DETAILED OFFICIAL 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 .
Examiner Note
It is noted that all references hereinafter to Applicant’s specification (“spec”) are to the published application US 2023/0220217, unless stated otherwise. Further, any italicized text utilized hereinafter is to be interpreted as emphasis placed thereupon.
Response to Amendment
The Amendment filed 26 February 2026 in response to the Non-Final rejection dated 26 November 2025 (hereinafter “NFOA”) has been entered. Claims 1-11 and 15 have been canceled; claims 12-13 have been amended; new claims 16-23 have been added. As such, claims 12-14 and 16-23 remain pending, claims 13-14 remain withdrawn, and claims 12 and 16-23 are under consideration on the merits.
The cancelation of claim 8 has overcome the rejection of claim 8 under 35 U.S.C. 112(b) [NFOA, ¶6-10] – the 112(b) rejection has been withdrawn. The cancelation of claim 6 has overcome the rejection of claim 6 under 35 U.S.C. 112(d) [NFOA, ¶11-15] – the 112(d) rejection has been withdrawn.
The cancelation of the claims have overcome the rejections under 35 U.S.C. 102(a)(1) [NFOA, ¶18-36] and 35 U.S.C. 103 [NFOA, ¶39-44]. As such, the 102(a)(1) rejection and 103 rejection have been withdrawn.
New grounds of rejection are set forth herein, necessitated by the amendments to the claims.
Election by Original Presentation
Newly submitted claim 21 is directed to an invention that is independent or distinct from the invention originally claimed for the following reasons: claim 21 includes the previously elected species of the modified natural product having “a melting point of 40 °C or more” as well as the previously non-elected species “does not have a melting point”.
Since applicant has received an action on the merits for the originally presented invention (Species I-A, claim 8, directed to the modified natural product having a melting point of 40 °C or more), this invention has been constructively elected by original presentation for prosecution on the merits. Accordingly, the species “does not have a melting point” has been withdrawn from consideration as being directed to a non-elected invention. See 37 CFR 1.142(b) and MPEP § 821.03.
To preserve a right to petition, the reply to this action must distinctly and specifically point out supposed errors in the restriction requirement. Otherwise, the election shall be treated as a final election without traverse. Traversal must be timely. Failure to timely traverse the requirement will result in the loss of right to petition under 37 CFR 1.144. If claims are subsequently added, Applicant must indicate which of the subsequently added claims are readable upon the elected invention.
Should Applicant traverse on the ground that the inventions are not patentably distinct, Applicant should submit evidence or identify such evidence now of record showing the inventions to be obvious variants or clearly admit on the record that this is the case. In either instance, if the examiner finds one of the inventions unpatentable over the prior art, the evidence or admission may be used in a rejection under 35 U.S.C. 103 or pre-AIA 35 U.S.C. 103(a) of the other invention.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 12 and 16-23 are rejected under 35 U.S.C. 103 as being unpatentable over Engelhardt et al. (US 2001/0007027; “Engelhardt”) in view of Adelman et al. (US 2022/0033531; “Adelman”) (both references previously cited).
Regarding claim 12, Engelhardt discloses a polysaccharide derivative wherein at least one hydroxyl (–OH) group of a polysaccharide or polysaccharide ether is substituted with a carbamic acid (–C(=O)-–NHR1–) wherein R1 is a linear or branched aliphatic chain having 1 to 18 carbon atoms [Abstract; 0001-0002, 0030-0033, 0036-0038]. The polysaccharide or ether thereof is suitably cellulose or a cellulose ether, respectively, said cellulose ether exemplified by hydroxypropyl cellulose or hydroxyethyl cellulose [0025-0026, 0032, 0038, 0041, 0044].
The polysaccharide or polysaccharide ether (hereinafter “polysaccharide/ether”) is refluxed in a suspending medium/solvent such as dimethylformamide, dioxane, or toluene [0041, 0045]; a catalyst such as an amine or an organotin compound is added thereto [0041, 0047], followed by addition of an isocyanate compound such as octadecyl isocyanate (C18 hydrocarbon chain) or dodecyl isocyanate (C12 hydrocarbon chain) [0041, 0046, 0063] (see MPEP 2131.02(II)). The isocyanate compound reacts with the hydroxyl group(s) (hydrogen atoms thereof) of the polysaccharide/ether, resulting in the polysaccharide derivative (substitution of the hydroxyl group(s) with the carbamic acid) referred to as a urethane derivative of polysaccharide or urethane derivative of polysaccharide ether, alternatively “polysaccharide urethane” or “polysaccharide ether urethane” [0038-0042, 0053, 0063] (hereinafter “polysaccharide/ether urethane”).
The degree of substitution of the polysaccharide/ether urethane, per anhydroglucose unit, is suitably DS 0.3 to 3.0 [0038], e.g. DS of 1.3 [0063]. DS of 3.0 is 100% substitution of the (three) hydroxyl groups of the anhydroglucose unit; DS of 1.3 is about 43% substitution of said hydroxyl groups; DS of 0.3 is 10% substitution of said hydroxyl groups.
Engelhardt discloses that the polysaccharide derivative is suitable for the production of coatings, fibers, and films, and may be combined with additives [0054].
It is noted that Applicant’s spec indicates that the “oil-resistant agent” is prepared by reaction of, e.g. cellulose (natural product) with octadecyl isocyanate in (reflux) dimethylformamide solvent, catalyzed by dibutyltin dilaurate [0205 – Example 1], or, e.g. hydroxypropyl cellulose with octadecyl isocyanate in chloroform solvent, catalyzed by dibutyltin dilaurate [0206 – Example 2]. Generally, the spec indicates that the natural product is suitably cellulose (polysaccharide) or a cellulose derivative such as hydroxypropyl cellulose or hydroxyethyl cellulose [0095, 0097, 0100-0104]; the hydroxyl group(s) of the natural product are reacted with a modifying agent, e.g. an aliphatic isocyanate in an organic solvent in the presence of a catalyst such as tin catalyst or an amine [0111-0112, 0116-0118]. Suitable isocyanates include dodecyl isocyanate and octadecyl isocyanate [0119, 0205-0206].
In view of the foregoing, the polysaccharide derivatives, i.e. polysaccharide/ether urethanes of Engelhardt read on the oil-resistant agent defined by claim 12. The carbamic acid group, exemplified by (–C(=O)-–NHR1–) wherein R1 is a C1 to C18 hydrocarbon chain – and in particular a C12 or C18 carbon chain as set forth/cited above – which replaces the hydrogen atom of the hydroxyl group(s) of the polysaccharide/ether, reads on the claimed R group represented by –Y–Z; specifically, reads on the claimed R group wherein Y is –C(=O)–NR’– wherein R’ is a hydrogen atom, and wherein Z is an optionally-substituted hydrocarbon group having 7 to 40 carbon atoms. That is, the polysaccharide/ether urethane of Engelhardt formed from octadecyl isocyanate exhibits 18 carbon atom R1 chain length, and the polysaccharide/ether urethane formed from dodecyl isocyanate exhibits 12 carbon atom R1 chain length, each of which are within the claimed range of 7 to 40 carbon atoms (see MPEP 2131.03). The polysaccharide/ether urethanes of Engelhardt are not formed from starch, and thereby read on the negative claim limitation “wherein the natural product is a natural product other than starch”. The polysaccharide being a cellulose or cellulose ether reads on claimed provisos (1) and (2) of the “wherein at least one of (1) to (3) is satisfied”.
The polysaccharide/ether urethanes of Engelhardt, which are substantially identical or identical to the claimed and disclosed oil-resistant agent in terms of material/chemical components/compounds (natural product species; e.g. hydroxypropyl cellulose, cellulose; isocyanate species, e.g. dodecyl isocyanate, octadecyl isocyanate) and process of making (solvent type/species, catalyst type/species), would have necessarily exhibited at least some degree of oil resistance, absent a showing of factually supported objective evidence to the contrary (see MPEP 2112(V); MPEP 2112.01(I) and (II); MPEP 2145(I)). As such, the polysaccharide/ether urethanes of Engelhardt read on the nominal phrase “oil-resistant” of the “oil-resistant agent” as recited in the preamble of claim 12.
Engelhardt is silent regarding the polysaccharide/ether urethanes being attached to a textile product which is a paper product.
Adelman is directed to polysaccharide derivatives comprising a polysaccharide which is substituted (at least one hydroxyl group thereof) with at least one carbamate (carbamic acid) group derived from an aliphatic mono-isocyanate, e.g. octadecyl isocyanate and has a degree of substitution DS of 0.001 to about 3 [Abstract; 0001, 0003, 0008-0010, 0012, 0025, 0037, 0048, 0051, 0054]. The polysaccharide derivative is suitably prepared by contacting the polysaccharide with the isocyanate in a solvent, e.g. dimethylformamide [0068]. Adelman teaches that the polysaccharide derivative – in addition to forming films or fibers – can be included/dispersed in aqueous (water-based) dispersions or aqueous formulations to form water-based paints and water-based inks [0077-0079, 0081, 0085-0087, 0099, 0188], and/or for coating fabrics, e.g. textiles and nonwovens (in the form of aqueous textile/fabric or laundry care compositions), and/or for coating paper substrates, to improve liquid impermeability or comfort thereof; the foregoing applications are also applicable wherein the dispersions/formulations are (organic) solvent-based [0038-0040, 0042-0043, 0079, 0081, 0087-0088, 0090-0091, 0131, 0191-0192].
Engelhardt and Adelman each constitute prior art which is directly analogous to the claimed invention. In view of the combined teachings of the foregoing prior art, it would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to have modified the polysaccharide/ether urethanes of Engelhardt by (1) dispersing one or more thereof in an aqueous composition/dispersion to form a water-based paint, ink, fabric/textile care composition, or paper-coating composition, as the polysaccharide/ether urethanes would have been readily recognized as suitable for the (aforesaid) intended uses (see MPEP 2144.07), and by (2) coating the polysaccharide/ether urethanes – as-is, or in the form of the aqueous dispersion, or in the form of a solvent-based composition/dispersion – onto paper substrate (textile product, which is a paper product), in order to impart liquid impermeability thereto, and/or because the polysaccharide/ether urethanes would have been readily recognized as suitable for (the intended use of) coating the aforesaid paper substrate for the purpose of imparting said impermeability thereto (see MPEP 2144.07).
In accordance with the foregoing modification(s), the polysaccharide/ether urethanes of Engelhardt (hereinafter “modified Engelhardt”) would have been dispersed or otherwise included in an aqueous dispersion/composition, and thereafter would have been coated on a surface of a paper product/substrate, as-is or in the form of an aqueous or solvent-based dispersion/composition. The paper substrate/product of modified Engelhardt, having the polysaccharide/ether urethanes coated thereon (to which an oil-resistant agent is attached), read on the textile product to which an oil-resistant agent is attached defined by claim 12.
Regarding claim 16, the rejection of claim 12 above reads on the textile product defined by claim 16 – the polysaccharide or polysaccharide ether of modified Engelhardt, e.g. cellulose or hydroxypropyl cellulose, reads on the “compound of a natural product as is” and “compound derived from a natural product”, respectively. As noted above, the spec indicates that the natural product may be cellulose, and the compounds derived from the natural product may be cellulose ethers such as hydroxypropyl and hydroxyethyl cellulose.
Regarding claim 17, the rejection of claim 12 above reads on the textile product defined by claim 17 (the high-molecular-weight natural product is cellulose).
Regarding claim 18, the rejection of claim 12 above reads on the textile product defined by claim 18 – the DS of the polysaccharide/ether urethanes of modified Engelhardt suitably ranges from 0.3 to 3.0, i.e. 10% to 100% substitution of the (three) hydroxyl groups of the polysaccharide or polysaccharide ether, of which is within the range of 3 to 100% (MPEP 2131.03). Additionally/alternatively, Engelhardt discloses a preferred DS range of 0.6 to 2.5 [0038], i.e. 20% to about 83% which is within the claimed range.
Regarding claim 19, the rejection of claim 12 above (see ¶18) reads on the textile product defined by claim 19. R’ of the polysaccharide/ether urethanes of modified Engelhardt is a hydrogen atom, and Z is an aliphatic hydrocarbon having 1 to 18 carbon atoms, e.g. 12 carbon atoms in the case of dodecyl isocyanate, e.g. 18 carbon atoms in the case of octadecyl isocyanate (see MPEP 2144.05(I)).
Regarding claim 20, as set forth above in the rejection of claim 12, the polysaccharide/ether urethane of modified Engelhardt is substantially identical to the claimed and disclosed oil-resistant agent in terms of material/chemical components/compounds (natural product species, e.g. hydroxypropyl cellulose, cellulose; isocyanate species, e.g. dodecyl isocyanate, octadecyl isocyanate) and process of making (solvent type/species, catalyst type/species), as well as in terms of the range of DS of the hydroxyl group of the polysaccharide/ether urethane (including up to 100%), and the melting temperature exhibited by the polysaccharide/ether urethane (e.g. 200° C exhibited by Example 3). In view thereof, it stands to reason that the polysaccharide/ether urethane(s) of modified Engelhardt, and/or the polysaccharide ether urethane of Example 3 of modified Engelhardt, would have necessarily exhibited an n-hexadecane contact angle of 10° or more as claimed, absent a showing of factually supported objective evidence to the contrary. See MPEP 2112(IV) and (V); MPEP 2112.01(I) and (II); MPEP 2145; and MPEP 2145(I).
Regarding claim 21, as set forth/cited above in the rejection of claim 12, as well as the rejection of claim 18 above, Engelhardt discloses the polysaccharide ether urethane of Example 3 [0063], formed from hydroxypropyl cellulose and dodecyl isocyanate, which exhibits a melting temperature of 200° C, of which is within the claimed range of melting point of 40° C or more (MPEP 2131.03).
Additionally/alternatively, the rejection of claim 20 set forth above (¶28) is incorporated herein by reference and reads on the textile product defined by claim 21. That is, the polysaccharide/ether urethanes of modified Engelhardt would have necessarily exhibited a melting point of 40° C or greater, absent a showing of factually supported objective evidence to the contrary. See MPEP 2112(IV) and (V); MPEP 2112.01(I) and (II); MPEP 2145; and MPEP 2145(I).
Regarding claim 22, in view of the rejection of claim 12 above, the rejection of claim 20 above (¶28) is incorporated herein by reference and reads on the textile product defined by claim 22. That is, the polysaccharide/ether urethanes of Engelhardt, and/or the polysaccharide ether urethane of Example 3 of Engelhardt, would have necessarily exhibited a viscosity of 5 to 100 cP at a solution concentration of 14.8 mg/mL, absent a showing of factually supported objective evidence to the contrary. See MPEP 2112(V); MPEP 2112.01(I) and (II); MPEP 2145; and MPEP 2145(I).
Regarding claim 23, the rejection of claim 12 above reads on the textile product defined by claim 23.
Response to Arguments
Applicant’s arguments presented on pp. 7-8 of the Remarks filed 26 February 2026 have been fully considered but not found persuasive.
Applicant asserts (1) that the materials (polysaccharide derivatives) of Engelhardt are thermoplastically processable, which is fundamentally different from the requirements of paper coatings, and that Engelhardt neither teaches nor suggests that the materials could be applied to a paper substrate without destroying the structural/functional properties. However, Engelhardt explicitly teaches that the materials are suitable for the production of coatings [0054]. Further, the prima facie case of obviousness established in the rejection is not based solely on the disclosure of Engelhardt, but rather, the combination of the disclosure of Engelhardt taken in view of the teachings of Adelman, i.e. that the polysaccharide derivatives are suitable for forming aqueous or solvent-based coating compositions for paper products. As such, Applicant is respectfully directed to MPEP 2145(IV) – one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. “The test for obviousness is what the combined teachings of the references would have suggested to a person having ordinary skill in the art”. For these reasons, Applicant’s argument has not been found persuasive.
Applicant asserts (2) that Adelman does not teach or suggest application (of the polysaccharide derivatives) to paper or paper products, or modification of paper to impart oil resistance, citing to [0077-0079]. However, it is noted that the disclosure/teachings of Adelman cited and relied upon in the grounds of rejection establishing the prima facie case of obviousness are not limited to [0077-0079], but rather, include [0191-0192] (see ¶21 above), wherein Adelman explicitly teaches that the polysaccharide derivatives can be used to coat paper substrates. For these reasons, and in light of MPEP 2145(IV) noted above, Applicant’s argument has not been found persuasive.
Applicant then asserts (3), in a single sentence, that the claimed product “exhibits unexpectedly superior oil resistance when applied to paper substrates”, citing to the specification [0012, Examples]; (4) followed by an assertion that one of ordinary skill in the art would not reasonably expect thermoplastic compositions designed for molded bulk articles to provide oil resistance. Thereafter, Applicant asserts (5) that there would not have been a reasonable expectation of success in achieving oil resistance in a paper product without “compromising its fundamental characteristics”. However, (5) Applicant does not specifically identify any one or more of said fundamental characteristics which would have been compromised; (4) has not provided any technical reasoning/explanation, or supporting objective evidence, as to why one of ordinary skill in the art would not have reasonably expected the polysaccharide derivatives of (modified) Engelhardt to provide oil resistance; and (3) has not met the burden of explaining how/why the asserted oil resistance is unexpected (see MPEP 716.02(b)(I) and (b)(II)). In totality, Applicant’s assertions (3)-(5) constitute mere conclusory statements which are not supported by objective evidence and/or technical reasoning necessary to rebut the prima facie case of obviousness and/or establish, in fact, that the results are unexpected. For these reasons, Applicant’s arguments have not been found persuasive.
Pertinent Prior Art
The following constitutes a list of prior art which are not relied upon herein, but are considered pertinent to the claimed invention and/or written description thereof. The prior art are purposely made of record hereinafter to facilitate compact/expedient prosecution, and consideration thereof is respectfully suggested.
EP 0157365 B1 to Okamoto et al. (copy provided herewith) – discloses carbamate derivatives of polysaccharides [p. 2 ln. 39–p. 10]
US 6,362,330 to Simon et al. – discloses polysaccharide-based thermoplastic materials suitable for coatings [Abstract; cols. 1, 4-6, 9]
Conclusion
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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/MICHAEL C. ROMANOWSKI/Primary Examiner, Art Unit 1782
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