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 .
Election/Restrictions
Claims 14-15 remain withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim. Applicant timely traversed the restriction (election) requirement in the reply filed on 06/10/2025.
Claims 1-3, 5-13 and 16-17, and 19-20 are directed to the elected invention and have been examined on their merits.
Amendments
Claim 1 now requires the mixture to further comprise at least one substance selected from the group consisting of a choline salt, an ammonium salt, and a phosphonium salt, in an amount 0% to less than 2% by weight, where a weight percentage relates to all of the at least two compounds in the mixture.
Claims 2-3, 5-13, 16-17, and 19-20 have had minor typographic changes.
Claim 14 is withdrawn and has had minor typographic changes.
Claims 4 and 18 are canceled.
Specification
Previous objection to the specification
The specification was objected to because it contained the use of trade names or marks used in commerce without generic terminology or the proper symbols indicating use in commerce.
Applicant has argued that “each of the commercial enzymes disclosed on page 10 provide the name of the supplier, such that one of ordinary skill in the art would be able [to] identify the product with the supplies, the foundational purpose of trademark law” (Remarks, p. 11).
Although it is recognized that the source of goods is appropriately identified. The purpose of the requirement is also so that the specification clearly defines the actual goods being referenced. For example, “Novoyzme 435” is a trade name assigned by the manufacturer. The manufacturer may change the formulation of Novozyme 435. Therefore, it is important that the terms are accompanied by generic terminology. Moreover, terms such as “Lipozyme” are registered trademarks (Serial No. 73647944). Accordingly, they should be accompanied by the registered trademark symbol.
Because Applicant has not made the appropriate correction, the objection is maintained.
Maintained objection to the specification
The use of the terms “Lipozyme”, “Novozym”, “Chirazyme”, “Amano”, and “Purolite” are noted in p. 10 of the specification. These are trade names or a marks used in commerce and should be accompanied by the generic terminology; furthermore, the terms should be capitalized wherever they appear 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.
Appropriate correction is required.
Claim Objections
Previous objections to the claims
The claims were previously objected to because of the references to step “B)” and for minor informalities. Applicant has removed all such references and the objection is therefore withdrawn.
Claim Interpretation
The claims are directed to a process involving enzymatic preparation of “a mixture composition comprising at least two selected from the group consisting of a sugar ester and a sugar alcohol ester”. Applicant has provided a special definition for the phrase “two selected from sugar esters and/or sugar alcohol esters” which “should be understood to mean that the two esters differ in terms of their sugars and/or in terms of their sugar alcohols” and “esters must therefore be present which have two different residues in terms of sugar and/or sugar alcohol residue” (Specification, p. 6, lines 33-36).
Accordingly, the phrase “at least two selected from the group consisting of a sugar ester and a sugar alcohol ester” is interpreted to simply mean that there are two esters which differ in their sugar or sugar alcohol residue. In other words, the claim does not require preparation of both a sugar ester and a sugar alcohol ester but merely requires at least two compositions which are either sugar esters or sugar alcohol esters.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Previous rejection under 35 U.S.C. § 112(d)
RE: Rejection of claim 18 under 35 U.S.C. 112(d), as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Claim 18 was rejected because it excluded limitations which were previously set forth. Specifically, it recited the limitation “wherein the mixture in B) does not comprise the at least one substance”. Applicant has canceled this claim, rendering the rejection moot.
New grounds of rejection under 35 U.S.C. § 112(b)
Claims 1-3, 5-13, 16-17, and 19-20 are rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor, regards as the invention.
Claim 1 has been amended to require at least one substance selected from the group consisting of a choline salt, an ammonium salt, and a phosphonium salt, in an amount 0% to less than 2% by weight, where a weight percentage relates to all of the at least two compounds in the mixture.
Claim 1 lacks clarity because it simultaneously requires “at least one substance” but also allows for said substance to be in an amount of 0% by weight. Thus, it is not clear whether the at least one substance is actually required to be included in the mixture. For example, a mixture containing the at least two compounds and “at least one substance” in an amount of 0% by weight is indistinguishable from the same composition not comprising the substance at all.
In the interest of compact prosecution, the claims have been examined for prior art purposes as if the mixture must contain some amount of the “at least one substance” in an amount of less than 2% by weight.
Claims 2-3, 5-13, 16-17, and 19-20 are rejected because they depend from claim 1 and do not further clarify the metes and bounds of the independent claim.
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.
Previous rejection under 35 U.S.C. § 102
RE: Rejection of claims 1-3, 7-8, 11, and 16 under 35 U.S.C. 102(a)(1) as being anticipated by Siebenhaller et al. (Bioresources and Bioprocessing, 2017, Vol. 4(25), pages 1-9).
Applicant asserts that the amended claims are not anticipated or obvious over the cited prior art because Siebenhaller describes choline salt acting as a functional component in a deep eutectic solvent and because it is a functional component, it would have not been obvious to have arrived at a method wherein the choline salt is less than 2% by weight. Specifically, applicant argues the following.
First, applicant asserts that the choline salt is described to be in an intentional formulation as a functional component and therefore using less than 2 wt. % would not have been obvious because there is no suggestion to reduce the content of a choline salt.
Second, applicant asserts that this concentration could not have been arrived at through routine optimization because the particular parameter (in this case, choline salt concentration) was not known to be a result effective variable and there would have therefore not been motivation to have changed the choline salt content.
Third, applicant asserts that because choline salt is a component of a deep eutectic mixture, which has a unique thermal behavior, there would have been no motivation to have adjusted the choline salt content because the behavior as a eutectic mixture is not assured at all concentrations. Applicant supports this argument by stating that it would not be unreasonable to conclude that choline salt contributes to the melting point reduction in the formation of a DES such that the eutectic mixture behaves as a liquid solvent instead of a solid.
Applicant’s arguments have been fully considered but are not sufficient to overcome the rejection of record for the following reasons.
With respect to the first argument, the “routine optimization” rationale is based upon the finding that a person having ordinary skill in the art would have been motivated to experiment with various conditions (in this case, the concentration of choline salt) in order to optimize Siebenhaller’s process. It has been asserted in the rejection of record that a person having ordinary skill in the art would have routinely experimented with various reaction conditions in light of Siebenhaller’s direct teaching that “this is a non-optimized synthesis setup” (p. 6, right col., par. 1). Accordingly, although it is acknowledged that Siebenhaller employs a concentration higher than what is instantly claimed, a person having ordinary skill in the art would not have taken Siebenhaller’s reaction conditions as being the only possible reaction conditions (i.e., would not conclude that choline salt must be present in an amount of 43.48 wt. %).
With respect to the second argument, although it is noted that Siebenhaller calls out by name various parameters which can be altered, in the prior paragraph it also teaches that “[d]epending on the solvent, enzyme, substrates and time…it is possible to convert 100% of the sugar to a glycolipid” (p. 6, right col., par. 1). This alone is sufficient motivation to alter the solvent concentration in order to optimize conversion of sugars to glycolipids.
And to the extent that Siebenhaller does call out particular parameters, it includes optimizations such as altering “water content” (Siebenhaller, p. 6, right col., par. 2) while also teaching a preference for a “nearly water-free environment” (p. 2, left col., par. 2). Thus, even though Siebenhaller prefers a “nearly water-free environment”, it also acknowledges that “[i]t has already been shown that enzymatic reactions can be accelerated by increasing the water content of the DES” (p. 6, right col., par. 2). Similarly, although Siebenhaller may teach the use of a specific concentration of choline salt, that does not preclude optimizations such as by altering the amount of choline salt.
With respect to the third argument, for the reasons discussed above, it would have been obvious to have routinely experimented with various concentrations of choline salt. It is noted that applicant’s claim does not require any particular temperature (claim 8 allows for a range of between 20°C and 160°C). Accordingly, even if the choline salt is not present in the mixture at a concentration sufficient to lower the melting point, a person having ordinary skill in the art could easily have altered the temperature to ensure that the mixture is in a liquid state. Additionally, the claims are not particularly limited to components having similar melting points and therefore the melting point reducing property of DES may not necessarily be relevant to the process of merely reacting a mixture containing at least two compounds selected from the group consisting of a sugar and a sugar alcohol, with at least one acyl group donor, in the presence of a lipase.
In summary, applicant’s claims differ from the prior art only in the concentration of choline salt. Siebenhaller’s disclosure makes clear that the process of reacting a mixture choline salt and containing at least two compounds in the presence of a lipase is a non-optimized process. Accordingly, there was ample suggestion to a person having ordinary skill in the art to optimize Siebenhaller’s methods such as by experimenting with reduced concentrations of choline salts. And although applicant’s specification prophetically discusses processes wherein the reaction mixture comprises substances including choline salts “in an amount of less than 2% by weight” (p. 9, lines 19-25; emphasis added), none of the working examples appear to actually use reaction mixtures comprising choline salts (or any of the other recited salts) in an amount of less than 2% by weight. Accordingly, there is no evidence of record that the recited range elicits an unexpected or remarkable result or is critical to the claimed process. It is noted that a composition “further comprising at least one substance…in an amount 0% to less than 2% by weight” is different from a composition which “does not comprise” the at least one substance. In other words, in order to meet the claim to the negative limitation, there must be a motivation to remove Siebenhaller’s choline salt (a point which is not argued herein) but in order to meet a claim in which the choline salt merely differs in concentration, there must only be motivation to routinely optimize the process; which there is.
For at least these reasons, the rejection of record must be maintained. In order to address applicant’s amendments to claim 1, the rejection of record under 35 U.S.C. § 102 has been withdrawn and a new ground of rejection under 35 U.S.C. § 103 is set forth below.
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.
Previous rejections under 35 U.S.C. § 103
Response to applicant’s arguments
As discussed above, amended claim 1 is obvious over the teachings of Siebenhaller. Accordingly, new grounds of rejection are made below over the amended claims.
New grounds of rejection under 35 U.S.C. § 103
Claims 1-3, 7-9, 11-13, and 16 are rejected under 35 U.S.C. 103 as being unpatentable over Siebenhaller et al. (Bioresources and Bioprocessing, 2017, Vol. 4(25), pages 1-9).
Siebenhaller teaches that the emulsifying properties and foaming ability of glycolipids enable their application in cosmetics, pharmaceuticals, or the food industry (p. 2, left col., par. 1). Moreover, glycolipids are very mild biocompatible agents which are skin-friendly, making them particularly suitable for the use in cosmetics and many glycolipids suppress bacterial growth, so there are still several additional application possibilities (Id.). Siebenhaller teaches that the enzymatic synthesis of sugar esters can be performed using a lipase in a nearly water-free environment (p. 2, left col., par. 2). Under these conditions, lipases reverse their hydrolytic activity and form ester bonds between a hydroxyl group of a sugar and the carboxyl group of a fatty acid (Id.). Siebenhaller explains that in order to avoid problems of low sugar solubility, deep eutectic solvents (DESs) can be used (Id.).
Regarding claim 1, Siebenhaller teaches a synthesis reaction performed by adding 100 mg of lipase (Novozym® 435) and 1.5 mmol of fatty acid (vinyl-octanoate or octanoic acid; i.e., at least one acyl group donor) to 3.5 ml of “the formed DES” (p. 3, left col., par. 4). Siebenhaller teaches that the reaction yielded glucose-octanoate and xylose-octanoate (i.e., at least two selected from the group consisting of a sugar ester and a sugar alcohol ester)(p. 5, right col., par. 3-5; p. 6, left col., Tables 2-3).
Accordingly, Siebenhaller teaches the claimed process for the enzymatic preparation of a mixture composition comprising at least two selected from the group consisting of a sugar ester and a sugar alcohol ester.
With respect to the new limitation that the mixture further comprises at least one substance selected from the group consisting of a choline salt, an ammonium salt, and a phosphonium salt, in an amount 0% to less than 2% by weight, where a weight percentage relates to all of the at least two compounds in the mixture, Siebenhaller teaches that the mixture comprises a DES, which is made up of choline chloride (i.e., a choline salt)(p. 3, left col., par. 3). Siebenhaller teaches that each 3.5 ml DES solution contains 1.81 grams glucose and 0.42 grams xylose (p. 4, right col., par. 3). Siebenhaller further teaches that the choline chloride was mixed with the dried sugar mix in a weight ratio of 1:1.3 (w/w).
Thus, Siebenhaller teaches the choline salt in an amount of 43.48% (
1
2.3
×
100
)
and the sugars were in an amount of 56.52% (
1.3
2.3
×
100
)
.
Accordingly, Siebenhaller teaches the choline salt but does not teach a choline salt in an amount of less than 2% by weight where a weight percentage relates to all of the at least two compounds in the mixture.
Nonetheless, it would have been obvious to have routinely experimented with various concentrations of the choline salt to arrive at a concentration of less than 2% by weight. Siebenhaller suggests performing this routine optimization by teaching that the reported process is a “non-optimized synthesis” and the achieved yields are low (p. 6, right col., par. 1). Thus, to achieve higher yields, the process can be improved by optimizing various parameters (p. 6, right col., par. 2). Accordingly, a person having ordinary skill in the art could have experimented with various relative concentrations of the choline salt to the “at least two compounds” and would have been expected to arrive at the claimed range of “less than 2%” with a reasonable expectation of success. The expectation of success is reasonable because the process merely requires the production of the esters and this would have been expected to occur irrespective of the choline salt concentration because the reaction is between the sugars, the acyl groups, and the lipase enzyme and the choline salts merely serve to improve the solubilities of the sugars in the nearly water-free reaction. There is no evidence of record that the claimed range elicits some remarkable or unexpected result (such as improvement of Siebenhaller’s process). Generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical (MPEP § 2144.05(II)(A)).
Thus, claim 1 is obvious over Siebenhaller as a result of routine experimentation.
Regarding claim 2, Siebenhaller teaches the use of glucose and xylose (p. 4, right col., par. 3).
Regarding claim 3, Siebenhaller teaches the use of the fatty acids vinyl-octanoate and octanoic acid (p. 3, left col., par. 4).
Regarding claim 7, Siebenhaller teaches the use of lipase B from Candida antarctica (p. 2, right col., par. 2).
Regarding claim 8, Siebenhaller teaches that the reaction was performed for 72 hours at 50 °C (p. 3, left col., par. 4). This value falls within the recited range of a reaction temperature in a range between 20 °C and 160 °C. "If the prior art discloses a point within the claimed range, the prior art anticipates the claim." UCB, Inc. v. Actavis Labs. UT, Inc., 65 F.4th 679, 687, 2023 USPQ2d 448 (Fed. Cir. 2023)(MPEP § 2131.03(I)).
Regarding claim 9, as discussed above, Siebenhaller renders obvious the process of claim 1. Siebenhaller further teaches that the transesterification with vinyl-octanoate normally creates ethenol, which tautomerizes to acetaldehyde and the reaction is pushed forward due to the high volatility of the acetaldehyde by-product (p. 5, left col., par. 2). However, under nearly water-free conditions (required to reverse the lipase activity, as discussed above), the reaction can result in the formation of sugar aldehydes if the acetaldehyde does not evaporate fast enough (Id.). Accordingly, Siebenhaller suggests a synthesis reaction under reduced pressure as a possible option to increase acetaldehyde evaporation (Id.).
Accordingly, because Siebenhaller teaches a “non-optimized synthesis”, teaches that the yields can be improved through optimization, and because Siebenhaller suggests a synthesis reaction under a reduced pressure to increase acetaldehyde evaporation (and therefore move the reaction forward)(p. 5, left col., par. 2; p. 6, right col., par. 1), it would have been obvious to have modified Siebenhaller’s method such that it occurs under “reduced pressure”. There would have been a reasonable expectation of success because Siebenhaller teaches that this would be expected to improve the yield by removing the byproducts (and thus moving the reaction forward). This obviousness is based upon the “Some Teachings, Suggestion, or Motivation in the Prior Art That Would Have Led One of Ordinary Skill To Modify the Prior Art Reference or To Combine Prior Art Reference Teachings To Arrive at the Claimed Invention” rationale set forth in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007). See MPEP 2143(I)(G).
And although Siebenhaller does not suggest any particular pressures for this process, it would have been obvious to have routinely experimented with various “reduced pressures” and persons having ordinary skill in the art could have arrived at a pressure range of less than 1 bar with a reasonable expectation of success because this wide range encompasses almost all reduced pressures under atmospheric pressure.
Thus, claim 9 is obvious over Siebenhaller as a result of routine experimentation.
Regarding claim 11, Siebenhaller further teaches that the transesterification with vinyl-octanoate normally creates ethenol, which tautomerizes to acetaldehyde and the reaction is pushed forwards due to the high volatility of the acetaldehyde by-product (p. 5, left col., par. 2; p. 6, Fig. 2). Additionally, it is noted that Siebenhaller teaches a step of glycolipid extraction with ethyl acetate (p. 3, left col., par. 5) and a purification and fractionation step using flash chromatography to separate the glucose- and xylose-octanoates (p. 3, right col., par. 2). Accordingly, Siebenhaller teaches the process wherein the byproducts formed in step B) are removed.
Regarding claim 12, Siebenhaller teaches a step before the reaction step involving obtaining a monosaccharide solution from beechwood fractionation via an acid-catalyzed oranosolv process (p. 2, right col., par. 3). The enzymatic hydrolysis of the beechwood fiber resulted in a mixture containing cellobiose, xylose, and glucose, which were subsequently purified through a pretreatment step and spray dried to result in the saccharide mixture (p. 2, right col., par. 3 through p. 3, left col., par. 2).
Thus, Siebenhaller’s method does not involve a step of providing the at least two compounds (in this case, glucose and xylose) spatially separately from each other in a solid form or in a form dissolved in water and mixing the at least two compounds to give the mixture in step B).
Nonetheless, it would have been obvious to have modified Siebenhaller’s method such that the “at least two compounds” (glucose and xylose) are provided spatially separately in a solid form or in a form dissolved in water and mixed to give the mixture containing both components. The proposed modification merely changes the preparation of the mixture used in Siebenhaller’s process. It would have been obvious to have provided the two sugars separately and combined them to simplify the process, improve the reactant purity, and/or reduce the cost of Siebenhaller’s process. The modification could be achieved by purchasing (or otherwise procuring) glucose and xylose (i.e., providing them spatially separately) and then mixing them to form the mixture rather than performing the multi-step and multi-hour process described by Siebenhaller (obtaining a beechwood fiber, performing enzymatic hydrolysis, purifying the hydrolysate to remove phenolic or lignin compounds, using activated carbon, rigorous shaking, 3 hour incubation, and purification with two-step filtration, followed by spray drying) to derive the sugars from beechwood (p. 2, right col., par. 3 through p. 3, left col., par. 1). There would have been a reasonable expectation of success because the proposed modification merely changes the source of the glucose and xylose mixture and the extra-solution modification to merely change the source would not be expected to fundamentally alter the process described by Siebenhaller. This obviousness is based upon the “Some Teaching, Suggestion, or Motivation in the Prior Art That Would Have Led One of Ordinary Skill To Modify the Prior Art Reference or To Combine Prior Art Reference Teachings To Arrive at the Claimed Invention” rationale set forth in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007). See MPEP 2143(I)(G).
Regarding claim 13, as discussed above, Siebenhaller makes obvious providing the at least two compounds spatially separately from each other. Siebenhaller further teaches that the DES solution to which the reactants were added had a water content of 5.4% (p. 4, right col., par. 4; p. 5, left col., par. 2). This percentage is considered to be less than 17% by weight, where a weight percentage relates to a total amount of the mixture because although this percentage reported by Siebenhaller is the weight percentage in the DES solution, adding the lipase and fatty acid to the DES mixture would reduce the total amount of water by weight from the initial value of 5.4% in the DES mixture. As such, it is readily apparent that Siebenhaller’s reaction must use less than 17% by weight of water. Indeed, it would have been obvious to have used a lower percentage of water because Siebenhaller teaches that the reaction should occur in nearly water-free environments (p. 2, left col., par. 2).
Thus, claim 13 is obvious over Siebenhaller.
Regarding claim 16, as discussed above in the rejection of claims 1 and 3, Siebenhaller teaches the use of the fatty acids vinyl-octanoate and octanoic acid as the at least one acyl group donor (p. 3, left col., par. 4). As such, Siebenhaller teaches both a fatty acid (octanoic acid) and a fatty acid ester (vinyl-octanoate).
Claims 1-3, 5-9, 11-13, and 16 are rejected under 35 U.S.C. 103 as being unpatentable over Siebenhaller et al. (Bioresources and Bioprocessing, 2017, Vol. 4(25), pages 1-9), as evidenced by PubChem 1 (D-Glucose, https://pubchem.ncbi.nlm.nih.gov/compound/D-Glucose, webpage, accessed July 2025) and PubChem 2 (D-Xylose, https://pubchem.ncbi.nlm.nih.gov/compound/D-Xylose, webpage, accessed July 2025).
The teachings of Siebenhaller are set forth above and applied herein. Siebenhaller renders obvious claims 1-3, 7-9, 11-13, and 16.
Regarding claim 5, Siebenhaller teaches that each 3.5 ml DES solution contains 1.81 grams glucose and 0.42 grams xylose (p. 4, right col., par. 3). To this, 1.5 mmol of the fatty acid was added (p. 3, left col., par. 4).
PubChem 1 provides evidence that the molar weight of glucose is 180.16 g/mol. PubChem 2 provides evidence that the molar weight of xylose is 150.13 g/mol. Siebenhaller demonstrates that the fatty acids have one acyl group (p. 6, Fig. 2).
Accordingly, Siebenhaller’s mixture contains:
0.01005 mol glucose (
1.81
g
180.16
g
/
m
o
l
);
0.00280 mol xylose (
0.42
g
150.13
g
/
m
o
l
);
0.0015 mol vinyl-octanoate or octanoate.
This adds to 0.01285 mol (0.01005 mol + 0.00280 mol) of all the at least two compounds and 0.0015 mol of all acyl groups present in the at least one acyl group donor, which becomes a ratio of 8.57 : 1 or 1 : 0.117. This is a value falling within the claimed range of from 1.00 : 0.08 to 1.00 : 10.00. "If the prior art discloses a point within the claimed range, the prior art anticipates the claim." UCB, Inc. v. Actavis Labs. UT, Inc., 65 F.4th 679, 687, 2023 USPQ2d 448 (Fed. Cir. 2023)(MPEP § 2131.03(I)).
Thus, Siebenhaller, as evidenced by PubChem 1 and PubChem 2, renders obvious claim 5.
Regarding claim 6, as discussed above, Siebenhaller renders obvious the process of claim 1. The instant claim limits the molar ratio of “all primary hydroxyl groups in all the at least two compounds” to “all acyl groups present in the at least one acyl group donors”.
Siebenhaller teaches that each 3.5 ml DES solution contains 1.81 grams glucose and 0.42 grams xylose (p. 4, right col., par. 3). To this, 1.5 mmol of the fatty acid was added (p. 3, left col., par. 4).
PubChem 1 provides evidence that the molar weight of glucose is 180.16 g/mol and that glucose contains one primary hydroxyl group (as seen on C6). PubChem 2 provides evidence that the molar weight of xylose is 150.13 g/mol and that xylose contains one primary hydroxyl group (as seen on C5). Siebenhaller demonstrates that the fatty acids have one acyl group (p. 6, Fig. 2).
Accordingly, Siebenhaller’s mixture contains:
0.01005 mol glucose (
1.81
g
180.16
g
/
m
o
l
);
0.00280 mol xylose (
0.42
g
150.13
g
/
m
o
l
);
0.0015 mol vinyl-octanoate or octanoate.
This adds to 0.01285 mol (0.01005 mol + 0.00280 mol) of primary hydroxyl groups and 0.0015 mol of acyl groups, which becomes a ratio of 8.57 : 1 or 1 : 0.117. This is a value falling within the claimed range of from 1.00 : 0.08 to 1.00 : 10.00. "If the prior art discloses a point within the claimed range, the prior art anticipates the claim." UCB, Inc. v. Actavis Labs. UT, Inc., 65 F.4th 679, 687, 2023 USPQ2d 448 (Fed. Cir. 2023)(MPEP § 2131.03(I)).
Thus, Siebenhaller, as evidenced by PubChem 1 and PubChem 2, renders obvious claim 6.
Claims 1-3, 7-13, 16-17, and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Siebenhaller et al. (Bioresources and Bioprocessing, 2017, Vol. 4(25), pages 1-9), as evidenced by PubChem 3 (Vinyl octanoate, https://pubchem.ncbi.nlm.nih.gov/compound/Vinyl-octanoate, webpage, accessed July 2025) and PubChem 4 (Octanoate, https://pubchem.ncbi.nlm.nih.gov/compound/Octanoate, webpage, accessed July 2025).
The teachings of Siebenhaller are set forth above and applied herein. Siebenhaller renders obvious claims 1-3, 7-9, 11-13, and 16.
Regarding claim 10, Siebenhaller teaches that each reaction contains:
1.81 grams glucose (p. 4, right col., par. 3);
0.42 grams xylose (Id.);
0.1 grams lipase (p. 3, left col., par. 4);
0.26 grams vinyl-octanoate or 0.22 grams octanoate (derived from 1.5 mmol; p. 3, left col., par. 4)
PubChem 3 and 4 provide evidence that vinyl-octanoate and octanoate have a molar weight of 170.25 g/mol and 143.20 g/mol, respectively;
1.72 grams choline chloride (derived from the 1:1.3 (w/w) formulation in p. 3, left col., par. 3).
Thus, the total reaction weight is 4.31 grams with vinyl-octanoate and 4.27 grams with octanoate and Siebenhaller therefore teaches that the mixture and the at least one acyl group donor make up 57.8% (2.49/4.31) and 57.4% (2.45/4.27), depending on the acyl donor. Both of these amounts fall well-within the claimed range of at least 10% by weight. "If the prior art discloses a point within the claimed range, the prior art anticipates the claim." UCB, Inc. v. Actavis Labs. UT, Inc., 65 F.4th 679, 687, 2023 USPQ2d 448 (Fed. Cir. 2023)(MPEP § 2131.03(I)).
Regarding claim 17, as discussed above, Siebenhaller renders obvious the process of claim 3 including the use of vinyl-octanoate and octanoate. PubChem 3 and 4 provide evidence that vinyl-octanoate and octanoate are also known as caprylic acid, vinyl ester and caprylate, respectively. Thus, both compositions provide an acyl group of caprylic acid.
Regarding claim 20, as discussed above, Siebenhaller, as evidenced by PubChem 3 and 4, renders obvious the process wherein the mixture and the at least one acyl group donor make up 57.8% (2.49/4.31) and 57.4% (2.45/4.27).
Siebenhaller does not teach the method wherein the mixture and the at least one acyl group donor make up in total at least 90% by weight of the overall reaction mixture.
Nonetheless, it would have been obvious to have routinely experimented with higher weight percentages of the reactants in order to optimize Siebenhaller’s process. Siebenhaller suggests performing this optimization by teaching that the reported process is a “non-optimized synthesis”, and the achieved yields are low (p. 6, right col., par. 1). Thus, to achieve higher yields, the process can be improved by optimizing various parameters (p. 6, right col., par. 2). Accordingly, a person having ordinary skill in the art could have experimented with higher weight percentages of the reactants and would have been expected to arrive at the claimed weight percentage of “at least 90%” with a reasonable expectation of success. The expectation of success is reasonable because the process merely requires the production of the esters and this would have been expected to occur irrespective of the relative amounts of the two reactants. Moreover, increasing the amount of reactants while keeping the weight of the solvent and lipase would have been expected to improve the enzyme saturation and thus improve the yield. There is no evidence of record that the claimed range (“at least 90%”) elicits some remarkable or unexpected effect. Generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical (MPEP § 2144.05(II)(A)).
Thus, claim 20 is obvious over Siebenhaller, as evidenced by PubChem 3 and 4, as a result of routine experimentation.
Claims 1-3, 7-9, 11-13, 16, and 18 are rejected under 35 U.S.C. 103 as being unpatentable over Siebenhaller et al. (Bioresources and Bioprocessing, 2017, Vol. 4(25), pages 1-9) in view of Elgharbawy et al. (Journal of Molecular Liquids, 2018, Vol. 251, pages 150-166).
The teachings of Siebenhaller are set forth above and applied herein. Siebenhaller is found to render obvious claims 1-3, 7-9, 11-13, and 16.
Regarding claim 18, as discussed in the rejection under 35 U.S.C. § 112(d), the instant claim does not further limit claim 4 because it removes a component (“at least one substance”) which was added by claim 4. Therefore, the claim broadens, rather than narrows the scope of claim 4 because it does not require all of the components of claim 4.
Nonetheless, in the interest of compact prosecution, it is noted that it would have been obvious to have arrived at a method which does not contain “at least one substance selected from the group consisting of a choline salt, an ammonium salt, and a phosphonium salt”.
Elgharbawy et al. (hereinafter Elgharbawy) teaches that enzyme-catalysed reactions have emerged as competitive and economical alternative to classical synthetic approaches (p. 151, left col., par. 1). Considering the need for environmentally friendly, low-toxicity, safe, and low-volatility organic solvents, ionic liquids (ILs) have been introduced and appear to be competing as substitutes and as environmentally attractive alternatives because of their peculiar physical and chemical properties (Id.). ILs are composed of imidazolium, pyridinium, pyrrolidinium, ammonium, cholinium, morpholinium, and phosphonium derivatives, along with organic or inorganic anions (p. 151, left col., par. 2). Elgharbawy teaches that the ionic liquid C7MIM was able to substitute n-heptane in an enzymatic reaction with Candida antarctica lipase B and the IL stabilized the lipase enzyme (p. 151, right col., par. 1). Elgharbawy further teaches that lipases have been broadly used with ILs and demonstrate enhance stability in ILs when compared to traditional solvents including an apparent stimulation of enzyme activity (p. 152, left col., par. 2). Elgharbawy summarizes the advantages of ILs as encompassing a low melting point, negligible vapor pressure, high thermal stability, adjustable physical and chemical properties, water-immiscibility, wide solvent activity, positive effects on enzymes, and recyclability and reusability (p. 152, right col., Table 1). Elgharbawy provides a summary of various lipase-catalysed syntheses of esters from an acyl donor and an acyl acceptor (p. 161, Table 3). The ILs taught by Elgharbawy to be useful for lipase-mediated transesterification include [2PentMIM][BF4], [sBMIM][BF], [BMIM][PF6], [EMIM][BF4], [BMIM][BF4] (with and without DMSO), [OMIM][BF4], [EMIM][PF6], [OMIM][PF6], [BMIM][NTf2], and [C16TMA][Ntf2](Id.).
Thus, since Siebenhaller suggests improving the process by describing its method as a “non-optimized synthesis” with low yields (p. 6, right col., par. 1). It would have been obvious to have substituted the choline salt in Siebenhaller’s methods with one of the many suitable ionic liquids taught by Elgharbawy (i.e., not a choline salt, an ammonium salt, and a phosphonium salt). Both the choline salt and the ionic liquids functions were known in the art previously (i.e., they were both known to be suitable solvents for lipase-mediated esterification reactions). The result of the substitution would have been predictable because Elgharbawy provides a litany of reactions (Table 3) wherein ionic liquids were used successfully with lipases for esterification of sugars and sugar alcohols. Furthermore, there would have been a particular motivation to make this substitution because Elgharbawy teaches many advantages to ionic liquids including their low melting point, negligible vapor pressure, high thermal stability, adjustable physical and chemical properties, water-immiscibility, wide solvent activity, positive effects on enzymes (including stimulation of lipases), and recyclability and reusability (p. 152, right col., Table 1). This obviousness is based upon the “Simple Substitution of One Known Element for Another to Obtain Predictable Results” rationale set forth in in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007).
Thus, after making the substitution made obvious by Siebenhaller in view of Elgharbawy, the process would not comprise the substances set forth in claim 4 because the substance in claim 4 would have been substituted with one of Elgharbawy’s ionic liquids.
Claims 1-3, 5-9, 11-13, 16, and 19 are rejected under 35 U.S.C. 103 as being unpatentable over Siebenhaller et al. (Bioresources and Bioprocessing, 2017, Vol. 4(25), pages 1-9), as evidenced by PubChem 1 (D-Glucose, https://pubchem.ncbi.nlm.nih.gov/compound/D-Glucose, webpage, accessed July 2025) and PubChem 2 (D-Xylose, https://pubchem.ncbi.nlm.nih.gov/compound/D-Xylose, webpage, accessed July 2025), and in view of Gumel et al. (Process Biochemistry, 2011, Vol. 46, pages 2079-2090).
The teachings of Siebenhaller, PubChem 1, and PubChem 2 are set forth above and applied herein. Siebenhaller, as evidenced by PubChem 1 and PubChem 2, is found to render obvious claims 1-3, 5-9, 11-13, and 16.
Regarding claim 19, as discussed above, Siebenhaller, as evidenced by PubChem 1 and 2, renders obvious the claimed ratio range set forth in claim 5.
Specifically, Siebenhaller teaches a ratio of 1 : 0.117. Siebenhaller does not teach a ratio range of 1.00 : 2.00 to 1.00 : 4.50.
Nonetheless, it would have been obvious to have routinely experimented with relative proportions of the “at least two compounds” to the “acyl groups” in order to optimize Siebenhaller’s process. Siebenhaller suggests performing this optimization by teaching that the reported process is a “non-optimized synthesis”, and the achieved yields are low (p. 6, right col., par. 1). Thus, to achieve higher yields, the process can be improved by optimizing various parameters (p. 6, right col., par. 2). Accordingly, a person having ordinary skill in the art could have experimented with various relative concentrations of the “at least two compounds” to “all acyl groups present in the at least one acyl group donor” and would have been expected to arrive at the claimed ratio range of “1.00 : 2.00 to 1.00 : 4.50” with a reasonable expectation of success. The expectation of success is reasonable because the process merely requires the production of the esters and this would have been expected to occur to some extent irrespective of the relative amounts of the two reactants.
Moreover, a person having ordinary skill in the art would have performed this optimization with knowledge of the teachings of Gumel et al. (hereinafter Gumel), which reviews the state of the art with respect to lipase-mediated transesterification of sugars with fatty acids (abstract). Specifically, Gumel teaches that “how efficiently a given lipase catalyzes a given esterification process depends on the characteristics of the substrates” (p. 2080, right col., par. 3) and in previous lipase-mediated esterification reactions of glucose with stearic acid, an excess of the fatty acid in the reaction mixture significantly increased the yield of the sugar ester with an optimal molar ratio of the fatty acid to the glucose of ~3 (i.e., ~ 1 : 3)(p. 2080, right col., par. 5). Finally, Gumel teaches that “[i]n general, the conversion rate of lipase catalyzed transesterifications involving fatty acids with 10 or fewer carbons can be improved by supplying an excess of the fatty acid” (p. 2082, left col., par. 4). As such, it would have been obvious to have optimized Siebenhaller’s relative ratios in order to arrive at a ratio wherein fatty acids are present in a higher molar ratio, especially in a range which encompasses a ratio previously known to significantly increase esterification of glucose (1 : 3). There is no evidence of record that the claimed ratio range elicits some unexpected or remarkable result, especially with the knowledge that the reaction can be “significantly increased” by providing a ratio falling within the claimed range, and especially when working with fatty acids having 10 or fewer carbons.
Thus, claim 19 is obvious over Siebenhaller, as evidenced by PubChem 1 and 2, and in view of Gumel as a result of routine experimentation.
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.
Previous provisional rejections for Double Patenting
Response to applicant’s arguments
Applicant asserts that the current claims are not obvious over the copending applications because there is no motivation to have further limited in the processes of either of the cited applications.
For at least the reasons discussed in the rejection of claim 4 under both provisional rejections, it would have been obvious to have further included a choline salt in order to improve the process (by avoiding inactivation of lipase in polar solvents) and Siebenhaller also provides sufficient teaching to routinely experiment with various amounts of choline salt. Therefore, the amended claims are similarly obvious over the copending applications in view of Siebenhaller.
Accordingly, the provisional rejections must be maintained. In order to address applicant’s amendments, new grounds of rejection are made below.
New grounds of rejection
Claims 1-3, 5-13, 16-17, and 19-20 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-8 and 16-23 of copending Application No. 17/757,528.
Although the claims at issue are not identical, they are not patentably distinct from each other for the following reasons.
Regarding claim 1, claim 1 of the copending application (hereinafter ‘528) is directed to a process for the enzymatic preparation of a sorbitol carboxylate (i.e., a sugar alcohol ester) comprising blending sorbitol (i.e., a sugar alcohol) and at least one acyl group donor and reacting the sorbitol with the at least one acyl group donor in the presence of a lipase.
Claim 1 differs because it requires a mixture composition comprising at least two selected from the group consisting of a sugar ester and a sugar alcohol from a mixture containing at least two compounds selected from the group consisting of a sugar and a sugar alcohol, while ‘528 only provides a single sugar alcohol ester (sorbitol carboxylates; see special definition in p. 3, lines 25-31 of the copending specification).
Nonetheless, the process of claim 1 of ‘528 is open to unrecited components (by virtue of the “comprising” language) and it would have therefore been obvious to have included additional sugar alcohols to, for example, prepare additional esters of additional sugar alcohols at the same time. There would have been a reasonable expectation of success because the reaction merely requires the lipase-mediated esterification of a sugar alcohol with an acyl donor and would be expected to work on any number of sugar alcohols.
And although the claims of ‘528 do not teach that the composition further comprises at least one substance selected from the group consisting of a choline salt, an ammonium salt, it would have nonetheless been obvious to have made such a modification.
For example, Siebenhaller teaches that in polar solvents, most lipases lose their esterification activity and to avoid the use of polar solvents, deep eutectic solvents can be used (p. 2, left col., par. 2). Specifically, DESs are ammonium or phosphonium salts (Id.) and Siebenhaller specifically teaches the use of choline chloride (i.e., a choline salt)(p. 3, left col., par. 3). Accordingly, because Siebenhaller teaches that polar compositions can disrupt lipase activity, it would have been obvious to have added a DES to the mixture containing polar components such as sorbitol.
Moreover, it would have been obvious to have routinely experimented with various concentrations of the DES substance to arrive at an amount of “less than 2% by weight”. There would have been a reasonable expectation of success because the experimentation would merely be expected to affect the overall efficacy of the process and because the claim already requires the other components to be at least 95%.
Regarding claim 2, claim 1 of ‘528 involves the use of sorbitol.
Regarding claim 3, 16 of ‘528 limits the acyl donor group to be a fatty acid.
Regarding claims 5-6 and 19, claim 8 of ‘528 provides a molar ratio of the sorbitol (i.e., the mixture or the primary alcohol group) of 1.00:0.50 to 1.00:5.00, which overlaps with the recited ranges of 1.00:0.08 to 1.00:10.00 (claims 5-6) and the narrower range of 1.00:2.00 to 1.00:4.50 (claim 19).
Regarding claim 7, this claim is the same as claim 5 of ‘528.
Regarding claim 8, claim 1 of ‘528 teaches a reaction temperature of 75°C to 110°C, which overlaps with the recited range of 20°C to 160°C.
Regarding claim 9, claim 6 of ‘528 teaches the pressure of less than 1 bar.
Regarding claim 10, claim 3 of ‘528 teaches that the two groups make up at least 80% by weight, based on an overall reaction mixture. This overlaps with the instantly claimed range of “at least 10% by weight”.
Regarding claim 11, claim 1 of ‘528 provides a step of “purifying the sorbitol carboxylate”. Thus, the claims of ‘711 teach removing byproducts formed in step B).
Regarding claim 12, claim 1 of ‘528 teaches a step of blending sorbitol and at least one acyl group donor. Because, for the reasons discussed above, it would have been obvious to have included other sugar alcohols, it would have similarly been obvious to have mixed the two components (e.g., by blending). And although the alcohols provided by ‘528 are liquid, this step would be the same as mixing the “form dissolved in water” when dealing with a solid form.
Regarding claim 13, claim 4 of ‘528 requires a water content less than 15% by weight. This range overlaps with “less than 17%”.
Regarding claim 16, claim 16 of ‘528 teaches that the at least one acyl group donor is selected from fatty acid esters and fatty acids.
Regarding claim 17, claim 2 of ‘528 teaches that the acyl group is from a carboxylic acid containing 2 to 34 carbon atoms or a mixture thereof. This claim reads on the instant claim.
Regarding claim 20, claim 3 of ‘528 requires that the mixture and the acyl group make up at least 80% of the overall reaction. This amount overlaps with the recited range of at least 90% by weight.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1-3, 5-13, 16-17, and 19-20 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-10, 13, and 16-18, 20-25 of copending Application No. 17/757,711.
Although the claims at issue are not identical, they are not patentably distinct from each other for the following reasons.
Regarding claim 1, claim 9 of the copending application (hereinafter ‘711) is directed to a process for the enzymatic preparation of a xylitol carboxylate (i.e., a sugar alcohol ester) comprising providing xylitol (i.e., a sugar alcohol) and at least one acyl group donor and reacting the xylitol with the at least one acyl group donor in the presence of a lipase. Claim 1 of ‘711 limits the produced xylitol carboxylate to at least one carboxylic ester of xylitol, and carboxylic esters of 1,4-anhydroxylitol, 1,4-anhydroarabitol, and 1-4,-anhydrooribitol. These are “esters…which have two different residues in terms of sugar and/or sugar alcohol residue” (xylitol, arabitol, and ribitol). As such, the process provided in ‘711 is a process for the enzymatic preparation of a mixture composition comprising at least two selected from the group consisting of a sugar ester and a sugar alcohol.
The process differs only in that the instant claim requires a mixture containing at least two compounds selected from the group consisting of a sugar and a sugar alcohol.
Nonetheless, the process of claim 9 of ‘711 is open to unrecited components (by virtue of the “comprising” language) and it would have therefore been obvious to have included additional components such as arabitol and ribitol in the starting composition in order to, for example, improve the yield of the arabitol and ribitol esters.
And although the claims of ‘711 do not teach that the composition further comprises at least one substance selected from the group consisting of a choline salt, an ammonium salt, it would have nonetheless been obvious to have made such a modification.
For example, Siebenhaller teaches that in polar solvents, most lipases lose their esterification activity and to avoid the use of polar solvents, deep eutectic solvents can be used (p. 2, left col., par. 2). Specifically, DESs are ammonium or phosphonium salts (Id.) and Siebenhaller specifically teaches the use of choline chloride (i.e., a choline salt)(p. 3, left col., par. 3). Accordingly, because Siebenhaller teaches that polar compositions can disrupt lipase activity, it would have been obvious to have added a DES to the mixture containing polar components such as xylitol.
Moreover, it would have been obvious to have routinely experimented with various concentrations of the DES substance to arrive at an amount of “less than 2% by weight”. There would have been a reasonable expectation of success because the experimentation would merely be expected to affect the overall efficacy of the process and because the claim already requires the other components to be at least 95%.
Regarding claim 2, claim 9 of ‘711 involves the use of xylitol.
Regarding claim 3, 19 of ‘711 limits the acyl donor group to be a natural fatty acid.
Regarding claims 5-6 and 19, although ‘711 doesn’t teach the recited molar ratios, it does teach the presence of these components and therefore it would have been obvious to have routinely experimented with various relative concentrations to arrive at the recited range. There is no evidence that the recited molar ratio ranges elicit some unexpected or remarkable result.
Regarding claim 7, this claim is the same as claim 12 of ‘711.
Regarding claim 8, claim 9 of ‘711 teaches a reaction temperature of 75°C to 110°C, which overlaps with the recited range of 20°C to 160°C.
Regarding claim 9, claim 13 of ‘711 teaches the pressure of less than 1 bar.
Regarding claim 10, claim 9 of ‘711 teaches that the two groups make up at least 95% by weight, based on an overall reaction mixture. This overlaps with the instantly claimed range of “at least 10% by weight”.
Regarding claim 11, claim 9 of ‘711 provides a step of “purifying the xylitol carboxylate”. Thus, the claims of ‘711 teach removing byproducts formed in step B).
Regarding claim 12, claim 9 of ‘711 teaches a step of “providing xylitol and at least one acyl group donor” and claim 10 of ‘711 teaches a step of “blending the xylitol and the at least one acyl group donor”. Because, for the reasons discussed above, it would have been obvious to have included other sugar alcohols such as arabitol and ribitol, it would have similarly been obvious to have mixed the two components. And although the alcohols provided by ‘711 are liquid, this step would be the same as mixing the “form dissolved in water” when dealing with a solid form.
Regarding claim 13, the claims of ‘711 do not teach any specific water content percentages.
Nonetheless, as shown in Siebenhaller, it was previously known that the esterification activity of lipase occurs in nearly water-free environments (p. 2, left col., par. 2). As such, it would have been obvious to have reduced the water content in the mixture containing the reactants because the amount of water would be expected to affect the lipase activity.
Additionally, it would have been obvious to have routinely experimented with various percentages of water and a person having ordinary skill in the art could have arrived at the recited range of “less than 17% by weight” with a reasonable expectation of success because the amount of water would be expected to affect lipase activity and because Siebenhaller demonstrates that nearly water-free environments (i.e., 5.4% are suitable for esterification with lipase)(p. 4, right col., par. 4).
Regarding claim 16, claim 19 of ‘711 teaches that the at least one acyl group donor is selected from fatty acid esters and fatty acids.
Regarding claim 17, claims 21 and 22 of ‘711 limit the acyl group donor to caprylic acid and oleic acid, respectively.
Regarding claim 18, claim 9 of ‘711 does not comprise the substances of instant claim 4.
Regarding claim 20, claim 9 of ‘711 requires that the mixture and the acyl group make up at least 95% of the overall reaction. This amount overlaps with the recited range of at least 90% by weight.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Conclusion
No claim is allowed.
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.
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