level domain name without any prefix such as http:// or other browser-executable code. See MPEP § 608.01.
The embedded browser-executable code is in the paragraph beginning at page 8, line 1, as set forth in the amendment to the specification filed March 12, 2025. When the browser-executable code is viewed via a web browser, it becomes a live web link, transferring the user to a commercial website. USPTO policy does not permit the USPTO to link to any commercial sites since the USPTO exercises no control over the organization, views or accuracy of the information obtained on those outside sites. See MPEP 608.01(VII).
Additionally, the specification is objected to because “www.gog.com” in the amendment to the specification filed March 12, 2025, opens to a website that does not involve GCG software package, contrary to the recitation “the GAP program in the GCG software package (available at…” preceding the browser-executable code.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
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 21 and 22 are 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.
Claims 21 and 22 are indefinite because the definition of “an average degree of esterification” of a sorbitol carboxylate is unclear. The specification as filed does not give a clear definition of the term with respect to a sorbitol carboxylate. Instead, the specification provides an example of steps taken to determine the average degree of esterification of the carboxylic esters of sorbitol present in the sorbitol carboxylate (page 12, lines 12-19). In particular, that passage states, “for example, by first determining the content of free sorbitol and its 1,4-anhydrosorbitol, 2,5-anhydrosorbitol, 1,5-anhydrosorbitol and isosorbide degradation products in a sample of the sorbitol carboxylate in question” (page 12, lines 12-15; emphasis added). Then, it is additionally necessary to determine the saponification value, acid value and content of free and neutralized fatty acids (page 12, lines 15-18). Also, an average molar mass of the carboxylic acid mixture that has been esterified is given which can then be used to calculate the average degree of esterification (page 12, lines 18-20). However, no explanation is given for how the average degree of esterification is calculated from the average molar mass of the carboxylic acid mixture that has been esterified. Since these teachings are provided in the specification only as an example and no explanation is given for the calculation of the average degree of esterification, then the metes and bounds of the term “average degree of esterification” are unclear.
Though “degree of esterification” is a known term in the art, the term has a definition such that the value cannot be numbers in the range of 1.1 to 4.0 or the range of 2.6 to 4.0 as recited in claims 21 and 22. For instance, Chatjigakis (Carbohydrate Polymers. 1998. 37: 395-408) defines “degree of esterification” as (number of esterified carboxylic groups/number of total carboxylic groups)
×
100 in the context of pectic molecules (page 395, second paragraph). The degree of esterification of Chatjigakis is in units of percentage (Figure 1 on page 397), which is contrary to the values recited claims 21 and 22.
Notice Re: Prior Art Available Under Both Pre-AIA and AIA
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.
Claim Rejections - 35 USC § 102
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.
Claims 1-8, 16, 17, 19, and 23 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Ducret (Biotechnology and Bioengineering. 1995. 48: 214-221. Listed on IDS filed 6/16/22), as evidenced by Kennedy (Journal of the European Ceramic Society. 2023. 43: 7146-7166).
Ducret discloses preparing biosurfactants by enzymatic esterification of sugars and sugar alcohols (abstract). In one experiment, the synthesis of the biosurfactants is without solvent, which meets the limitation of instant claim 23. See page 215, right column, ‘Synthesis Without Solvent’ section; and page 217, left column, second paragraph. In that experiment, sorbitol and oleic acid were mixed with Novozym 435, and the esterification reaction was carried out under reduced pressure at 90ºC to remove the water formed during the reaction, wherein Novozym 435 is Type B lipase from Candida antarctica immobilized on an acrylic resin (page 215, left column, second-to-last paragraph for description of Novozym 435). Oleic acid is directed to an acyl group donor, specifically meeting the limitation of a fatty acid as the at least one acyl group donor of instant claim 16.
Figure 1 shows the esters of sorbitol formed through this esterification reaction, including sorbitol monooleate, sorbitol dioleate, and sorbitol trioleate (page 217, left column, third paragraph). These esters of sorbitol are each directed to a ‘sorbitol carboxylate.’ Furthermore, Ducret teaches that the maximum concentration of monoesters was reached after 3 hours of reaction (page 217, left column, second paragraph). Figure 1 shows different reactions times up to 24 hours, e.g., 2, 3, 4, 6, and 24 hours, which result in producing the esters of sorbitol. The mixing of the sorbitol and oleic acid with Novozym 435 to synthesize esters of sorbitol at those reaction times as taught by Ducret anticipates the claimed method since it is directed to a process for enzymatic preparation of a sorbitol carboxylate, comprising:
A) blending sorbitol and at least one acyl group donor (oleic acid), at 90ºC (falling in the claimed range of 90ºC to 120ºC), for a time period falling in the claimed range of ‘at least 10 minutes’ (the reaction times taught in Ducret that include as low as 2 hours and as high as 24 hours),
B) reacting the sorbitol with the at least one acyl donor (oleic acid) in the presence of a lipase (Type B lipase from Candida antarctica) at 90ºC (falling in the claimed range of 75ºC to 110ºC), to give a sorbitol carboxylate (an ester of sorbitol, e.g., sorbitol monooleate, sorbitol dioleate, sorbitol trioleate).
As such, Ducret anticipates instant claims 1, 16 (a fatty acid), and 23.
Regarding instant claims 2 and 19, as evidenced by Kennedy, the chemical formula of oleic acid is C18H34O2 (page 7147, right column, Section 2.1). Therefore, the at least one acyl group donor of Ducret provides acyl groups that derive from a carboxylic acid containing 18 carbon atoms, falling in the claimed range of ‘2 to 34 carbon atoms.’ Thus, instant claim 2 is anticipated. Also, as evidenced by Kennedy, oleic acid is a natural fatty acid (abstract). Thus, instant claim 19 is anticipated.
Regarding instant claim 3, Ducret teaches mixing 1.290 g sorbitol with 2.000 g oleic acid and 0.5 g Novozym 435 (page 215, right column, ‘Synthesis Without Solvent’ section). Therefore, according to the calculation below, the sorbitol and the at least one acyl group donor (oleic acid) make up about 86.8% by weight, based on the overall reaction mixture at the start of B) (the reaction in the presence of a lipase), which falls within the claimed range of ‘at least 80% by weight.’ Thus, instant claim 3 is anticipated.
Calculation:
1.290
g
s
o
r
b
i
t
o
l
+
2.000
g
o
l
e
i
c
a
c
i
d
1.290
g
s
o
r
b
i
t
o
l
+
2.000
g
o
l
e
i
c
a
c
i
d
+
0.5
g
l
i
p
a
s
e
×
100
=
86.8
w
t
%
Regarding instant claim 4, as discussed above, the synthesis is performed without solvent. Since there is no solvent, then there is no water (which is known as a solvent). Furthermore, the esterification reaction is performed under reduced pressure at 90ºC to remove the water formed during the reaction (page 315, right column, ‘Synthesis Without Solvent’ paragraph). Therefore, the water content of the overall reaction mixture is 0% by weight which falls within the claimed range of ‘less than 15% by weight.’ As such, instant claim 4 is anticipated.
Regarding instant claim 5, as pointed out above, the lipase is Type B lipase from Candida antarctica (page 215, left column, second-to-last paragraph). Therefore, instant claim 5 (lipase B from Candida antarctica) is anticipated.
Regarding instant claim 6, the esterification reaction of Ducret is carried out under reduced pressure of < 0.7 kPa (page 215, right column, ‘Synthesis Without Solvent’ section). That pressure falls within the claimed range of ‘less than 1 bar’ (1 bar is well known in the art as converting to 100 kPa). Thus, instant claim 6 is anticipated.
Regarding instant claim 7, the esterification reaction times included reaction times up to 24 hours (e.g. 2 hours, 24 hours) that resulted in the esters of sorbitol (Figure 1). Each of these reaction times fall within the claimed range of ‘no later than 180 hours after the lipase has been added.’ Thus, instant claim 7 is anticipated.
Regarding instant claim 8, Ducret teaches mixing 7.09 mmol sorbitol with 7.09 mmol oleic acid in their experiment (page 215, right column, ‘Synthesis Without Solvent’ section), which is a 1:1 molar ratio of sorbitol to oleic acid. Oleic acid has a single acyl group so the molar ratio of the sorbitol provided to all acyl groups present in the at least one acyl group donor (oleic acid) provided is 1.00:1.00 which falls within the claimed range of ‘1.00:0.50 to 1.00:5.00.’ Thus, instant claim 8 is anticipated.
Regarding instant claim 17, as pointed out above, the esterification reaction was carried out at 90ºC (page 215, right column, ‘Synthesis Without Solvent’ section). The esterification reaction as catalyzed by the lipase (Novozym 435) is directed to step B) of the claimed invention, and 90ºC falls within the claimed range of ‘80ºC to 95ºC.’ Thus, instant claim 17 is anticipated.
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.
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 18 is rejected under 35 U.S.C. 103 as being unpatentable over Ducret (as evidenced by Kennedy) in view of Gruning (US 6,320,065).
As discussed above, Ducret (as evidenced by Kennedy) anticipates claims 1-8, 16, 17, 19, and 23. Regarding claim 18, Ducret teaches that the esterification reaction was carried out at 90ºC (page 215, right column, ‘Synthesis Without Solvent’ section), and the reaction times for producing the esters of sorbitol (each directed to a sorbitol carboxylate) include reaction times up to 24 hours. The mixing during the esterification reaction is directed to step A) of the claimed invention, so the duration of the mixing is as long the reaction times, such as 2 hours and 24 hours, which fall in the claimed range of ‘at least 60 minutes.’ However, Ducret differs from claim 18 in that Ducret does not expressly disclose that this mixing is at a temperature range of 100º to 120ºC.
Gruning discloses a process for the preparation of fatty acid partial esters of polyols having at least 4 C atoms, at least one primary and at least one secondary alcohol group of the starting polyols, where in a first process step the polyols are reacted with a fatty acid or a fatty acid derivative to give a fatty acid partial ester, and in a second process step the fatty acid partial esters obtained are subjected to a selective enzymatic cleavage of primary ester groups (column 2, line 66 through column 3, line 8). Gruning points out that it is possible to carry out the process according to their invention entirely without solvent (column 3, lines 14-16). Sorbitol is a preferred polyol (column 3, lines 36-50, in particular lines 44 and 50), and the fatty acid can be oleic acid (column 3, line 66 through column 4, line 7, in particular column 4, lines 6-7). Also, a lipase can be used for performing the enzymatic cleaving, with the immobilized thermostable lipase Novozyme® 435 being particularly preferred (column 4, lines 54-65). The first stage (step) of the process is carried out at 110 to 300ºC for 2 to 12 hours (column 4, lines 21-29; claim 20 of Gruning). In the case of the reaction of sorbitol in the first stage of the process, the preferred temperature range is from 110 to 150ºC (column 4, lines 38-40).
Before the effective filing date of the claimed invention, it would have been obvious to the person of ordinary skill in the art to react the sorbitol with the oleic acid at a temperature of 110 to 150ºC for 2 to 12 hours before mixing them with the Novozym 435 under reduced pressure at 90ºC when performing the method of Ducret. One of ordinary skill in the art would have been motivated to do this because it results in preparing fatty acid partial esters of polyols as indicated in Gruning, which are products sought in Ducret since Ducret discloses generating esters of sorbitol, and because Gruning teaches that this temperature and reaction time is preferred for the reaction of sorbitol with a fatty acid (e.g. oleic acid, which is the fatty acid reacted with sorbitol in Ducret) prior to reaction with a lipase that can be the lipase of Ducret (Novozym 435) for the purpose of preparing fatty acid partial esters of polyols. Moreover, it would have been an obvious matter of applying the known technique of Gruning (reaction of sorbitol with a fatty acid, e.g. oleic acid, at 110 to 150ºC for 2 to 12 hours prior to reaction with lipase, e.g. Novozym 435) to the base method of Ducret for the predictable result of preparing esters of sorbitol. There would have been a reasonable expectation of preparing esters of sorbitol by applying the technique of Gruning to Ducret because both Gruning and Ducret involve the same materials (sorbitol, fatty acid, lipase), and the invention of Gruning can be carried out entirely without solvent (column 3, lines 14-16), thereby conforming with the synthesis without solvent taught by Ducret. Since 110 to 150ºC overlaps with the claimed range of ‘100ºC to 120ºC’ and 2 to 12 hours falls within the claimed range of ‘at least 60 minutes,’ then instant claim 18 is rendered obvious.
Claim 20 is rejected under 35 U.S.C. 103 as being unpatentable over Ducret (as evidenced by Kennedy) in view of Teixeira Tage Biaggio (US 2011/0091946. Previously cited).
As discussed above, Ducret (as evidenced by Kennedy) anticipates claims 1-8, 16, 17, 19, and 23. Ducret differs from claim 20 in that Ducret does not expressly disclose that the sorbitol and the at least one acyl group donor (oleic acid) make up at least 95% by weight, based on the overall reaction mixture at the start of B). Instead, Ducret teaches that they make up about 86.8% by weight, based on the overall reaction mixture at the start of B) (see rejection of claim 3).
Teixeira Tage Biaggio discloses an enzymatic process for obtaining a fatty ester comprising reacting a fatty acid with a fatty alcohol which can be sorbitol, in the presence of an enzyme, in at least one reactor, at a temperature of from 40 to 80ºC (claim 1 of Teixeira Tage Biaggio). Preferably the enzyme is selected from lipases, and the lipase is preferably Novozymes® 435 (paragraph [0040]). In Example 3, the invention of Teixeira Tage Biaggio is performed using cupuacu fatty acid, sorbitol, and Novozymes® 435 enzyme (paragraph [0071]). In that example, the fatty acid was previously melted, the bath was activated at 70ºC, the fatty acid and the sorbitol were added when the bath temperature reached a particular temperature, and the enzyme was added to the reactor (paragraphs [0072]-[0075]). Additionally, Example 3 lists the weights of the cupuacu fatty acid, sorbitol, and Novozyme® 435 for the reaction (paragraph [0071]). According to the calculation below, the sorbitol and the fatty acid make up about 96% by weight, based on the overall reaction mixture that includes the lipase, which falls within the range of ‘at least 95% by weight’ of instant claim 20.
Calculation:
2400
g
s
o
r
b
i
t
o
l
+
2580
g
c
u
p
u
a
c
u
f
a
t
t
y
a
c
i
d
2400
g
s
o
r
b
i
t
o
l
+
2580
g
c
u
p
u
a
c
u
f
a
t
t
y
a
c
i
d
+
200
g
l
i
p
a
s
e
×
100
=
a
b
o
u
t
96
w
t
%
Before the effective filing date of the claimed invention, it would have been an obvious matter of routine optimization to have varied the total amount of the sorbitol and the oleic acid relative to the amount of the Novozym 435, including to amounts such that the sorbitol and the oleic acid make up about at least 95% by weight, based on the overall reaction mixture at the beginning of the esterification reaction when performing the method of Ducret, because the skilled artisan would have recognized that the amounts of the reactants (the sorbitol and oleic acid) relative to the biocatalyst (Novozyme 435) would have affected the extent of the esterification reaction and the esters of sorbitol obtained from the reaction. It is noted that “[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). Moreover, it would have been obvious to adjust the amount of the sorbitol and oleic acid to make up about 96% by weight, based on the overall reaction mixture at the beginning of the esterification reaction when performing the method of Ducret, because fatty esters were successfully obtained when sorbitol and fatty acids were reacted with Novozyme 435 at that weight percentage in the method of Teixeira Tage Biaggio. Therefore, instant claim 20 is rendered obvious.
Claims 21 and 22 are rejected under 35 U.S.C. 103 as being unpatentable over Ducret (as evidenced by Kennedy).
As discussed above, Ducret (as evidenced by Kennedy) anticipates claims 1-8, 16, 17, 19, and 23. Ducret differs from claim 21 in that Ducret does not expressly disclose that an average degree of esterification of any of their esters of sorbitol (directed to the claimed ‘sorbitol carboxylate’) is 1.1 to 4.0. Ducret differs from claim 22 in that Ducret does not expressly disclose that an average degree of esterification of any of their esters of sorbitol (directed to the claimed ‘sorbitol carboxylate’) is 2.6 to 4.0. For the purpose of applying prior art, the Examiner is interpreting ‘degree of esterification’ as being the number of ester groups in the sorbitol carboxylate.
However, Figure 1 of Ducret presents the results of the esterification between sorbitol and oleic acid in the solvent-free process (page 217, left column, third paragraph). Ducret states that this type of synthesis favors the formation of high esters of sorbitol, specifically mostly diesters but also triesters, tetraesters, etc. (page 217, left column, third paragraph). The formation of high esters of sorbitol renders obvious an average degree of esterification of sorbitol ester (i.e. sorbitol carboxylate) falling in the claimed ranges of 1.1 to 4.0 (instant claim 21) and 2.6 to 4.0 (instant claim 22) because most of the sorbitol esters have a degree of esterification of 2 (the diesters) and the other produced sorbitol esters have degrees of esterification greater than 2 (e.g. 3 for triesters, 4 for tetraesters, etc.) that at most can be 6 (number of hydroxyl groups in sorbitol). Therefore, instant claims 21 and 22 are rendered obvious.
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 1-8 and 16-23 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 8-13 and 17-19 of copending Application No. 18/570,018 in view of Johnson (International Journal of Toxicology. 2011. 30(Supplement 3): 228S-269S. Previously cited) and Gruning (US 6,320,065).
Claim 8 of `018 meets limitations of the claimed invention since it recites the embodiment of a process for enzymatic preparation of a mixture of n-nonanoic esters of sorbitol comprising A) providing sorbitol and at least one n-nonanoyl group donor, B) reacting sorbitol with the at least one n-nonanoyl group donor in the presence of a lipase at a temperature of 75ºC to 110ºC to give an n-nonanoic ester of sorbitol, and optionally C) purifying the n-nonanoic ester of sorbitol. Johnson teaches pelargonic acid, i.e. nonanoic acid, as a fatty acid (page 228S, first paragraph). The formula of pelargonic acid is shown in Figure 1 on page 233S of Johnson. In performing the method of claim 8 of `018, it would have been obvious to use pelargonic acid (i.e. nonanoic acid) as the ‘at least one n-nonanoyl group donor’ since it comprises an n-nonanoyl group and thus is directed to an n-nonanoyl group donor. As evident from the formula of pelargonic acid shown in Johnson, pelargonic acid is directed to an acyl group donor. Therefore, claim 8 of `018 in view of Johnson renders obvious a process meeting limitations of instant claim 1. Since claim 8 of `018 in view of Johnson reacts sorbitol with at least one acyl group donor in the presence of a lipase at the same temperature (compare B) of claim 8 of `018 with B) of instant claim 1), then the n-nonanoic ester of sorbitol prepared by the method of claim 8 of `018 in view of Johnson is a sorbitol carboxylate.
Though claim 8 of `018 does not recite blending the sorbitol with the at least one n-nonanoyl group donor, claim 9 of `018 recites that blending for at least ten minutes, thus meeting limitations of A) of instant claim 1 (the blending and its length of time). It would have been prima facie obvious to apply the limitation of claim 9 of `018 to claim 8 of `018 and its other dependent claims. Therefore, claim 8 of `018 incorporating claim 9 of `018 and in view of Johnson renders obvious a process meeting limitations of instant claim 1.
Claim 8 of `018 incorporating claim 9 of `018 and in view of Johnson differs from instant claim 1 in that there is no recitation of the blending of the sorbitol and the pelargonic acid (i.e. nonanoic acid) being within a temperature range of 90ºC to 120ºC. However, Gruning discloses a process for the preparation of fatty acid partial esters of polyols having at least 4 C atoms, at least one primary and at least one secondary alcohol group of the starting polyols, where in a first process step the polyols are reacted with a fatty acid or a fatty acid derivative to give a fatty acid partial ester, and in a second process step the fatty acid partial esters obtained are subjected to a selective enzymatic cleavage of primary ester groups (column 2, line 66 through column 3, line 8). Gruning points out that it is possible to carry out the process according to their invention entirely without solvent (column 3, lines 14-16). Sorbitol is a preferred polyol (column 3, lines 36-50, in particular lines 44 and 50). Also, a lipase can be used for performing the enzymatic cleaving, with the immobilized thermostable lipase Novozyme® 435 being particularly preferred (column 4, lines 54-65). The first stage (step) of the process is carried out at 110 to 300ºC for 2 to 12 hours (column 4, lines 21-29; claim 20 of Gruning). In the case of the reaction of sorbitol in the first stage of the process, the preferred temperature range is from 110 to 150ºC (column 4, lines 38-40).
It would have been obvious to the person of ordinary skill in the art to perform routine optimization of the temperature to 90ºC-120ºC or 100ºC-120ºC for conducting the blending of A) of claim 8 of `018 (incorporating claim 9 of `018) in view of Johnson, because the skilled artisan would have expected the temperature to be a results-effective parameter given that Gruning teaches that it affects the reaction of a polyol, e.g. sorbitol, with a fatty acid, and because Gruning taches that the preferred temperature for reacting sorbitol with a fatty acid prior to reaction with a lipase is 110 to 150ºC which overlaps with the claimed temperature ranges of 90ºC-120ºC or 100ºC-120ºC for step A). Therefore, claim 8 of `018 (incorporating claim 9 of `018) in view of Johnson and Gruning renders obvious instant claims 1, 16 (fatty acid), 17 (the temperature range of B) in claim 8 of `018 overlaps the claimed temperature range), and 18 (the length of time of at least ten minutes overlaps the claimed time period).
Regarding instant claims 2 and 19, as evident from the formula of pelargonic acid shown in Figure 1 of Johnson, pelargonic acid provides acyl groups that derive from a carboxylic acid containing 9 carbon atoms. Also, pelargonic acid is a natural fatty acid (see page 5, lines 5-8 of the instant specification). Thus, claim 8 of `018 (incorporating claim 9 of `018) in view of Johnson and Gruning renders obvious instant claims 2 and 19.
Regarding instant claims 3 and 20, claim 10 of `018 recites the embodiment in which the sorbitol with the at least one n-nonanoyl group donor accounts for at least 80% by weight, based on the overall reaction mixture at the start of B). Therefore, claim 10 of `018 (incorporating claim 9 of `018) in view of Johnson and Gruning renders obvious instant claims 3 and 20 (at least 80% by weight overlaps the claimed range).
Regarding instant claim 5, claim 11 of `018 meets the claimed limitation. Thus claim 11 of `018 (incorporating claim 9 of `018) in view of Johnson and Gruning renders obvious instant claim 5.
Regarding instant claim 6, claim 12 of `018 meets the claimed limitation. Thus claim 12 of `018 (incorporating claim 9 of `018) in view of Johnson and Gruning renders obvious instant claim 6.
Regarding instant claim 7, Gruning discloses that for the reaction of the enzyme catalyst (e.g. lipase) with the fatty acid partial esters obtained from reacting a polyol (e.g. sorbitol) with a fatty acid (see discussion above regarding the teachings of Gruning), the reaction time depends on the amount and the activity of the enzyme used and is, for example, up to 48 hours, preferably up to 24 hours (column 4, line 67 through column 5, line 3). Since the method rendered obvious by claim 8 of `018 (incorporating claim 9 of `018) in view of Johnson and Gruning involves the same reactants (sorbitol and a fatty acid) and enzyme catalyst (lipase) as Gruning, it would have been obvious to apply teachings of Gruning regarding the reaction of the enzyme catalyst, including the enzymatic reaction time of up to 48 hours, preferably up to 24 hours, to the invention of the claims of `018. Thus, step B) of claim 8 of `018 (incorporating claim 9 of `018) in view of Johnson and Gruning ends no later than 48 hours or no later than 24 hours after the lipase has been added, falling within the claimed range of ‘no later than 180 hours.’
Regarding instant claim 8, it would have been a matter of routine optimization to have varied the amount of the reactants (sorbitol and pelargonic acid) relative to each other because the skilled artisan would have recognized that their amounts relative to each other would have affected the n-nonanoic esters of sorbitol that are obtained through their reaction in the presence of a lipase when performing the method rendered by claim 8 of `018 (incorporating claim 9 of `018) in view of Johnson and Gruning; that is, the molar ratio of the sorbitol and the pelargonic acid would have been considered a results-effective parameter for optimization. In doing so, then the molar ratio of the sorbitol to all acyl groups present in the pelargonic acid (the claimed ‘at least one acyl group donor’) is optimizable to be within the claimed range of from 1.00:0.50 to 1.00:5.00. As such, claim 8 of `018 (incorporating claim 9 of `018) in view of Johnson and Gruning renders obvious instant claim 8.
Regarding instant claims 21 and 22, claim 17 of `018 recites that the average level of esterification of the mixture of n-nonanoic esters is 1.0 to 3.0. Claim 18 of `018 recites that the average level of esterification of the mixture of n-nonanoic esters is 1.1 to 2.7. Claim 19 of `018 recites that the average level of esterification of the mixture of n-nonanoic esters is 1.3 to 2.6. Each of the ranges of average level of esterification (directed to ‘average degree of esterification’) of claims 17-19 of `018 overlaps the ranges of average degree of esterification of instant claims 21 and 22. Since the process of claim 8 of `018 prepares the mixture of n-nonanoic esters of claim 1, then it would have been obvious to incorporate the limitations of claims 17-19 of `018 into the process of claim 8 of `018. Therefore, claim 8 of `018 (incorporating claim 9 of `018) in view of Johnson and Gruning and in further view of any one of claims 17-19 of `018 renders obvious instant claims 21 and 22.
Regarding instant claims 4 and 23, Gruning teaches that the process of their invention can be carried out entirely without solvent (column 3, lines 14-16). Since the method rendered obvious by claim 8 of `018 (incorporating claim 9 of `018) in view of Johnson and Gruning involves the same reactants (sorbitol and a fatty acid) and enzyme catalyst (lipase) as Gruning, it would have been obvious to apply teachings of Gruning to the invention of the claims of `018, including performing the method without solvent. Therefore, claim 8 of `018 (incorporating claim 9 of `018) in view of Johnson and Gruning renders obvious instant claim 23. Since water is a solvent, then this signifies that in B), a water content based on an overall reaction mixture is 0% by weight which falls in the range of ‘less than 15% by weight’ of instant claim 4. As such, claim 8 of `018 (incorporating claim 9 of `018) in view of Johnson and Gruning renders obvious instant claim 4.
This is a provisional nonstatutory double patenting rejection.
Response to Arguments
Applicant’s arguments, filed October 3, 2025, with respect to the rejection under 35 U.S.C. 103 of claims 1, 3-7, 16-18, and 20 as being unpatentable over Teixeira Tage Biaggio in view of Miyake and Gustini, and in light of Larsen; the rejection under 35 U.S.C. 103 of claims 2, 8, and 19 as being unpatentable over Teixeira Tage Biaggio, Miyake, Gustini, and Larsen in further view of Gomes and in light of Buckley; the rejection under 35 U.S.C. 103 of claims 21 and 22 as being unpatentable over Teixeira Tage Biaggio, Miyake, Gustini, Larsen, Gomes, and Buckley in further view of Ducret; and the nonstatutory double patenting rejection of claims 1-3, 5, 6, and 16-22 as being unpatentable over claims 8-13 and 17-19 of copending Application No. 18/570,018 in view of Johnson and Miyake, have been fully considered and are persuasive. In particular, Applicant’s arguments are persuasive with respect to applying Miyake to the invention of Teixeira Tage Biaggio and the claims of copending Application No. 18/570,018 – see Applicant’s arguments regarding Miyake on pages 8-10. Therefore, these rejections have been withdrawn.
However, upon further consideration, a new ground(s) of rejection is made in view of Ducret (cited in new rejections under 35 U.S.C. 102 and 35 U.S.C. 103) and Gruning (cited as a secondary reference for a nonstatutory double patenting rejection over copending Application No. 18/570,018). Also, upon further consideration, a new ground of rejection is made under 35 U.S.C. 112(b) over claims 21 and 22.
To the extent Applicant’s arguments are directed to the nonstatutory double patenting rejection over copending Application No. 18/570,018 (modified above in view of Johnson and Gruning), they are unpersuasive. Applicant argues that it would not have been obvious to blend sorbitol and acyl donor for at least 10 minutes, since there is no suggestion to delay reaction following blending. However, claim 9 of `018 recites step A) comprising blending sorbitol with the at least one n-nonanoyl group donor for at least ten minutes before step B) of reacting the two. Claim 9 of `018 in view of Johnson (which teaches pelargonic acid, i.e. nonanoic acid, as a fatty acid) renders obvious the at least one n-nonanoyl group donor being directed to an acyl group donor. Furthermore, Applicant argues that since claim 8 of `018 reacts a mixture of xylitol, sorbitol, and erythritol in the preparation of a mixture of n-nonanoic esters, it would not have been obvious to have blended sorbitol and an acyl donor prior to reaction in the presence of a lipase. However, claim 8 of `018 recites preparation of “a mixture of n-nonanoic esters of xylitol, sorbitol or erythritol” (lines 1-2), providing and reacting “xylitol, sorbitol or erythritol” (steps A) and B)), and purifying the n-nonanoic ester of “xylitol, sorbitol or erythritol” (step C)), thus not requiring a mixture of all three of xylitol, sorbitol, and erythritol in performing the steps. As such, claim 8 of `018 includes the embodiment of only providing and reacting (in the presence of a lipase) sorbitol with at least one n-nonanoyl group donor, and purifying only the n-nonanoic ester of sorbitol.
Regarding the objection to the specification, Applicant points out that the amendment of March 12, 2025, amended line 1 to recite “www.gog.com” which is not a URL as it lacks the scheme “https://” associated with a URL. Therefore, Applicant argues that no further correction is necessary. However, see the second paragraph of the objection and MPEP 608.01(VII). Though “www.gog.com” does not include the prefix http://, it is directed to browser-executable code that becomes a live web link.
Conclusion
No claims are allowed.
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Sef
/SUSAN E. FERNANDEZ/ Examiner, Art Unit 1651