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 .
Response to Arguments
Applicant’s arguments, filed 4 May 2026, with respect to the rejection(s) of claim(s) 1-5, 10, and 24 as unpatentable over Weber et al. (Weber, M., & Heckmann, W. (1998), Polymer Bulletin, 40(2), 227-234) in view of Periyasamy et al. (Periyasamy, Thirukumaran, et al., New Journal of Chemistry 40.11 (2016): 9313-9319) under 35 USC §103 have been fully considered and are persuasive. Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of and Iojoiu et al. (Iojoiu Cristina, and Jean-Yves Sanchez. High Performance Polymers 21.5 (2009): 673-692) and Periyasamy et al..
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.
Claim(s) 1-5, 10, and 24 are rejected under 35 U.S.C. 103 as being unpatentable over Iojoiu et al. (Iojoiu Cristina, and Jean-Yves Sanchez. High Performance Polymers 21.5 (2009): 673-692) in view of Periyasamy et al. (Periyasamy, Thirukumaran, et al., New Journal of Chemistry 40.11 (2016): 9313-9319).
As to Claims 1-2, Iojoiu et al. discloses a polysulfone comprising in polymerized form:
(i) A polymerizable bisphenol A (BPA)-based monomer and
(ii) at least one polymerizable 4,4'-dihalophenyl sulfone as a comonomer (see e.g. the polysulfone Udel, which comprises a BPA-based monomer and a polymerizable 4,4'-dihalophenyl sulfone as a comonomer as shown in Sheme 1, pg. 676. See also Illustration 1 below).
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Illustration 1, Representation of the polysulfone Udel, with BPA and 4,4'-dihalophenyl sulfone comonomers indicated.
Iojoiu et al.’s polysulfone is not a bio-based polysulfone and does not comprise (i) at least one polymerizable lignin-based monomer having a structure corresponding to formula (I):
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Illustration 2, reproduction of the lignin-based monomer of Claim 1.
wherein each R' is independently either an H or a methyl group, wherein R2, R3, and R4 are each individually selected from an H or a methoxy group.
Periyasamy et al., also working in the field of polymers, teaches that bisguaiacol F (BGF) is viable green alternative to BPA as a monomer for polymer materials due to the fact that BGF has a similar structure to BPA but is incapable of interfering with hormones (See e.g. abstract and pg. 9313, col. 1, paras 1-2 to col. 2, para 1). Periyasamy et al. further teaches that BGF retains the desirable thermal and mechanical properties of BGA (see e.g. pg. 9313, col. 2, para 1). The BGF monomer taught by Periyasamy et al. has the following formula (see e.g. pg. 9314, Scheme 1):
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Illustration 3, reproduction of the lignin-based BGF monomer of Periyasamy et al. (top) and the bio-based polysulfone that results from replacing Iojoiu et al.’s BPA monomer with the BGF monomer taught by Periyasamy et al. (bottom).
Which reads on the polymerizable lignin-based monomer of claim 1 when R1, R2, and R3 are H and R4 is a methoxy group.
It would therefore have been obvious to one of ordinary skill in the art prior to the filing date of the claimed invention to replace the BPA monomer of Iojoiu et al.’s polysulfone with the lignin-based monomer BGF monomer taught by Periyasamy et al. to yield a bio-based polysulfone that reads on the instantly-claimed polysulfone. Said artisan would have been motivated to make such a substitution because Periyasamy et al. teaches that BGF is a green material and does not interfere with hormones.
As to Claim 3, Iojoiu et al. in view of Periyasamy et al. discloses the bio-based polysulfone of claim 1, wherein the bio-based polysulfone is represented by the formula:(II)
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Illustration 4, reproduction of the bio-based sulfone of Claim 3 .
(see e.g., Scheme 1 of Iojoiu et al. and Illustrations 1-3 above. Note that replacing the BPA monomer with a BGF monomer as proposed in the rejection of Claim 1 yields a bio-based polysulfone that reads on the claimed polysulfone)
wherein n [degree of polymerization] =2-2000, wherein each R' is independently either an H or a methyl group, and wherein R2, R3, and R4 are each individually selected from an H or a methoxy group (i.e., Iojoiu et al.’s polymer has an average polymer chain molecular weight (Mn) of ~30,000 g/mol, as per pg. 675, para 3 of Iojoiu et al.. The degree of polymerization (n) is defined as the average polymer chain molecular weight (Mn) divided by the molecular weight of the unit monomer (Mo). In this case, n = Mn/Mo = 30,000/442 = 67.87, which lies within the claimed range of 2-2,000 and thereby anticipates the instantly-claimed range).
As to Claim 4, Iojoiu et al. in view of Periyasamy et al. discloses the bio-based polysulfone of Claim 1, wherein the polymerizable lignin-based monomer comprises p,p'-bisguaiacol F (see e.g. Illustration 3 above, in which the BGF monomer is in a para-para orientation).
However, Iojoiu et al. in view of Periyasamy et al. does not disclose a mixture of p,p'-bisguaiacol F, m,p'-bisguaiacol F, and o,p'-bisguaiacol F and wherein the resulting bio-based polysulfone is represented by the following structure:
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Illustration 5, reproduction with annotation of the bio-based sulfone of Claim 4..
wherein x+y+z=1, 0<x<1, 0<y<1, and 0<z<1; and wherein x, y, and z represent the molar fractions of the respective chemical units.
However, absent any evidence of the criticality of the orientation of the attachment of the BGF monomer to the sulfone (i.e., whether the monomer is p,p’, m,p’, or o,p’ BGF), one of ordinary skill in the art would have reasonably expected that the m,p’-BGF and o,p’-BGF isomers would have similar chemical and physical properties to p,p’-BGF (see MPEP §2144.09, Close Structural Similarity Between Chemical Compounds [Homologs, Analogues, Isomers]).
As such, one of ordinary skill in the art prior to the filing date of the claimed invention would have found it obvious to substitute some amount of the p,p’-BGF monomers in the polymer taught by the combined teachings of Iojoiu et al. and Periyasamy et al. with m,p’-BGF and o,p’-BGF isomers to arrive at the instantly-claimed polymer and the instantly-claimed mole fractions. Such a substitution would yield no new benefit that would not have been reasonably expected by said artisan given the homologous nature of these three isomers.
As to Claim 5, Iojoiu et al. in view of Periyasamy et al. discloses the bio-based polysulfone of Claim 1, wherein the polymerizable lignin-based monomer comprises p,p'-bisguaiacol F (see e.g. Illustration 3 above, in which the BGF monomer is in a para-para orientation).
However, Iojoiu et al. in view of Periyasamy et al. does not disclose a mixture comprising p,p'-bisguaiacol A, m,p'- bisguaiacol A, and o,p'-bisguaiacol A, and wherein the resulting bio-based polysulfone is represented by the following structure:
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Illustration 6, reproduction with annotation of the bio-based sulfone of Claim 5.
wherein x+y+z=1, 0<x<1, 0<y<1, and 0<z<1; and whereinx, y, and z represent the molar fractions of the respective chemical units.
However, given the close structural similarity between p,p'-bisguaiacol A (p,p'-BGA) and p,p'-bisguaiacol F (p,p'-BGF) as shown below, and absent any evidence that the presence of two additional methyl groups substantially alter the properties of the p,p'-BGF monomer, one of ordinary skill in the art prior to the filing date of the invention would have expected p,p'-BGF and p,p'-BGA to be analogous monomers with similar physical and chemical properties (see MPEP §2144.09, Close Structural Similarity Between Chemical Compounds [Homologs, Analogues, Isomers]).
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Illustration 7, comparison of p,p'-bisguaiacol F and p,p'-bisguaiacol A monomers.
Further regarding claim 5, Iojoiu et al. in view of Periyasamy et al. as applied above discloses a bio-based polysulfone comprising p,p'-bisguaiacol A, but does not disclose a mixture comprising p,p'-bisguaiacol A, m,p'- bisguaiacol A, and o,p'-bisguaiacol A.
However, absent any evidence of the criticality of the orientation of the attachment of the BGA monomer to the sulfone (i.e., whether the monomer is p,p’, m,p’, or o,p’ BGA), one of ordinary skill in the art would have reasonably expected that the m,p’-BGA and o,p’-BGA isomers would have similar chemical and physical properties to p,p’-BGA (see MPEP § 2144.09, Close Structural Similarity Between Chemical Compounds [Homologs, Analogues, Isomers]).
As such, one of ordinary skill in the art prior to the filing date of the claimed invention would have found it obvious to substitute some amount of the p,p’-BGA monomers in the polymer taught by the combined teachings of Iojoiu et al. and Periyasamy et al. as applied above with m,p’-BGA and o,p’-BGA isomers to arrive at the instantly-claimed polymer and the instantly-claimed mole fractions. Such a substitution would yield no new benefit that would not have been reasonably expected by said artisan given the homologous nature of these three isomers.
As to Claim 10, Iojoiu et al. in view of Periyasamy et al. teaches the bio-based polysulfone of claim 1, but is silent as to whether the bio- based polysulfone has a zwitterionic functionality, and the zwitterionic functionality is selected from dimethylammonioacetate (carboxybetaine) groups, dimethylammoniopropyl sulfonate (sulfobetaine) groups, or combinations thereof.
However, it has been held that if the prior art teaches a chemical structure that is identical to the claimed chemical structure, the properties applicant discloses and/or claims are necessarily present in the prior art structure (see MPEP § 2112.01, “Composition, Product, and Apparatus Claims [R-10.2019]”). In the instant case, the polysulfone taught by Iojoiu et al. and Periyasamy et al. as set forth meets all of the structural limitations of the instantly-claimed polysulfone, as set forth in the rejection of claim 1 above. One of ordinary skill in the art would therefore have reasonably expected the polysulfone taught by Iojoiu et al. and Periyasamy et al. to also be zwitterionic and to possesses a zwitterionic functionality is selected from dimethylammonioacetate (carboxybetaine) groups, dimethylammoniopropyl sulfonate (sulfobetaine) groups.
As to Claim 24, Iojoiu et al. in view of Periyasamy et al. discloses the bio-based polysulfone of Claim 1, wherein the bio- based polysulfone has a structure presented in Claim 1 (see e.g., Scheme 1 of Iojoiu et al. and Illustrations 1-3 above. Note that replacing the BPA monomer with a BGF monomer as proposed in the rejection of Claim 1 yields a bio-based polysulfone that reads on the claimed polysulfone)
wherein n [degree of polymerization] =2-2000, wherein each R' is independently either an H or a methyl group, and wherein R2, R3, and R4 are each individually selected from an H or a methoxy group (i.e., Iojoiu et al.’s polymer has an average polymer chain molecular weight (Mn) of 30,000 g/mol, as per pg. 675, para 3 of Iojoiu et al.. The degree of polymerization (n) is defined as the average polymer chain molecular weight (Mn) divided by the molecular weight of the unit monomer (Mo). In this case, n = Mn/Mo = 30,000/442 = 67.8, which lies within the claimed range of 2-2,000 and thereby anticipates the instantly-claimed range).
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Illustration 8: proposed modification of Iojoiu et al. with Periyasamy et al., which reads on claim 3 when R1, R2, and R3 are H and R4 is a methoxy group.
Iojoiu et al. in view of Periyasamy et al. as applied above does not disclose a polysulfone wherein a functionality described as O-R5 directly bonded to a phenyl ring, and wherein R5 is individually selected from an H, a COOH, an SO3H, or an CH2CH2CH2NH2 and subsequent quarternary ammonium and betaine-type zwitterions.
The structure presented in Illustration 8 above differs from the instantly-claimed polysulfone in that the above structure has a methyl group (CH3) at the position where the R5 group of the claimed polysulfone is present. The instant claim limits the R5 group to be selected from an H, COOH, SO3H, CH2CH2CH2NH2 quaternary ammonium, and betaine-type zwitterions, which does not contain CH3.
However, the instant claim recites “wherein R1 is either an H or a methyl group,” which implies that an H group and a CH3 group are functionally equivalent chemical groups with respect to a polysulfone. It would therefore have been obvious to one of ordinary skill in the art prior to the filing date of the instantly-claimed invention to substitute the CH3 group of the polysulfone taught by the combined teachings of Iojoiu et al. and Periyasamy et al. with an H group, which reads on the instantly-claimed polysulfone, becuase the substitution of an H group for a CH3 group would represent the use of an equivalent chemical functional group that would fail to alter the properties of the prior art structure in a patentably distinct manner.
Claim(s) 7-9 are rejected under 35 U.S.C. 103 as being unpatentable over Iojoiu et al. (Iojoiu Cristina, and Jean-Yves Sanchez. High Performance Polymers 21.5 (2009): 673-692) in view of Periyasamy et al. (Periyasamy, Thirukumaran, et al., New Journal of Chemistry 40.11 (2016): 9313-9319) as applied to claim 1 above, and further in view of Lee et al. (Lee, Sun Hwa, et al., RSC Advances 7.45 (2017): 28358-28365).
As to Claim 7, Iojoiu et al. in view of Periyasamy et al. teaches the bio-based polysulfone of claim 1.
However, Iojoiu et al. in view of Periyasamy et al. does not teach a bio-based polysulfone that comprises at least one additional comonomer selected from the group consisting of 2,2'-diallylbisphenol A, bisphenol A, bisphenol F, bisphenol S, 2,2'-biphenol, 4,4'-biphenol, multiphenol and hydroquinone.
Lee et al., also working in the field of sulfone polymers, teaches that adding a 2,2’-diallylbisphenol A monomer to a sulfone polymer yields a composite polymer having remarkable dimensional stability and barrier properties (see e.g. the sulfonated poly(arylene sulfone) that is prepared with a 2,2’-diallylbisphenol A monomer. Abstract, pg. 28358, col. 2, paras 1-2, pg. 29359, col. 1, para 1, , and Fig. 2).
It would therefore have been obvious to one of ordinary skill in the art prior to the filing date of the claimed invention to modify the bio-based polysulfone of Iojoiu et al. in view of Periyasamy et al. by adding the 2,2’-diallylbisphenol A monomer taught by Lee et al. to the copolymer, because Lee teaches that the addition of this monomer to a sulfone polymer yields a composite polymer having remarkable dimensional stability and barrier properties.
As to Claim 8, Iojoiu et al. in view of Periyasamy et al. and Lee et al. teaches the bio-based polysulfone of claim 7.
As shown below, the polysulfone of the combined teachings of Iojoiu et al., Periyasamy et al. and Lee et al. as set forth in the rejection of claim 7 above would read on the structure presented in claim 8.
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Illustration 8, the bio-based polysulfone that results from the combined teachings of Iojoiu et al., Periyasamy et al. and Lee et al. as set forth in the rejection of claim 7 above.
Additionally, the polysulfone described above, having svome amount of 2,2'-diallylbisphenol A, would satisfy the claimed molar fractions of x+y=1 where 0<x≤1.
As to Claim 9, Iojoiu et al. in view of Periyasamy et al. teaches the bio-based polysulfone of claim 1.
However, Iojoiu et al. in view of Periyasamy et al. does not teach a bio-based polysulfone that is modified with one or more functional groups selected from sulfonates, carboxylates, ammoniums, amines, alcohols, sulfobetaines, carboxybetaines, 2,2'- diallylbisphenol A, and poly(ethylene glycol) (PEG).
Lee et al., also working in the field of sulfone polymers, teaches that adding a 2,2’-diallylbisphenol A monomer to a sulfone polymer yields a composite polymer having remarkable dimensional stability and barrier properties (see e.g. the sulfonated poly(arylene sulfone) that is prepared with a 2,2’-diallylbisphenol A monomer. Abstract, pg. 28358, col. 2, paras 1-2, pg. 29359, col. 1, para 1, , and Fig. 2).
It would therefore have been obvious to one of ordinary skill in the art prior to the filing date of the claimed invention to modify the bio-based polysulfone of Iojoiu et al. in view of Periyasamy et al. by adding the 2,2’-diallylbisphenol A monomer taught by Lee et al. to the copolymer, because Lee teaches that the addition of this monomer to a sulfone polymer yields a composite polymer having remarkable dimensional stability and barrier properties.
Conclusion
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/A.M.H./Examiner, Art Unit 1723
/CHRISTIAN ROLDAN/Primary Examiner, Art Unit 1723
05/20/2026
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