DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on December 02, 2025 has been entered.
Claim Status
Claims 1-14 and 19 are canceled. Thus, claims 15-18 and 20-23 as amended are examined on the merits herein.
Withdrawn Objections and Rejections
With respect to the objections and/or rejections mailed in the non-final office action on September 04, 2025:
(I) The rejection of claims 1-14 under 35 U.S.C. 103; and
(II) All rejections of claims 1-14 on the ground of nonstatutory double patenting are withdrawn in view of Applicant’s cancelation of claims 1-14 as discussed in the Claim Status section above.
(III) The rejection of claim 16 on the ground of nonstatutory double patenting as being unpatentable in view of U.S. Patent No. 11,130,905 B2 is withdrawn as ‘905 does not specifically recite the required amine-functionalized saccharide polymer required within instant claim 16.
Claim Interpretation
The Examiner notes the claim interpretations with respect to claim 1, line 5 and line 7 are withdrawn in view of the cancelation of claim 1 as discussed above.
Response to Arguments
(I) The rejection of claims 15-18 and 20-23 under 35 U.S.C. 103; and
(II) The rejection of claims 15-18 and 20-23 on the ground of nonstatutory double patenting are maintained.
Applicant argues:
(A) The applied references are not understood to disclose, teach, or suggest the features of independent claim 15, particularly at least the feature of “wherein the backbone length of the saccharide polymer is preserved when reacting the trans-vicinal diol with sodium hypochlorite pentahydrate”, see Applicant’s remarks, pg. 4, B. Independent Claim 15, paragraph 1.
(B) With respect to promoting cleavage of a vicinal diol (glycol), one having ordinary skill in the art would have no reasonable expectation of success in substituting the sodium hypochlorite of Wang with the sodium hypochlorite pentahydrate of Okada, see Applicant’s remarks, pg. 5, last paragraph of the page.
(C) There is no reasonable expectation of success for utilizing sodium hypochlorite pentahydrate to promote cleavage of a vicinal diol, see Applicant’s remarks, pg. 6, paragraph 1.
With respect to Applicant’s arguments (A)-(C), the Examiner notes these arguments are addressed with the removal of the Okada reference and the addition of the Kirihara reference as discussed in greater detail within the maintained rejections below.
Applicant further argues:
(D) Wang expressly teaches that fragmentation of dextran occurs during oxidation; Wang similarly teaches that oxidation of starch produces fragments, see Applicant’s remarks, pg. 5, paragraph 2; and consequently, Wang does not teach or suggest an oxidation process in which the backbone length of the polysaccharide is preserved, see Applicant’s arguments, pg. 5, paragraph 3.
(E) Based upon the teachings of Wang there would be no reasonable expectation of success that preservation of the backbone would be realized upon substituting the sodium hypochlorite of Wang with the sodium hypochlorite pentahydrate of Okada, see Applicant’s remarks, pg. 5, paragraph 3.
With respect to Applicant’s arguments (D)-(E), the Examiner notes Wang teaches since dextran is usually accompanied by extensive cleavage of the chain, oxidative conversion by higher concentrations of sodium hypochlorite (NaOCl) would lead to a decrease size of polyaldehyde dextran (PD) due to fragmentation, hence, less over-oxidation, see Wang, pg. 3218, bottom of left-hand column and top of right-hand column.
Accordingly, the Examiner notes fragmentation of dextran when using NaOCl is a known consideration in the art and within the scope of the artisan to address as Wang explicitly teaches higher concentrations of NaOCl lead to a decrease size of PD due to fragmentation.
Moreover, the Examiner also notes Applicant’s arguments (D)-(E) are not particularly persuasive in view of the method of claim 15 as a whole which recites a saccharide polymer comprising one or more monosaccharide units linked by glycosidic bonds, see claim 15, lines 2-4; and wherein the Examiner notes the method recited within claim 15 does not require a specific saccharide polymer nor a specific concentration range of sodium hypochlorite pentahydrate within the recited method.
Furthermore, the Examiner notes Madduri teaches an exemplary embodiment of chemically engineering the clay-controlling polymer known as amino dextran obtained by reacting dextran with sodium periodate (the oxidant), wherein said dextran comprises at least 4 monosaccharide units and wherein the backbone length of the saccharide polymer is preserved.
Accordingly, the Examiner reasonably interprets the limitation “wherein the backbone length is preserved” as argued by Applicant above is a physical limitation fulfilled by exposing any saccharide polymer comprising any backbone length to any concentration of sodium hypochlorite pentahydrate.
Thus, Applicant’s arguments (A)-(E) have been fully considered but are not found persuasive.
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.
(I) Claims 15-16 and 20-23 are rejected under 35 U.S.C. 103 as being unpatentable over Madduri et al. (Published 06 October 2016, US-20160289559-A1, PTO-892 mailed 01/28/2025) in view of Wang et al. (Published 29 July 2016, Journal of Food Science and Technology, Vol. 53, Issue 8, pp. 3215-3224, PTO-892 mailed 09/04/2025) and Kirihara et al. (Published 19 May 2019, The Journal of Organic Chemistry, Vol. 84, Issue 12, pp. 8330-8336, PTO-892).
Regarding claims 15-16 and 20-23, Madduri teaches the production of polysaccharides and polysaccharide derivatives, see paragraph [0003].
Madduri teaches functionalized polymers used to control the swelling of soils such as, for example soils containing clays; wherein these clay-controlling polymers are preferably chemically engineered (functionalized and optionally modified, for example by oxidation), see paragraph [0030].
Madduri teaches an exemplary embodiment of chemically engineering the clay-controlling polymer known as amino dextran obtained by reacting dextran with sodium periodate (the oxidant) in water at room temperature (preferable from about 20-22°C.), followed by ethylene diamine addition in water at room temperature, and followed by reduction of the formed imine with sodium borohydride in water at room temperature, see pg. 5, right column, example 3, paragraph [0047]. Madduri depicts the structure of amino dextran as,
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, see Sheet 1 of 3, Figure 1A.
The Examiner respectfully notes that the amino dextran of Madduri as depicted above is an amine-functionalized saccharide polymer, exemplified as a secondary amino dextran (the amine functionalized dextran, required in claim 15, lines 15-16 and claim 16). Accordingly, the Examiner notes the exemplified amino dextran of Madduri above corresponds to the amine-functionalized saccharide polymer having the secondary amine directly covalently bound to a carbon atom of a monosaccharide unit that has undergone oxidative opening, required in claim 15, last five lines of the claim.
The Examiner notes the exemplified amino dextran of Madduri above has its backbone length preserved when reacting the trans-vicinal diol, as required within claim 15, lines 9-10.
The Examiner notes the amino dextran as discussed above depicts a primary alcohol and a secondary amine at the site of oxidative opening, wherein the primary alcohol being formed from a carbon atom of a monosaccharide unit that has undergone oxidative opening, as required in claim 20.
The Examiner further notes the exemplified amino dextran of Madduri above depicts the polymer further comprises one or more sites of oxidative opening that are not amine-functionalized as required by claim 23.
Madduri teaches preferably the polysaccharide is dextran containing multiple alkyl, amine and/or alkyl/amine moieties wherein, for example the amine moieties are selected from the group consisting of amine, diamine, tetra-amine moieties, and combinations thereof (e.g. bears two secondary or two tertiary amines at the site of oxidative opening, required in claim 22), see paragraph [0011].
Although, Madduri does not teach the sodium hypochlorite pentahydrate as the oxidative agent, required in claim 15, line 2 and claim 21.
However, in the same field of endeavor of oxidizing dextran, Wang teaches sodium hypochlorite (NaOCl) has been applied to oxidatively modify starch to produce amylose aldehydes as demonstrated in the following reaction,
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see pg. 3216, left column, second full paragraph. The Examiner respectfully notes when the saccharide polymer reacts with the sodium hypochlorite (NaOCl) as taught by the reaction scheme of Wang above; the trans-vicinal diol of the monosaccharide unit of said saccharide polymer oxidatively opens to form a dialdehyde.
Wang teaches it is possible by taking a similar approach utilizing NaOCl as the oxidizing agent, polyaldehyde dextran (PD) can be formed, see pg. 3216, left column, paragraphs 1-2.
Although, Wang does not teach the pentahydrate form of sodium hypochlorite as required in the instant claims above, however, Kirihara teaches sodium hypochlorite pentahydrate as a reagent for the cleavage of trans-cyclic glycols, see pg. 8330, title; wherein sodium hypochlorite pentahydrate can be used toward the efficient glycol cleavage of trans-cyclic glycols which are generally resistant to this transformation, see pg. 8330, abstract.
Kirihara also teaches the reaction of cis-cyclic glycols with sodium hypochlorite pentahydrate is slower than that observed for the corresponding trans-isomer, and wherein this trans-selectivity is in sharp contrast to traditional oxidants used for glycol cleavage, see pg. 8330, abstract.
With respect to the limitation “wherein the amine-functionalized saccharide polymer bears a carboxylic acid and the secondary amine at the site of oxidative opening, the carboxylic acid being formed from a carbon atom of the monosaccharide unit that has undergone oxidative opening”, required in claim 21, lines 2-5; the Examiner reasonably interprets this limitation to be a physical consequence of oxidatively opening the trans-vicinal diol of the saccharide polymer using the sodium hypochlorite pentahydrate as evidenced by Kirihara which discloses the formation of a carboxylic acid at the site of oxidative opening after oxidation of a trans-cyclic glycol as exemplified in compound 3d in Table 2 of Kirihara, see pg. 8331, Table 2, compound 3d; and as further evidenced by the specification which discloses hypochlorite oxidation may produce a limited amount of carboxylic acids when oxidatively opening a trans-vicinal diol (pg. 6, paragraph [0014], lines 4-5 and pg. 10, scheme 1).
It would have been prima facie obvious to one of ordinary skill in the art at the invention’s effective filing date to have substituted the sodium periodate as the oxidating agent as taught by Madduri above for the sodium hypochlorite pentahydrate as the oxidating reagent as taught by the combination of Wang and Kirihara above as within the scope of the artisan as combining prior art elements according to known methods to yield predictable results.
As the Examiner notes Madduri exemplifies the polysaccharide comprising the trans-vicinal diol as dextran, wherein said dextran is chemically modified via oxidation using the exemplified sodium periodate as taught by Madduri above.
Additionally, the Examiner also particularly notes Wang explicitly suggests a possible approach utilizing sodium hypochlorite (NaOCl) as the oxidizing agent to form polyaldehyde dextran (PD); and wherein the Examiner further particularly notes one of ordinary skill would have been particularly motivated to have specifically used sodium hypochlorite pentahydrate as the oxidizing agent; as Kirihara explicitly teaches sodium hypochlorite pentahydrate as a reagent for efficient glycol cleavage of trans-cyclic glycols which are generally resistant to this transformation and wherein this trans-selectivity is in sharp contrast to traditional oxidants used for glycol cleavage as discussed above.
One of ordinary skill in the art would have been motivated to have made the substitutions above in order to produce the oxidized and amine-derivatized polysaccharide derivatives exemplified and taught by Madduri above. One of ordinary skill in the art would have had a reasonable expectation of success to have made said substitutions as discussed above because Wang teaches the use of sodium hypochlorite in oxidizing trans-vicinal diols of polysaccharides, and explicitly suggests the possible use of sodium hypochlorite in forming polyaldehyde dextran; and wherein Kirihara specifically teaches the use of sodium hypochlorite pentahydrate as a reagent for the efficient cleavage of trans-cyclic glycols as discussed above.
Consequently, it would have been prima facie obvious to one of ordinary skill in the art before the invention was filed to have substituted the sodium periodate as the oxidating agent as taught by Madduri above for the sodium hypochlorite pentahydrate as the oxidating reagent as taught by the combination of Wang and Kirihara above as a simple substitution of one known element for another within the scope of the artisan by combining prior art elements according to known methods to yield predictable results. One of ordinary skill in the art would have been motivated to have substituted the sodium periodate of Madduri for the sodium hypochlorite pentahydrate as taught by Wang and Kirihara above in order to produce the oxidized dextran for further derivatization within amine groups as exemplified and taught by Madduri above. One of ordinary skill in the art would have had a reasonable expectation of success to have substituted the sodium periodate of Madduri for the sodium hypochlorite pentahydrate of Wang and Kirihara; because Wang explicitly suggests the possibility of utilizing NaOCl as the oxidizing agent in which polyaldehyde dextran can be formed; and wherein Kirihara specifically teaches the use of sodium hypochlorite pentahydrate as a reagent for the efficient cleavage of trans-cyclic glycols as discussed above.
Thus, the claimed invention as a whole would have been prima facie obvious over the combined teachings of the prior art.
(II) Claims 17-18 are rejected under 35 U.S.C. 103 as being unpatentable over Madduri et al. (Published 06 October 2016, US-20160289559-A1, PTO-892 mailed 01/28/2025), Wang et al. (Published 29 July 2016, Journal of Food Science and Technology, Vol. 53, Issue 8, pp. 3215-3224, PTO-892 mailed 09/04/2025) and Kirihara et al. (Published 19 May 2019, The Journal of Organic Chemistry, Vol. 84, Issue 12, pp. 8330-8336, PTO-892) as applied to claims 15-16 and 20-23 above, and further in view of Anderson et al. (Published 15 May 2013, WO-2013068771-A1, PTO-892 mailed 01/28/2025).
Madduri, Wang and Kirihara address claims 15-16 and 20-23 as written above. Madduri further teaches methods for the stabilization of clays, shales and other clay-containing materials and soils with polymers containing dextran, dextran derivatives, and other substituted polysaccharides, see paragraph [0003].
Although, Madduri does not teach the amine-functionalized saccharide polymer comprises maltodextrin, required in claims 17-18.
However, in the same field of endeavor of saccharide compositions, Anderson teaches a water-based wellbore fluid comprising water and a hydration inhibitor including a hydroxyalkyl polysaccharide with a weight average molecular mass of less than 5,000, see pg. 4, lines 1-5.
Anderson teaches the polysaccharide is typically an oligosaccharide, see pg. 4, lines 12-13; and when the polysaccharide is an oligosaccharide it may be formed from between 2 and 10 monosaccharide monomers, see pg. 4, lines 17-18.
Anderson teaches the polysaccharide may be a depolymerized derivative of one or more of the polymers including maltodextrin and dextran and alkyl derivatives thereof, see pg. 4, lines 26-31.
It would have been prima facie obvious to one of ordinary skill in the art before the invention was filed to have included maltodextrin and/or an alkyl derivative of maltodextrin as taught by Anderson above into the saccharide polymer as taught by Madduri above as within the scope of the artisan as combining prior art elements according to known methods to yield predictable results. One of ordinary skill would have been motivated to use polymers containing dextran, dextran derivatives, and other substituted polysaccharides as methods for the stabilization of clays and shales as taught by Madduri above. One of ordinary skill in the art would have had a reasonable expectation of success to have included maltodextrin and/or an alkyl derivative of maltodextrin as taught by Anderson into the saccharide polymer as taught by Madduri, because Anderson teaches the polysaccharide may be a depolymerized derivative of one or more of maltodextrin and dextran; and Madduri teaches the polysaccharide contains dextran derivatives and other substituted polysaccharides as discussed above.
Thus, the claimed invention as a whole would have been prima facie obvious over the combined teachings of the prior art.
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.
(I) Claims 15-16 and 20-23 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 13 and 20-21 of U.S. Patent No. 11,028,314 B2 (Applicant: Integrity Bio-Chemicals, LLC, PTO-892 mailed 01/28/2025) in view of Wang et al. (Published 29 July 2016, Journal of Food Science and Technology, Vol. 53, Issue 8, pp. 3215-3224, PTO-892 mailed 09/04/2025) and Kirihara et al. (Published 19 May 2019, The Journal of Organic Chemistry, Vol. 84, Issue 12, pp. 8330-8336, PTO-892). Although the claims at issue are not identical, they are not patentably distinct from each other because both sets of claims are directed to methods of providing amine-functionalized saccharide polymers.
Reference claim 13 recites a method comprising providing a clay stabilizing composition comprising: an amine-functionalized dextrin compound, the amine-functionalized dextrin compound comprising 2 to about 20 glucose units; a portion of the glucose units being oxidatively opened and functionalized with at least one amine group at a site of oxidative opening, and an amine-functionalized dextran polymer, the amine-functionalized dextran polymer comprising a plurality of glucose; and a portion of the glucose units being oxidatively opened and functionalized with at least one amine group at a site of oxidative opening; and introducing the clay stabilizing composition into a subterranean formation bearing a clay-containing mineral; and interacting the amine-functionalized dextrin compound and the amine-functionalized dextran polymer with the clay-containing mineral to affect stabilization thereof.
Reference claim 20 recites the amine-functionalized dextran polymer bears a secondary amine or a tertiary amine that is directly covalently bound to each site of oxidative opening.
Reference claim 21 recites wherein the amine-functionalized dextran polymer bears a primary alcohol and the secondary amine or the tertiary amine at each site of oxidative opening.
Although, ‘314 does not recite the sodium hypochlorite pentahydrate as the oxidative agent, required in instant claim 15, line 2 and instant claim 21.
However, in the same field of endeavor of oxidizing polysaccharides, Wang teaches sodium hypochlorite (NaOCl) has been applied to oxidatively modify starch to produce amylose aldehydes as demonstrated in the following reaction,
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see pg. 3216, left column, second full paragraph. The Examiner respectfully notes when the saccharide polymer reacts with the sodium hypochlorite (NaOCl) as taught by the reaction scheme of Wang above; the trans-vicinal diol of the monosaccharide unit of said saccharide polymer oxidatively opens to form a dialdehyde.
Wang teaches it is possible by taking a similar approach utilizing NaOCl as the oxidizing agent polyaldehyde dextran (PD) can be formed, see pg. 3216, left column, paragraphs 1-2.
Although, Wang does not teach the pentahydrate form of sodium hypochlorite as required in the instant claims above, however, Kirihara teaches sodium hypochlorite pentahydrate as a reagent for the cleavage of trans-cyclic glycols, see pg. 8330, title; wherein sodium hypochlorite pentahydrate can be used toward the efficient glycol cleavage of trans-cyclic glycols which are generally resistant to this transformation, see pg. 8330, abstract.
Kirihara teaches the reaction of cis-cyclic glycols with sodium hypochlorite pentahydrate is slower than that observed for the corresponding trans-isomer, and wherein this trans-selectivity is in sharp contrast to traditional oxidants used for glycol cleavage, see pg. 8330, abstract.
It would have been prima facie obvious to one of ordinary skill in the art before the invention was filed to have used the sodium hypochlorite pentahydrate as the oxidating reagent as taught by the combination of Wang and Kirihara above in order to provide the composition of ‘314 containing an amine-functionalized dextran polymer wherein a portion of the glucose are being oxidatively opened and functionalized with at least one amine group as recited within reference claim 13 of ‘314 as discussed above as within the scope of the artisan as combining prior art elements according to known methods to yield predictable results. One of ordinary skill in the art would have been motivated and would have had a reasonable expectation of success to have used the sodium hypochlorite pentahydrate as the oxidant to oxidatively open the dextran polymer of ‘314 above, as Wang explicitly suggests the possible use of sodium hypochlorite in forming polyaldehyde dextran and Kirihara explicitly teaches sodium hypochlorite pentahydrate as a reagent for efficient glycol cleavage of trans-cyclic glycols as discussed above.
Thus, the claimed invention as a whole would have been prima facie obvious over the combined recitations of ‘314 and the teachings of the prior art.
(II) Claims 17-18 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 13, 16 and 20-21 of U.S. Patent No. 11,028,314 B2 (Applicant: Integrity Bio-Chemicals, LLC, PTO-892 mailed 01/28/2025) in view of Wang et al. (Published 29 July 2016, Journal of Food Science and Technology, Vol. 53, Issue 8, pp. 3215-3224, PTO-892 mailed 09/04/2025), Kirihara et al. (Published 19 May 2019, The Journal of Organic Chemistry, Vol. 84, Issue 12, pp. 8330-8336, PTO-892) and Anderson et al. (Published 15 May 2013, WO-2013068771-A1, PTO-892 mailed 01/28/2025). Although the claims at issue are not identical, they are not patentably distinct from each other because both sets of claims are directed to methods of providing amine-functionalized saccharide polymers.
‘314 recites and Wang and Kirihara teach as discussed above. ‘314 further recites in reference claim 16 wherein the amine-functionalized dextrin compound is an amine-functionalized maltodextrin compound.
Although, ‘314 does not recite wherein the amine functionalized saccharide polymer has 3 to about 20 monosaccharide units, required instant claim 17.
However, in the in the same field of endeavor of saccharide compositions, Anderson teaches a water-based wellbore fluid comprising water and a hydration inhibitor including a hydroxyalkyl polysaccharide with a weight average molecular mass of less than 5,000, see pg. 4, lines 1-5.
Anderson teaches the polysaccharide is typically an oligosaccharide, see pg. 4, lines 12-13; and when the polysaccharide is an oligosaccharide it may be formed from between 2 and 10 monosaccharide monomers, see pg. 4, lines 17-18.
Anderson teaches the polysaccharide may be a depolymerized derivative of one or more of the polymers including maltodextrin and dextran and alkyl derivatives thereof, see pg. 4, lines 26-31.
Anderson teaches the use of the water-based well-bore fluid in drilling a subterranean hole, see pg. 15, lines 15-20.
It would have been prima facie obvious to one of ordinary skill in the art before the invention was filed to have incorporated the teachings of Anderson above into the method of providing the clay-stabilizing composition as recited by ‘314 above as within the scope of the artisan as combining prior art elements according to known methods to yield predictable results. One of ordinary skill in the art would have been motivated to incorporate the teachings of Anderson as discussed above into the method of providing the clay stabilizing composition as recited by ‘314 above; as ‘314 recites introducing said composition into a subterranean formation within reference claim 13 of ‘314. One of ordinary skill in the art would have had a reasonable expectation of success to have incorporated the teachings of Anderson into the method recited by ‘314 above; as both ‘314 and Anderson are drawn to using maltodextrin and dextran comprising polysaccharide derivatives within compositions and introducing said compositions into subterranean formations as discussed above.
Thus, the claimed invention as a whole would have been prima facie obvious over the combined recitations of ‘314 and the teachings of the prior art.
(III) Claims 15, 17-18 and 20-23 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 11 and 18-19 of U.S. Patent No. 11,130,905 B2 (Applicant: Integrity Bio-Chemicals, LLC, PTO-892 mailed 01/28/2025) in view of Wang et al. (Published 29 July 2016, Journal of Food Science and Technology, Vol. 53, Issue 8, pp. 3215-3224, PTO-892 mailed 09/04/2025) and Kirihara et al. (Published 19 May 2019, The Journal of Organic Chemistry, Vol. 84, Issue 12, pp. 8330-8336, PTO-892). Although the claims at issue are not identical, they are not patentably distinct from each other because both sets of claims are directed to methods of providing amine-functionalized saccharide polymers.
Reference claim 11 recites a method comprising providing a clay stabilizing composition comprising: an amine-functionalized dextrin compound, the amine-functionalized dextrin compound comprising 2 to about 20 glucose units; a portion of the glucose units being oxidatively opened and functionalized with at least one amine group at a site of oxidative opening; introducing the clay stabilizing composition into a subterranean formation bearing a clay-containing mineral; and interacting the amine-functionalized dextrin compound with the clay-containing mineral to affect stabilization thereof.
Reference 18 recites wherein the amine-functionalized dextrin compound bears a secondary amine or a tertiary amine that is directly covalently bound to each site of oxidative opening.
Reference claim 19 recites wherein the amine-functionalized dextrin compound bears a primary alcohol and the secondary amine or the tertiary amine at each site of oxidative opening.
Although, ‘905 does not recite the sodium hypochlorite pentahydrate as the oxidative agent, required in instant claim 15, line 2 and instant claim 21.
However, in the same field of endeavor of oxidizing polysaccharides, Wang and Kirihara teach as set forth above.
It would have been prima facie obvious to one of ordinary skill in the art before the invention was filed to have used the sodium hypochlorite pentahydrate as the oxidating reagent as taught by the combination of Wang and Kirihara above in order to provide the composition of ‘905 containing an amine-functionalized dextrin polymer wherein a portion of the glucose are being oxidatively opened and functionalized with at least one amine group as recited within reference claim 11 of ‘905 as discussed above as within the scope of the artisan as combining prior art elements according to known methods to yield predictable results. One of ordinary skill in the art would have been motivated and would have had a reasonable expectation of success to have used the sodium hypochlorite pentahydrate as the oxidant to oxidatively open the dextrin polymers of ‘905 above, as Wang explicitly teaches the use of sodium hypochlorite in chemically modifying a polysaccharide comprising a trans-vicinal diol, exemplifying starch, to form a dialdehyde of the oxidatively opened starch; and Kirihara explicitly teaches sodium hypochlorite pentahydrate as a reagent for efficient glycol cleavage of trans-cyclic glycols as discussed above.
Thus, the claimed invention as a whole would have been prima facie obvious over the combined recitations of ‘905 and the teachings of the prior art.
(IV) Claims 15-16 and 20-23 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-5 and 9-10 of U.S. Patent No. 11,725,134 B2 (Applicant: Integrity Bio-Chemicals, LLC, PTO-892 mailed 01/28/2025) in view of Kirihara et al. (Published 19 May 2019, The Journal of Organic Chemistry, Vol. 84, Issue 12, pp. 8330-8336, PTO-892). Although the claims at issue are not identical, they are not patentably distinct from each other because both sets of claims are directed to methods of providing amine-functionalized saccharide polymers.
Reference claim 1 recites a method providing a fracturing fluid comprising an aqueous fluid, a mild oxidant, and a partially oxidized amine-functionalized polysaccharide in which glycosidic bonds are retained from a parent polysaccharide and partial oxidation comprises oxidative opening of a monosaccharide unit of the parent polysaccharide;
wherein an amine moiety is located at a site of oxidative opening; and
introducing the fracturing liquid into a subterranean formation comprising shale.
Reference claim 2 recites the parent polysaccharide comprises dextran, levan, or a guar.
Reference claim 3 recites the parent polysaccharide comprises dextran or dextrin.
Reference claim 4 recites wherein the dextrin comprises maltodextrin.
Reference claim 5 recites wherein the parent polysaccharide comprises a plurality of monosaccharide units and about 5-80% of the plurality of monosaccharide units are oxidatively opened and near an amine moiety.
Reference claim 9 recites wherein the amine comprises an alkylamine.
Reference claim 10 recites wherein the mild oxidant is selected from the group consisting of and include sodium hypochlorite.
Although, ‘134 does not recite (a) the sodium hypochlorite pentahydrate as the oxidative agent, required in instant claim 15, line 2 and instant claim 21; and (b) wherein the amine-functionalized saccharide polymer bears two secondary or tertiary amines at one or more sites of oxidative opening, required in instant claim 22.
However, in the same field of endeavor of oxidizing polysaccharides, with respect to limitation (a), Kirihara teaches as set forth above.
With respect to limitation (b), ‘134 recites within reference claim 1 a partially oxidized amine-functionalized polysaccharide wherein partial oxidation comprises oxidative opening of a monosaccharide unit of the parent polysaccharide wherein an amine moiety is located at a site of oxidative opening. Additionally, as evidenced by the specification the Examiner reasonably interprets the oxidative opening of the amine-functionalized polysaccharide as recited within reference claim 1 includes two secondary or tertiary amines; as evidenced by the specification of ‘134 which recites “According to various embodiments of the present disclosure, each site of oxidative opening in a partially oxidized polysaccharide may comprise from zero to two amine groups” (see Col. 10, lines 30-35).
It would have been prima facie obvious to one of ordinary skill in the art before the invention was filed to have used the sodium hypochlorite pentahydrate as the oxidating reagent as taught by Kirihara above in the method recited by ‘134 above as within the scope of the artisan as combining prior art elements according to known methods to yield predictable results. One of ordinary skill in the art would have been motivated to use the sodium hypochlorite pentahydrate as the oxidant in order to provide the fracturing fluid of ‘134 containing an amine-functionalized polysaccharide wherein a portion of the glucose are being oxidatively opened and functionalized as recited within reference claim 1 of ‘134 as discussed above.
One of ordinary skill in the art would have had a reasonable expectation of success to have used the sodium hypochlorite pentahydrate as the oxidant to oxidatively open the polysaccharide polymers of ‘134 above, as Kirihara explicitly teaches sodium hypochlorite pentahydrate as a reagent for efficient glycol cleavage of trans-cyclic glycols as discussed above.
Thus, the claimed invention as a whole would have been prima facie obvious over the combined recitations of ‘134 and the teachings of the prior art.
(V) Claims 17-18 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-5 and 9-10 of U.S. Patent No. 11,725,134 B2 (Applicant: Integrity Bio-Chemicals, LLC, PTO-892 mailed 01/28/2025) in view of Kirihara et al. (Published 19 May 2019, The Journal of Organic Chemistry, Vol. 84, Issue 12, pp. 8330-8336, PTO-892) and Anderson et al. (Published 15 May 2013, WO-2013068771-A1, PTO-892 mailed 01/28/2025). Although the claims at issue are not identical, they are not patentably distinct from each other because both sets of claims are directed to methods of providing amine-functionalized saccharide polymers.
‘134 recites and Kirihara teaches as discussed above. Although, ‘134 does not recite wherein the amine functionalized saccharide polymer has 3 to about 20 monosaccharide units, required instant claim 17.
However, in the in the same field of endeavor of saccharide compositions, Anderson teaches as set forth above.
It would have been prima facie obvious to one of ordinary skill in the art before the invention was filed to have incorporated the teachings of Anderson above into the method of providing the fracturing fluid as recited by ‘134 above as within the scope of the artisan as combining prior art elements according to known methods to yield predictable results. One of ordinary skill in the art would have been motivated to incorporate the teachings of Anderson as discussed above into the method of providing the fracturing fluid as recited by ‘134 above; as ‘134 recites introducing said fracturing fluid into a subterranean formation as recited within reference claim 1 of ‘134. One of ordinary skill in the art would have had a reasonable expectation of success to have incorporated the teachings of Anderson into the method recited by ‘134 above; as both ‘134 and Anderson are drawn to using maltodextrin comprising polysaccharide derivatives within fluids and introducing said fluids into subterranean formations as discussed above.
Thus, the claimed invention as a whole would have been prima facie obvious over the combined recitations of ‘134 and the teachings of the prior art.
(VI) Claims 15-16 and 20-23 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-4 and 9 of U.S. Patent No. 11,827,846 B2 (Applicant: Integrity Bio-Chemicals, LLC, PTO-892 mailed 01/28/2025) in view of Wang et al. (Published 29 July 2016, Journal of Food Science and Technology, Vol. 53, Issue 8, pp. 3215-3224, PTO-892 mailed 09/04/2025) and Kirihara et al. (Published 19 May 2019, The Journal of Organic Chemistry, Vol. 84, Issue 12, pp. 8330-8336, PTO-892). Although the claims at issue are not identical, they are not patentably distinct from each other because both sets of claims are directed to methods of providing amine-functionalized saccharide polymers.
Reference claim 1 recites a method providing a fracturing fluid comprising an aqueous fluid, and a partially oxidized amine-functionalized polysaccharide in which glycosidic bonds are retained from a parent polysaccharide and partial oxidation comprises oxidative opening of a monosaccharide unit of the parent polysaccharide;
wherein an amine moiety is located at a site of oxidative opening; and
introducing the fracturing liquid into a subterranean formation comprising a clay containing-formation.
Reference claim 2 recites the parent polysaccharide comprises dextran, levan, or a guar.
Reference claim 3 recites the parent polysaccharide comprises dextran or dextrin.
Reference claim 4 recites 5%-80% of the plurality of monosaccharide units are oxidatively opened and bear an amine moiety at the site of oxidative opening.
Reference claim 9 recites wherein the amine comprises an alkylamine.
Although, ‘846 does not recite (a) the sodium hypochlorite pentahydrate as the oxidative agent, required in instant claim 15, line 2 and claim 21; and (b) “wherein the amine-functionalized saccharide polymer bears two secondary or tertiary amines at one or more sites of oxidative opening”, required in instant claim 22.
However, in the same field of endeavor of oxidizing polysaccharides, with respect to limitation (a), Wang and Kirihara teach as set forth above.
With respect to limitation (b), ‘846 recites in reference claim 1 a partially oxidized amine-functionalized polysaccharide wherein partial oxidation comprises oxidative opening of a monosaccharide unit of the parent polysaccharide wherein an amine moiety is located at a site of oxidative opening. Additionally, as evidenced by the specification the Examiner reasonably interprets the oxidative opening of the amine-functionalized polysaccharide as recited in reference claim 1 includes two secondary or tertiary amines; as evidenced by the specification of ‘846 which recites “According to various embodiments of the present disclosure, each site of oxidative opening in a partially oxidized polysaccharide may comprise from zero to two amine groups” (see Col. 9, lines 3-6).
It would have been prima facie obvious to one of ordinary skill in the art before the invention was filed to have used the sodium hypochlorite pentahydrate as the oxidating reagent as taught by the combination of Wang and Kirihara above in order to provide the fracturing fluid of ‘846 containing an amine-functionalized polysaccharide wherein a portion of the glucose are being oxidatively opened and functionalized as recited within reference claim 1 of ‘846 as discussed above as within the scope of the artisan as combining prior art elements according to known methods to yield predictable results. One of ordinary skill in the art would have been motivated and would have had a reasonable expectation of success to use the sodium hypochlorite pentahydrate as the oxidant to oxidatively open the polysaccharide polymers of ‘846 above, as Wang explicitly teaches the use of sodium hypochlorite in chemically modifying a polysaccharide comprising a trans-vicinal diol, exemplifying starch, to form a dialdehyde of the oxidatively opened starch; and Kirihara explicitly teaches sodium hypochlorite pentahydrate as a reagent for efficient glycol cleavage of trans-cyclic glycols as discussed above.
Thus, the claimed invention as a whole would have been prima facie obvious over the combined recitations of ‘846 and the teachings of the prior art.
(VII) Claims 17-18 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-4 and 9 of U.S. Patent No. 11,827,846 B2 (Applicant: Integrity Bio-Chemicals, LLC, PTO-892 mailed 01/28/2025) in view of Wang et al. (Published 29 July 2016, Journal of Food Science and Technology, Vol. 53, Issue 8, pp. 3215-3224, PTO-892 mailed 09/04/2025), Kirihara et al. (Published 19 May 2019, The Journal of Organic Chemistry, Vol. 84, Issue 12, pp. 8330-8336, PTO-892) and Anderson et al. (Published 15 May 2013, WO-2013068771-A1, PTO-892 mailed 01/28/2025). Although the claims at issue are not identical, they are not patentably distinct from each other because both sets of claims are directed to methods of providing amine-functionalized saccharide polymers.
‘846 recites and Wang and Kirihara teach as discussed above. Although, ‘846 does not recite wherein the amine functionalized saccharide polymer has 3 to about 20 monosaccharide units, required instant claim 17.
However, in the in the same field of endeavor of saccharide compositions, Anderson teaches as set forth above.
It would have been prima facie obvious to one of ordinary skill in the art before the invention was filed to have incorporated the teachings of Anderson above into the method of providing the fracturing fluid as recited by ‘846 above as within the scope of the artisan as combining prior art elements according to known methods to yield predictable results. One of ordinary skill in the art would have been motivated to incorporate the teachings of Anderson as discussed above into the method of providing the fracturing fluid as recited by ‘846 above; as ‘846 recites introducing said fracturing fluid into a subterranean formation as recited within reference claim 1 of ‘846. One of ordinary skill in the art would have had a reasonable expectation of success to have incorporated the teachings of Anderson into the method recited by ‘846 above; as both ‘846 and Anderson are drawn to using dextrin comprising polysaccharide derivatives within fluids and introducing said fluids into subterranean formations as discussed above.
Thus, the claimed invention as a whole would have been prima facie obvious over the combined recitations of ‘846 and the teachings of the prior art.
(VIII) Claims 15-17 and 20-23 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 8 and 10-13 of U.S. Patent No. 11,767,375 B2 (Applicant: Integrity Bio-Chemicals, LLC, PTO-892 mailed 01/28/2025) in view of Wang et al. (Published 29 July 2016, Journal of Food Science and Technology, Vol. 53, Issue 8, pp. 3215-3224, PTO-892 mailed 09/04/2025) and Kirihara et al. (Published 19 May 2019, The Journal of Organic Chemistry, Vol. 84, Issue 12, pp. 8330-8336, PTO-892). Although the claims at issue are not identical, they are not patentably distinct from each other because both sets of claims are directed to methods of providing amine-functionalized saccharide polymers.
Reference claim 8 recites a method exposing a saccharide polymer with an oxidizing agent to form a site of oxidative opening bearing at least one aldehyde upon the saccharide polymer, the site of oxidative opening comprising an oxidatively opened monosaccharide unit;
exposing the at least one aldehyde to an aminocarboxylic acid to form an imine intermediate at the site of oxidative opening, and reducing the imine intermediate to form a saccharide polymer having the at least one aminocarboxylic acid bound through the nitrogen at the site of oxidative opening.
Reference claim 10, recites the saccharide polymer comprises at least one polysaccharide selected from the group consisting of dextran, a levan, a pectin, a guar and any combination thereof.
Reference claim 11 recites the saccharide polymer comprises an oligosaccharide having 3 to about 20 monosaccharide units.
Reference claim 12 recites wherein two aminocarboxylic acids are covalently bound through nitrogen at the site of oxidative opening, or one aminocarboxylic acid is covalently bound through nitrogen at the site of oxidative opening in combination with a primary alcohol or a carboxylic acid derived from a carbon atom of an oxidatively opened monosaccharide unit.
Reference claim 13, recites the oxidizing agent comprises sodium periodate.
Although, ‘375 does not recite the sodium hypochlorite pentahydrate as the oxidative agent, required in instant claim 15, line 2 and instant claim 21.
However, in the same field of endeavor of oxidizing polysaccharides, Wang and Kirihara teach as set forth above.
It would have been prima facie obvious to one of ordinary skill in the art before the invention was filed to have substituted the sodium periodate as recited by ‘375 above for the sodium hypochlorite pentahydrate as the oxidating reagent as taught by the combination of Wang and Kirihara above in the method of exposing a saccharide polymer to an oxidizing agent as recited in reference claim 8 of ‘375 above as combining prior art elements according to known methods to yield predictable results. One of ordinary skill in the art would have been motivated and would have had a reasonable expectation of success to use the sodium hypochlorite pentahydrate as the oxidant to oxidatively open the polysaccharide polymers of ‘375 above, as Wang explicitly teaches the use of sodium hypochlorite in chemically modifying a polysaccharide comprising a trans-vicinal diol, exemplifying starch, to form a dialdehyde of the oxidatively opened starch; and Kirihara explicitly teaches sodium hypochlorite pentahydrate as a reagent for efficient glycol cleavage of trans-cyclic glycols.
Thus, the claimed invention as a whole would have been prima facie obvious over the combined recitations of ‘375 and the teachings of the prior art.
(IX) Claim 18 is rejected on the ground of nonstatutory double patenting as being unpatentable over claims 8 and 10-13 of U.S. Patent No. 11,767,375 B2 (Applicant: Integrity Bio-Chemicals, LLC, PTO-892 mailed 01/28/2025) in view of Wang et al. (Published 29 July 2016, Journal of Food Science and Technology, Vol. 53, Issue 8, pp. 3215-3224, PTO-892 mailed 09/04/2025), Kirihara et al. (Published 19 May 2019, The Journal of Organic Chemistry, Vol. 84, Issue 12, pp. 8330-8336, PTO-892) and Anderson et al. (Published 15 May 2013, WO-2013068771-A1, PTO-892 mailed 01/28/2025). Although the claims at issue are not identical, they are not patentably distinct from each other because both sets of claims are directed to methods of providing amine-functionalized saccharide polymers.
‘375 recites and Wang and Kirihara teach as discussed above. Although, ‘375 does not recite wherein the amine functionalized saccharide polymer further comprises maltodextrin.
However, in the in the same field of endeavor of saccharide compositions, Anderson teaches as set forth above.
It would have been prima facie obvious to one of ordinary skill in the art before the invention was filed to have incorporated the teachings of Anderson above into the method of reference claim 8 as recited by ‘375 above as within the scope of the artisan as combining prior art elements according to known methods to yield predictable results. One of ordinary skill in the art would have been motivated to incorporate the teachings of Anderson as discussed above into the method of reference claim 8 as recited by ‘375 above; as ‘375 recites a saccharide polymer, wherein said saccharide polymer comprises at least one polysaccharide selected from and including dextran. One of ordinary skill in the art would have had a reasonable expectation of success to have incorporated the teachings of Anderson into the method of reference claim 8 recited by ‘375 above; as both ‘375 and Anderson are drawn to polysaccharide derivatives comprising dextran.
Thus, the claimed invention as a whole would have been prima facie obvious over the combined recitations of ‘375 and the teachings of the prior art.
Conclusion
No claims are allowed in this action.
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/JARET J CREWS/Examiner, Art Unit 1691
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691
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