DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 9/22/2025 has been entered.
Claims 1, 4-12, 16-17, 19-25 and 28-32 are pending as amended on 9/22/2025.
Claims 1, 4-12, 16 and 28 stand withdrawn from consideration.
Any rejections and/or objections made in the previous Office action and not repeated below are hereby withdrawn. The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office Action.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 17, 19-25 and 29-32 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
Claim 17 has been amended to require that the two-dimensional material exhibits an N-H stretching frequency of about 3213 cm-1 and/or a C=O stretching frequency of about 1601 cm-1, as determined by FTIR spectroscopy.
An FTIR spectrum of a material wherein the newly recited stretching frequencies are labeled is shown in figure 3D of the specification as originally filed. However, figure 3D shows an FTIR spectrum of a material having a specific chemical structure (i.e., a polymer formed from trimesoyl chloride and melamine) and having specific % transmittances at stretching frequencies of 3213 cm-1 and 1601 cm-1. In contrast, the present claims are not limited to a polymer formed from trimesoyl chloride and melamine, and/or, not limited to polymers which exhibit the particular % transmittance at frequencies of 3213 cm-1 and 1601 cm-1 which are shown in Figure 3D. Additionally, in view of the claim language “about,” the claim encompasses materials exhibiting a stretching frequency within a range which encompasses values above and below 3213 cm-1, and above and below 1601 cm-1. There is no support in the specification as filed for reciting a range of stretching frequencies as implied by the use of the term “about.” For at least these reasons, the claims as presently drafted are not commensurate in scope with the limited support provided by the examples of the specification, and therefore Applicant has not demonstrated that the inventor, at the time the application was filed, had possession of materials within the full scope of claim 17 (and claims which depend from claim 17).
New independent claim 32 is similar to independent claim 17, except that the claim recites a weight loss of no more than 5% at 312 C instead of reciting FTIR stretching frequencies. The limitation is also found in new dependent claim 31. A TGA of a specific material (YZ-2) which has a 5% weight loss at 312 C is shown in instant figure 26 C. However, YZ-2 has a specific structure (formed from reaction of trimesoyl chloride and melamine) and is formed using specific process conditions (in NMP, using CaCl2 and pyridine; see Figure 26B). In contrast, the present claims are not limited to a polymer formed from trimesoyl chloride and melamine, and are not limited to any particular method of making. Moreover, claims 31 and 32 recite a weight loss of no more than 5%, which encompasses materials having, e.g., 0% weight loss at 312 C. There is no description in the specification as filed of any material having less than 5% weight loss at 312 C. For at least these reasons, the claims as presently drafted are not commensurate in scope with the limited support provided by the examples of the specification, and therefore Applicant has not demonstrated that the inventor, at the time the application was filed, had possession of materials within the full scope of claims 31 and 32.
Additionally: new claim 29 recites a material made by a method wherein contacting of monomers takes place in a solvent which comprises a combination of six different solvents and salt solutions thereof. The claim does not recite the solvents in the alternative, and therefore requires a material made by a method wherein each of the recited solvents must be present. There is no description in the specification as filed of a process which utilizes a combination of all of the solvents recited in new claim 29. Therefore, Applicant has not demonstrated that the inventor, at the time the application was filed, had possession within the full scope of claim 29 (and claim 30, which depends from claim 29). See MPEP 2173.05(h) for guidance on constructing claims which recite a list of alternatives to define a limitation.
Claim Rejections - 35 USC § 102
Claim(s) 17, 19-25 and 29-32 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Shao et al (One-pot synthesis of melamine-based porous polyamides for CO2 capture, Microporous and Mesoporous Materials 285 (2019) 105–111; Available online 5/7/2019). A copy of the supplementary materials associated with Shao, cited below, is included within this action.
As to claims 17 and 19-25, Shao discloses (p 106):
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The material “TMPA” disclosed by Shao has a structure as shown in instant claim 25, and therefore, Shao discloses a material comprising a two-dimensional polymer which meets the recitations of instant claims 17 and 19-25. Given that Shao discloses a TMPA polymer from the same monomers as used to form the presently recited polymer shown in claim 25 (melamine and trimesic acid), and given that the hydrogens in the amide groups of Shao’s polymer must be capable of participating in hydrogen bonding with the oxygen or nitrogen atoms of another TMPA polymer, there is reasonable basis to conclude that the TMPA material disclosed by Shao forms at least some amount of hydrogen bonds in a third dimension as presently recited.
As to the recited stretching frequencies, Shao provides an FTIR spectrum of TMPA (see supplementary materials, p 4) which shows that TMPA exhibits stretching at a frequency of about 3213 cm-1 and about 1601 cm-1 (see below, annotated by the Examiner with lines to show approximate location of about 3213 cm-1 and about 1601 cm-1.
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As to claims 29 and 30, Shao discloses a method of preparing TMPA by contacting monomers in DMSO as solvent. See scheme 1. Shao fails to teach utilizing a combination of solvents as recited in claims 29 and 30.
Claims 29 and 30 are product-by-process claims. Case law has established that the patentability of a product-by-process is determined by the patentability of the product itself, i.e., that the patentability of a product does not depend upon its method of production (MPEP 2113). The process limitations are only given consideration regarding patentability if there is criticality to the structure implied by the steps of the process. Because the claims as presently drafted do not contain any limitations which materially distinguish the presently claimed material from the TMPA of Shao, it is evident that the material which is presently claimed is met by Shao’s TMPA, notwithstanding any difference in the method by which the TMPA of Shao is made.
As to claims 31 and 32, Shao fails to teach a TGA weight loss of no more than 5% at 312 C. However, given that Shao discloses a polymer (TMPA) which has the same structure as the polymer YZ-2 shown in instant figure 26B, there is reasonable basis to conclude that when analyzed utilizing the same sample preparation and under the same TGA conditions, Shao’s TMPA would exhibit substantially the same weight loss properties as instant YZ-2 shown in instant figure 26C (i.e., a TGA weight loss of 5% at 312 C).
Claim(s) 17, 19-25 and 29-32 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Zulfiqar et al (Melamine based porous organic amide polymers for CO2 capture, RSC Adv., 2014, 4, 52263–52269).
As to claims 17 and 19-25, Zulfiqar discloses amide polymers formed from reaction of melamine with 1,3,5-benzenetricarbonyl trichloride (trimesoyl chloride) in a solvent mixture of DMAc and NMP (“PA-1;” See scheme 1 on p 52265, and p 52264, section 2.3):
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Zulfiqar teaches that PA-1 exhibits increased crystallinity as a result of employing DMAc-NMP as the solvent system (p 52265, 3.1; p 52268, conclusion).
Zulfiqar fails to specifically define PA-1 as a “two dimensional polymer,” and fails to include sufficient units in the structure drawing copied above to show a structure that matches the structure shown in instant claim 25.
However, Zulfiqar discloses a polymer formed from the same monomers as disclosed in the instant specification (see p 16) for providing a 2D polymer as shown in instant claim 25. Furthermore, according to the instant specification, solvent is important to control material properties, and high polar solvents with strong hydrogen bond acceptor ability are favored. The instant specification names NMP as an example of such a solvent (p 19, lines 7-10). DMAc (the other solvent utilized by Zulfiqar in combination with NMP) is similarly polar and has hydrogen bond acceptor ability. Given that polymers produced from the same reactants under substantially similar reaction conditions must have substantially similar chemical structures, there is reasonable basis to conclude that the PA-1 polymer formed from reaction of 1,3,5-benzenetricarbonyl trichloride and melamine in NMP and DMAc, as disclosed by Zulfiqar, has substantially the same structure as the presently claimed and described polymer formed from benzenetricarbonyl trichloride and melamine in NMP. There is reasonable basis to conclude, therefore, that Zulfiqar discloses a material (PA-1) which comprises a two dimensional rigid structure with at least some ordered hydrogen bonds in a third dimension, as recited in the present claims, and which includes a structure as shown in instant claim 25.
As to the recitation that the material exhibits an N-H stretching frequency of about 3213 cm-1 and/or a C=O stretching frequency of about 1601 cm-1, as determined by FTIR spectroscopy: Zulfiqar discloses an N-H stretch at 3307 cm-1, which meets the presently recited “about 3213 cm-1,” and discloses C=O stretch at 1644-1666 cm-1, which meets the presently recited “about 1601 cm-1.” See p 52264, lower right.
As to claims 29 and 30, Zulfiqar discloses a method of preparing PA-1 by reacting benzenetricarbonyl trichloride and melamine in solvent comprising NMP. See scheme 1. Zulfiqar fails to teach utilizing a combination of solvents as recited in claims 29 and 30.
Claims 29 and 30 are product-by-process claims. Case law has established that the patentability of a product-by-process is determined by the patentability of the product itself, i.e., that the patentability of a product does not depend upon its method of production (MPEP 2113). The process limitations are only given consideration regarding patentability if there is criticality to the structure implied by the steps of the process. Because the claims as presently drafted do not contain any limitations which materially distinguish the presently claimed material from the PA-1 of Zulfiqar, it is evident that the material which is presently claimed is met by Zulfiqar’s PA-1, notwithstanding any difference in the method by which the PA-1 of Zulfiqar is made.
As to claims 31 and 32, Zulfiqar fails to teach a TGA weight loss of no more than 5% at 312 C. However, given that Zulfiqar discloses a polymer (PA-1) which has the same structure as the polymer YZ-2 shown in instant figure 26B, there is reasonable basis to conclude that when analyzed using the same sample preparation and under the same TGA conditions, Zulfiqar’s PA-1 would exhibit substantially the same weight loss properties as instant YZ-2 shown in instant figure 26C (i.e., a TGA weight loss of 5% at 312 C).
Claim Rejections - 35 USC § 103
Claim(s) 17, 19-25 and 29-32 is/are rejected under 35 U.S.C. 103 as being unpatentable over Shao et al (One-pot synthesis of melamine-based porous polyamides for CO2 capture, Microporous and Mesoporous Materials 285 (2019) 105–111; Available online 5/7/2019; a copy of the supplementary materials associated with Shao, cited below, is included within this action) in view of Rosado et al (High strength films from oriented, hydrogen-bonded “graphamid” 2D polymer molecular ensembles. Sci Rep 8, 3708 (2018)) and Wetzel et al (US 2017/0240706).
As to claims 17 and 19-25, Shao discloses (p 106):
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The material “TMPA” disclosed by Shao has the same chemical structure shown in instant claim 25, and therefore meets the chemical structure recited in instant claims 17 and 19-25.
As to the recited stretching frequencies, Shao provides an FTIR spectrum of TMPA (see supplementary materials, p 4) which shows that TMPA exhibits stretching at a frequency of about 3213 cm-1 and about 1601 cm-1 (see below, annotated by the Examiner with lines to show approximate location of about 3213 cm-1 and about 1601 cm-1.
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Shao discloses that polyamides are one of the first engineering thermoplastics and are extensively employed due to their combination of high thermal stability, good chemical resistance and excellent mechanical properties, which are mainly attributed to the strong intermolecular associations of polyamides and rigid structure (p 105, lower left). However, Shao fails to specifically characterize the TMPA shown above as being a “two dimensional polymer” and fails to teach that TMPA forms ordered hydrogen bonds in a third dimension.
Rosado discloses that poly(p-phenylene terephthalamide) (PPTA, a linear commercially available polyamide known as Kevlar) is an icon of modern materials science due to its remarkable strength, stiffness and environmental resistance (abstract). Rosado teaches that PPTA performance is enabled by its rigid aromatic backbone and strong intermolecular hydrogen bonding (p 1, third paragraph). Rosado teaches a two-dimensional (2D) polymer (graphamid) that resembles Kevlar in chemical structure but is mechanically advantaged by virtue of its 2D structure (abstract). The 2D nature of graphamid gives it strength and stiffness in all in-plane directions, unlike in linear PPTA (p 2, first four lines). Rosado teaches that the presence of hydrogen bonds that bridge molecular planes provides significant benefits in terms of strength and stiffness in molecular ensembles (p 6).
Similarly, Wetzel also discloses 2D polymer compounds that have continuous bond networks that extend in all directions in the material plane, so that they can demonstrate high stiffness and strength in all directions [0029]. Wetzel similarly teaches that the 2D polymers are able to be stacked into ordered ensembles (abstract), and that the 2D polymer composition may exhibit inter-molecular hydrogen bonding [0029] (i.e., are capable of inter-molecular hydrogen bonding to other similar 2D polymer molecules, see claim 12 of Wetzel). Wetzel teaches producing the 2D polymers using a step-growth approach, wherein at least one monomer must have 3 or more functional groups. The greater the functionality of each molecule, the greater the crosslink density and smaller the pores of the resulting polymer [0086]. Wetzel teaches that the ability to create a tailored pore size and pore chemistry can result in very high selectivity in selective barriers [0118].
Wetzel teaches that producing graphamid (i.e., the 2D polymer disclosed in Rosado) that is analogous to graphene would require the use of hexaaminobenzene and benzene hexacarboxylic acid. To form similar 2D aromatic polyamides with a lower degree of crosslinking, Wetzel discloses three types of monomer combinations, including (as the third type) a combination of n-functional carboxylic acids/chlorides/esters with n≥3 and n-functional amines with n≥3 [0091]. [One having ordinary skill in the art would recognize from context that Wetzel’s disclosure of “n-functional diamines” and “n-functional dicarboxylic acids” in [0091] was meant to be a disclosure of polyamines and polycarboxylic acids.] Wetzel names useful polyamines which would result in all sp2 bonds through the backbone chains of the 2D polymer, including melamine [0092], and names useful carboxylic acids that would result in all sp2 bonds through the backbone chains of the 2D polymer, including trimesic acid [0093].
Considering the disclosures of Wetzel and Rosado regarding 2D polymers, one having ordinary skill in the art would have had a reasonable expectation of success in forming a 2D polymer from trimesic acid and melamine (because these are both monomers which are taught by Wetzel as forming sp2 bonds through the backbone of a 2D polymer), and, when forming a polyamide from trimesic acid and melamine having a structure as shown in Shao’s Scheme 1 (having bonds which extend in a 2D plane) the person having ordinary skill in the art would have been motivated to form a material which has intermolecular hydrogen bonding between layers (as taught by Rosado and Wetzel) in order to increase strength and stiffness of the material. It would have been obvious to the person having ordinary skill in the art, therefore, to have formed a material by reacting trimesic acid and melamine to provide a polymer having a structure according to TMPA, as shown by Shao in scheme 1, by forming the polymer as a two-dimensional material which has intermolecular hydrogen bonds (i.e., hydrogen bonds in a third dimension), as taught by Wetzel and Rosado, in order to provide a material having improved mechanical properties such as strength and stiffness.
As to claims 29 and 30, modified Shao suggests a material according to claims 17 and 25, as set forth above. Shao discloses a method of preparing TMPA by contacting monomers in DMSO as solvent. See scheme 1. Shao fails to teach utilizing a combination of solvents as recited in claims 29 and 30.
Claims 29 and 30 are product-by-process claims. Case law has established that the patentability of a product-by-process is determined by the patentability of the product itself, i.e., that the patentability of a product does not depend upon its method of production (MPEP 2113). The process limitations are only given consideration regarding patentability if there is criticality to the structure implied by the steps of the process. Because the claims as presently drafted do not contain any limitations which materially distinguish the presently claimed material from the material of modified Shao, it is evident that the material which is presently claimed is met by modified Shao, notwithstanding any difference in the method by which the material of modified Shao is made.
As to claims 31 and 32, Shao fails to teach a TGA weight loss of no more than 5% at 312 C. However, given that modified Shao suggests a polymer which has the same structure as the polymer YZ-2 shown in instant figure 26B, there is reasonable basis to conclude that when analyzed utilizing the same sample preparation and under the same TGA conditions, modified Shao suggests a material that would exhibit substantially the same weight loss properties as instant YZ-2 shown in instant figure 26C (i.e., a TGA weight loss of 5% at 312 C).
Claim(s) 17, 19-25 and 29-32 is/are rejected under 35 U.S.C. 103 as being unpatentable over Zulfiqar et al (Melamine based porous organic amide polymers for CO2 capture, RSC Adv., 2014, 4, 52263–52269) in view of Rosado et al (High strength films from oriented, hydrogen-bonded “graphamid” 2D polymer molecular ensembles. Sci Rep 8, 3708 (2018)) and Wetzel et al (US 2017/0240706).
As to claims 17 and 19-25, Zulfiqar discloses amide polymers formed from reaction of melamine with 1,3,5-benzenetricarbonyl trichloride in a solvent mixture of DMAc and NMP (“PA-1;” See scheme 1 on p 52265, and p 52264, section 2.3):
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Zulfiqar teaches that PA-1 exhibits increased crystallinity as a result of employing DMAc-NMP as the solvent system (p 52265, 3.1; p 52268, conclusion). As to the recitation that the material exhibits an N-H stretching frequency of about 3213 cm-1 and/or a C=O stretching frequency of about 1601 cm-1, as determined by FTIR spectroscopy: Zulfiqar discloses an N-H stretch at 3307 cm-1, which meets the presently recited “about 3213 cm-1,” and discloses C=O stretch at 1644-1666 cm-1, which meets the presently recited “about 1601 cm-1.” See p 52264, lower right.
Zulfiqar discloses that polyamides were the first engineering thermoplastics and have implausible thermal stability, good chemical resistance, marvelous mechanical properties. However, Zulfiqar fails to specifically characterize the PA-1 shown above as being a “two dimensional polymer” and fails to teach that PA-1 forms ordered hydrogen bonds in a third dimension.
Rosado discloses that poly(p-phenylene terephthalamide) (PPTA, a linear commercially available polyamide known as Kevlar) is an icon of modern materials science due to its remarkable strength, stiffness and environmental resistance (abstract). Rosado teaches that PPTA performance is enabled by its rigid aromatic backbone and strong intermolecular hydrogen bonding (p 1, third paragraph). Rosado teaches a two-dimensional (2D) polymer (graphamid) that resembles Kevlar in chemical structure but is mechanically advantaged by virtue of its 2D structure (abstract). The 2D nature of graphamid gives it strength and stiffness in all in-plane directions, unlike in linear PPTA (p 2, first four lines). Rosado teaches that the presence of hydrogen bonds that bridge molecular planes provides significant benefits in terms of strength and stiffness in molecular ensembles (p 6).
Similarly, Wetzel also discloses 2D polymer compounds that have continuous bond networks that extend in all directions in the material plane, so that they can demonstrate high stiffness and strength in all directions [0029]. Wetzel teaches that the 2D polymers are able to be stacked into ordered ensembles (abstract), and that the 2D polymer composition may exhibit inter-molecular hydrogen bonding [0029] (i.e., are capable of inter-molecular hydrogen bonding to other similar 2D polymer molecules, see claim 12 of Wetzel). Wetzel teaches producing the 2D polymers using a step-growth approach, wherein at least one monomer must have 3 or more functional groups. The greater the functionality of each molecule, the greater the crosslink density and smaller the pores of the resulting polymer [0086]. Wetzel teaches that the ability to create a tailored pore size and pore chemistry can result in very high selectivity in selective barriers [0118].
Wetzel teaches that producing graphamid (i.e., the 2D polymer disclosed in Rosado) that is analogous to graphene would require the use of hexaaminobenzene and benzene hexacarboxylic acid. To form similar 2D aromatic polyamides with a lower degree of crosslinking, Wetzel discloses three types of monomer combinations, including (as the third type) a combination of n-functional carboxylic acids/chlorides/esters with n≥3 and n-functional amines with n≥3 [0091]. [One having ordinary skill in the art would recognize from context that Wetzel’s disclosure of “n-functional diamines” and “n-functional dicarboxylic acids” in [0091] was meant to be a disclosure of polyamines and polycarboxylic acids.] Wetzel names useful polyamines which would result in all sp2 bonds through the backbone chains of the 2D polymer, including melamine [0092], and names useful carboxylic acids that would result in all sp2 bonds through the backbone chains of the 2D polymer, including trimesic acid [0093].
Considering the disclosures of Wetzel and Rosado regarding 2D polymers, one having ordinary skill in the art would have had a reasonable expectation of success in forming a 2D polymer from 1,3,5-benzenetricarbonyl trichloride and melamine (because these are both monomers which are taught by Wetzel as forming sp2 bonds through the backbone of a 2D polymer), and, when forming a polyamide from 1,3,5-benzenetricarbonyl trichloride and melamine having a structure according to Zulfiqar’s PA-1, the person having ordinary skill in the art would have been motivated to form a material which has intermolecular hydrogen bonding between layers (as taught by Rosado and Wetzel) in order to increase strength and stiffness of the material. It would have been obvious to the person having ordinary skill in the art, therefore, to have formed a polymeric material by reacting 1,3,5-benzenetricarbonyl trichloride and melamine, as taught by Zulfiqar and shown in scheme 1, by forming the polymer as a two-dimensional material which has intermolecular hydrogen bonds (i.e., hydrogen bonds in a third dimension), as taught by Rosado and Wetzel, in order to provide a material having improved mechanical properties such as strength and stiffness.
As to claims 29 and 30, modified Zulfiqar fails to teach utilizing a combination of solvents as recited in claims 29 and 30.
Claims 29 and 30 are product-by-process claims. Case law has established that the patentability of a product-by-process is determined by the patentability of the product itself, i.e., that the patentability of a product does not depend upon its method of production (MPEP 2113). The process limitations are only given consideration regarding patentability if there is criticality to the structure implied by the steps of the process. Because the claims as presently drafted do not contain any limitations which materially distinguish the presently claimed material suggested by modified Zulfiqar, it is evident that the material which is presently claimed is met by the material suggested by modified Zulfiqar, notwithstanding any difference in the method by which the material of modified Zulfiqar is made.
As to claims 31 and 32, modified Zulfiqar fails to teach a TGA weight loss of no more than 5% at 312 C. However, given that modified Zulfiqar suggests a polymer which has the same structure as the polymer YZ-2 shown in instant figure 26B, there is reasonable basis to conclude that when analyzed using the same sample preparation and under the same TGA conditions, the material of modified Zulfiqar would exhibit substantially the same weight loss properties as instant YZ-2 shown in instant figure 26C (i.e., a TGA weight loss of 5% at 312 C).
Claim(s) 17, 19-25 and 29-32 is/are rejected under 35 U.S.C. 103 as being unpatentable over Rosado et al (High strength films from oriented, hydrogen-bonded “graphamid” 2D polymer molecular ensembles. Sci Rep 8, 3708 (2018)) in view of Wetzel et al (US 2017/0240706).
As to claims 17, 19-25, 31 and 32, Rosado discloses that two dimensional materials such as graphene have extraordinary stiffness and strength, but also low fracture toughness because they are brittle. Rosado discloses a 2D polymer, graphamid, which is analogous to linear PPTA (poly(p-phenylene terephthalamide). See p 1. Graphamid consists of C6 aromatic rings interconnected in six directions by amide bridges to form a 2D covalent polymer (p 2, last two paragraphs). The 2D nature of graphamid gives it strength and stiffness in all in-plane directions, unlike in linear PPTA (p 2, first four lines).
The 2D aramid polymer (graphamid) disclosed by Rosado differs from the presently recited 2D aramid polymer recited in claim 17 (and recited more narrowly in claim 25) because the aromatic rings in graphamid are interconnected in six directions by amide bridges, while the aromatic rings in the presently recited 2D aramid polymer are interconnected in three directions by amide bridges.
Like Rosado, Wetzel teaches that graphene is an example of a 2D material, and, teaches that because graphene is a network of very stiff sp2 double bonds, it is highly resistant to fracture initiation, but exhibits brittle behavior [0008].
Wetzel also discloses 2D polymer compounds that have continuous bond networks that extend in all directions in the material plane, so that they can demonstrate high stiffness and strength in all directions [0029]. Wetzel teaches producing the 2D polymers using a step-growth approach, wherein at least one monomer must have 3 or more functional groups. The greater the functionality of each molecule, the greater the crosslink density and smaller the pores of the resulting polymer [0086]. Wetzel teaches that the ability to create a tailored pore size and pore chemistry can result in very high selectivity in selective barriers [0118].
Wetzel teaches that producing graphamid (i.e., the 2D polymer disclosed in Rosado) that is analogous to graphene would require the use of hexaaminobenzene and benzene hexacarboxylic acid. To form similar 2D aromatic polyamides with a lower degree of crosslinking, Wetzel discloses three types of monomer combinations, including (as the third type) a combination of n-functional carboxylic acids/chlorides/esters with n≥3 and n-functional amines with n≥3 [0091]. [One having ordinary skill in the art would recognize from context that Wetzel’s disclosure of “n-functional diamines” and “n-functional dicarboxylic acids” in [0091] was meant to be a disclosure of polyamines and polycarboxylic acids.] Wetzel names useful polyamines which would result in all sp2 bonds through the backbone chains of the 2D polymer, including melamine [0092], and names useful carboxylic acids that would result in all sp2 bonds through the backbone chains of the 2D polymer, including trimesic acid [0093].
Considering the disclosures of Rosado and Wetzel, the person having ordinary skill in the art would have been motivated to prepare a 2D aramid polymer having continuous bond networks extending in all directions in the material plane in order to achieve higher stiffness and strength in all directions, compared to analogous linear aramid polymers (see Wetzel [0029]; see Rosado p 2, first four lines). Considering Wetzel’s disclosure in [0091], the person having ordinary skill in the art would have been motivated to form 2D polymers similar to Rosado’s graphamid, but with fewer than six amide linkages interconnecting the aromatic rings, in order to tailor the degree of crosslinking and polymer pore size for an intended application. It would have been obvious to the person having ordinary skill in the art, therefore, to have formed a 2D amide polymer similar to Rosado’s graphamid by replacing the hexafunctional polyamine and polycarboxylic reactants with any of the useful n≥3 polyamine and polycarboxylic reactants named by Wetzel, including melamine and trimesic acid, thereby arriving at a 2D polymer having a structure as recited in claims 17 and 25.
As to the recited hydrogen bonds in a third dimension, Rosado teaches that graphamid stacks with inter-layer hydrogen bonds between molecular sheets, and that the inter-layer hydrogen bonds are responsible for superior shear behavior of graphamid, relative to graphene or graphylene (p 3). Rosado teaches that the tight packing of the graphamid structure forces amide groups to rotate out of plane, which results in a high density of accessible intermolecular hydrogen bonds (p 8). Wetzel similarly teaches that the 2D polymers are able to be stacked into ordered ensembles (abstract), and that the 2D polymer composition may exhibit inter-molecular hydrogen bonding [0029] (i.e., are capable of inter-molecular hydrogen bonding to other similar 2D polymer molecules, see claim 12 of Wetzel). Therefore, it would have been obvious to one of ordinary skill in the art to have formed a 2D amide polymer via reaction of melamine and trimesic monomers, as suggested by Rosado in view of Wetzel, having at least some inter-molecular hydrogen bonding (i.e., hydrogen bonding in a third dimension) in order to improve the shear behavior of the material.
Modified Rosado fails to teach the presently recited FTIR stretching frequencies or TGA weight loss. However, given that modified Rosado suggests a polymer which has the same structure as the polymer YZ-2 shown in instant figure 26B, there is reasonable basis to conclude that when analyzed using the same sample preparation and under the same FTIR or TGA conditions, the material of modified Rosado would exhibit substantially the same FTIR and weight loss properties as instant YZ-2 shown in instant figures 26D and 26C (i.e., stretching at a frequency of about 3213 cm-1 and about 1601 cm-1, and a TGA weight loss of 5% at 312 C).
As to claims 29 and 30, modified Rosado fails to teach utilizing a combination of solvents as recited in claims 29 and 30. Claims 29 and 30 are product-by-process claims. Case law has established that the patentability of a product-by-process is determined by the patentability of the product itself, i.e., that the patentability of a product does not depend upon its method of production (MPEP 2113). The process limitations are only given consideration regarding patentability if there is criticality to the structure implied by the steps of the process. Because the claims as presently drafted do not contain any limitations which materially distinguish the presently claimed material suggested by modified Rosado, it is evident that the material which is presently claimed is met by the material suggested by modified Rosado, notwithstanding any difference in the method by which the material of modified Rosado may be made.
Response to Arguments
Applicant's arguments filed 9/22/2025 have been fully considered.
Applicant argues (p 11) that the cited prior art does not use Lewis acid additives, and therefore, there is no reason to believe that the materials have out-of-plane amides. However, Applicant has not provided any evidence that, without use of Lewis acid additives, out-of-plane structure is completely absent from the formed polyamides. The section of the specification cited by Applicant (which appears to allege only that Lewis acid additives aid in solubility) does not provide any data or evidence which implies that, without Lewis acid additives, such structure will not form.
Applicant further argues (p 12) that Zulfiqar’s TGA thermograms show 40-50% weight loss at 312 C, and that despite Zulfiqar’s teaching that solvent loss contributes to the observed mass loss, one would appreciate that the TGA curves demonstrate that the 2D material of the present disclosure is more thermally stable than Zulfiqar’s polyamides. However, Applicant has not explained how, in view of Zulfiqar’s teaching that solvent loss contributes to the observed mass loss, Zulfiqar’s TGA thermogram can be used to meaningfully compare the thermal stability of Zulfiqar’s material to the instant material.
Applicant further argues (pp 13-14) that the graphamid of Rosado differs from the presently claimed material due to the fact that the aromatic rings in graphamid are interconnected in six directions. However, this argument is unpersuasive for at least the reason that the rejection (which modifies Rosado based on teachings in Wetzel) does not assert that Rosado’s graphamid meets the presently claimed material.
Applicant argues (p 14) that Wetzel does not teach that trifunctional monomers can result in amides which are rotated out-of-plane. However, as set forth in the rejections of record, Wetzel teaches that the 2D polymers are able to be stacked into ordered ensembles (abstract), and that the 2D polymer composition may exhibit inter-molecular hydrogen bonding [0029] (i.e., are capable of inter-molecular hydrogen bonding to other similar 2D polymer molecules, see claim 12 of Wetzel). At least based on this teaching, there is reasonable basis to conclude that Wetzel teaches a material (like Rosado) which has at least some hydrogen bonding in a third dimension (i.e., intermolecular bonding, which must be between planes of two dimensional polymers stacked into ordered ensembles).
Conclusion
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/RACHEL KAHN/ Primary Examiner, Art Unit 1766