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.
Election/Restrictions
Applicant’s election without traverse of Invention I, claims 1-14; Species I-A, claim 8 – melting point of 40° or more; and Species II-A, claim 12, in the reply filed on 28 October 2025 is acknowledged.
Claims 13-14 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species, there being no allowable generic or linking claim. Claim 15 is withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Information Disclosure Statement
The information disclosure statements (IDS) filed 22 March 2023, 04 May 2023, 13 July 2023, 27 October 2023, 21 December 2023, 17 June 2024, 27 December 2024, 06 February 2025, and 06 March 2025 are in compliance with 37 CFR 1.97 and have been considered.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
Claim 8 is 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.
Regarding claim 8, the recitation of the modified natural product having a melting point of “40 degrees” renders the claim indefinite – the temperature scale is unclear/ambiguous due to the absence of a corresponding unit, e.g. Fahrenheit, Kelvin, or Celsius.
In order to overcome the indefiniteness issue, the following amendment is respectfully suggested; “…has a melting point of 40° C or more”, of which finds explicit support in the specification [0168]. For examination on the merits, claim 8 is interpreted in accordance with the suggested amendment, i.e. interpreted where the temperature unit is Celsius.
Appropriate action is required.
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.
Claim 6 is rejected under 35 U.S.C. 112(d) as being of improper dependent form for failing to include all the limitations of the claim upon which it depends.
Regarding claim 6, the recitation of “wherein Z is an optionally-substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms…” fails to include all of the limitations of claim 1, which recites that the optionally-substituted hydrocarbon group has 7 to 40 carbon atoms.
In order to overcome the 112(d) issue, it is respectfully suggested to amend claim 6 as follows: “…having [[1]]7 to 40 carbon atoms”. For examination on the merits, claim 6 is interpreted in accordance with the suggested amendment, i.e. where the hydrocarbon group is limited to 7 to 40 carbon atoms.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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.
Claims 1-9 and 11 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Engelhardt et al. (US 2001/0007027; “Engelhardt”).
Regarding claim 1, 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 anticipates the oil-resistant agent defined by each and every limitation of claim 1. 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 anticipate the negative claim limitation “wherein the natural product is a natural product other than starch”.
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/anticipate the nominal phrase “oil-resistant” of the “oil-resistant agent” as recited in the preamble of claim 1.
Regarding claim 2, the grounds of rejection of claim 1 above read on the agent defined by claim 2 – the polysaccharide or polysaccharide ether of Engelhardt, e.g. cellulose or hydroxypropyl cellulose, read on the “compound of a natural product as is” and “[or a] 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 3, the grounds of rejection of claim 1 above read on the agent defined by claim 3 – cellulose and cellulose ether(s) are polysaccharides, as evident from the disclosure of Engelhardt, also evidenced by Applicant’s spec [0100], and readily understood by one of ordinary skill in the art.
Regarding claim 4, the grounds of rejection of claim 1 above read on the agent defined by claim 4, specifically, at least the high-molecular weight natural product species “cellulose”.
Regarding claim 5, the grounds of rejection of claim 1 above read on the agent defined by claim 5 – the DS of the polysaccharide/ether urethanes of 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. Additionally/alternatively, Engelhardt discloses an example wherein the polysaccharide ether urethane, formed from hydroxypropyl cellulose and dodecyl isocyanate, exhibits a DS of 1.3 [0063 – Example 3], i.e. about 43% which is within the claimed range.
Regarding claim 6, the grounds of rejection of claim 1 above read on the agent defined by claim 6 – see ¶24 above.
Regarding claim 7, as set forth above in the grounds of rejection of claim 1, the polysaccharide/ether urethane of 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 Engelhardt, and/or the polysaccharide ether urethane of Example 3 of 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(V); MPEP 2112.01(I) and (II); MPEP 2145; and MPEP 2145(I).
Regarding claim 8, as set forth/cited above in the grounds of rejection of claim 1, as well as the grounds of rejection of claim 5 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 grounds of rejection of claim 7 set forth above (¶31) are incorporated herein by reference and read on the agent defined by claim 8. That is, the polysaccharide/ether urethanes of 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(V); MPEP 2112.01(I) and (II); MPEP 2145; and MPEP 2145(I).
Regarding claim 9, in view of the grounds of rejection of claim 1 above, the grounds of rejection of claim 7 above (¶31) are incorporated herein by reference and read on the agent defined by claim 9. 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 11, it is noted that claim 11, which is a product claim and directly dependent upon claim 1, recites in the body thereof “which is for paper”. The aforesaid recitation does not define how, or in what form, the oil-resistant agent is configured “for paper”. As such, the recitation is analogous to a recitation [in the preamble of a claim] of the purpose or intended use of the invention, rather than a distinct definition of the claimed invention’s limitations (see MPEP 2111.02(II))
In the instant case, the recitation in claim 11 does not appear to result in a structural difference between the claimed invention and the polysaccharide/ether urethanes of Engelhardt, given that specific limitations regarding the oil-resistant agent itself are not recited (MPEP 2111.02(II)). Furthermore, Engelhardt discloses that the polysaccharide/ether urethanes are thermoplastically-processible, e.g. may be extruded/molded or otherwise formed into films, and may also take the form of coatings (i.e. may be coated on surfaces/substrates) [0001, 0052-0054]. Given that there is no structural, chemical, or material difference between the polysaccharide/ether urethanes of Engelhardt and the oil-resistant agent defined by claim 11, and given that the polysaccharide/ether urethanes of Engelhardt are thermoplastically-processible and/or may be coated onto other surfaces/substrates, it stands to reason that the polysaccharide/ether urethanes would be readily, and necessarily, capable of use with/for paper (capable of performing the intended use), as recited in claim 11. As such, the polysaccharide/ether urethanes of Engelhardt set forth above read on the oil-resistant agent defined by claim 11.
Claim Rejections - 35 USC § 103
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.
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.
Claims 10 and 12 are rejected under 35 U.S.C. 103 as being unpatentable over Engelhardt as applied to claim 1 under 35 U.S.C. 102(a)(1) above, further in view of Adelman et al. (US 2022/0033531; “Adelman”).
Regarding claims 10 and 12, in view of the grounds of rejection of claim 1 under 35 U.S.C. 102(a)(1) above, Engelhardt is silent regarding the polysaccharide/ether urethanes being included in or forming a water-dispersion composition (claim 10), and regarding the polysaccharide/ether urethanes being attached to a textile product (claim 12).
Adelman is directed to polysaccharide derivatives comprises 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/or 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 a fabric or textile substrate, or paper substrate, in order to impart liquid impermeability thereto, comfort thereto, and/or because the polysaccharide/ether urethanes would have been readily recognized as suitable for (the intended use of) coating the aforesaid substrates, e.g. textiles for the purpose of imparting the aforesaid properties/qualities thereto (see MPEP 2144.07).
In accordance with the aforesaid modification (1), the polysaccharide/ether urethanes of Engelhardt would have been dispersed or otherwise included in an aqueous dispersion/composition, thereby reading on the oil-resistant agent defined by claim 10, i.e. “a water dispersion composition”. In accordance with the aforesaid modification (2), in view of (1) or independently of (1), the polysaccharide/ether urethanes of Engelhardt would have been coated on a surface of a textile/fabric product, as-is or in the form of an aqueous or solvent-based dispersion/composition, to treat or form a coating on said surface, thereby reading on the textile product defined by claim 12, i.e. “A textile product to which the oil-resistant agent according to claim 1 is attached”.
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.
JP 3587803 B2 to Hatanaka et al. (copy and machine translation provided herewith) – discloses water-repellent treatment of cellulosic fiber materials comprising treating cellulose, in a solvent such as dimethylformamide and in the presence of a tin-based or amine-based catalyst, with a compound having one or more isocyanate groups, e.g. octadecyl isocyanate that reacts with the hydroxyl group(s) of the cellulose to impart hydrophobicity thereto [pp. 1-4]; the water-repellent treatment is suitable for treating natural fibers such as cotton and hemp, and fibrous materials including fabrics and nonwovens [p. 9]
JPH11-302301 A to Yamawaki et al. (copy and machine translation provided herewith) – discloses cellulose compounds comprising the addition or graft polymerization of silane coupling agents to the functional groups of cellulose derivatives (which form siloxanes through condensation cure), said compounds suitable for use as impregnating agents for paper [0015-0016, 0020-0037, 0040]; the cellulose derivatives are suitably obtained from natural polysaccharides such as mannan, galactan, araban, xylan, or pectin [0039]; the cellulose compounds exhibit a DS of 2.0 to 2.7 [0043]; the reaction is carried out in solvent such as dimethylformamide in the presence of a catalyst such as an amine [0048]
Conclusion
Any inquiry concerning this communication or earlier communications from the Examiner should be directed to Michael C. Romanowski whose telephone number is (571)270-1387. The Examiner can normally be reached M-F, 09:30-17:30.
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If attempts to reach the Examiner by telephone are unsuccessful, the Examiner’s supervisor, Aaron Austin can be reached at (571) 272-8935. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/MICHAEL C. ROMANOWSKI/Primary Examiner, Art Unit 1782
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