Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on February 17, 2026 has been entered.
Response to Amendment
The Amendment filed February 17, 2026 has been entered. Examiner acknowledges the addition of new claims 18-31. Claims 1-5 and 18-31 remain pending in the application.
Response to Arguments
Applicant's arguments filed February 17, 2026 have been fully considered but they are not persuasive. The rejection of claims 1-5 under U.S.C. §103 is maintained.
Applicant argues that Yamaguchi provides no motivation to perform the claimed method of increasing decarboxylation during polymerization so that the resulting copolymer molecule has an average frequency of non-carboxylated monomeric repeating units of at least 5 molar percent. This argument is not persuasive. Yamaguchi expressly teaches that carbon dioxide evolves during polymerization as a result of decarbonization of maleic acid and/or the acid-type maleic acid polymer, that the amount of carbon dioxide evolved is proportional to the amount of hydrogen peroxide added, and that the amount of decarbonization and resulting carboxyl-group content of the polymer may thereby be controlled as required. Thus Yamaguchi directly teaches adjusting a polymerization parameter to control the degree of decarboxylation occurring during polymerization. Selection of reaction conditions producing at least 5 molar percent non-carboxylated repeating units would have been an obvious optimization of the controllable decarboxylation process taught by Yamaguchi.
Applicant further argues that increasing peroxide or otherwise modifying Yamaguchi would produce discoloration and render the resulting product unsatisfactory for its intended purpose. This argument is not persuasive because the rejection does not require indiscriminately maximizing oxidative severity or operating outside of Yamaguchi’s disclosed process conditions. Rather, Yamaguchi itself teaches controlling peroxide addition to control decarboxylation and polymer carboxyl-group content. Further, claims 1 does not require any particular product color, and Applicant has not established that carrying out Yamaguchi’s disclosed process so as to obtain the claimed minimum decarboxylation level necessarily produces a polymer unsuitable for water-treatment or detergent applications.
The Third Farrar Declaration has also been considered but is not sufficient to overcome the rejection. The Declaration characterizes its first-round testing as reproductions of Yamaguchi Examples 8 and 9, but the reported procedure uses ferrous ammonium sulphate (FAS), i.e., an Fe2+ catalyst. Because the Declaration changes the metal-ion oxidation state used in the relied-upon Yamaguchi examples, its testing does not establish the result of performing Yamaguchi’s disclosed examples as taught. This distinction is material because Yamaguchi identifies the metal-ion and peroxide conditions as relevant polymerization parameters.
The later testing likewise does not cure this deficiency because the second and third round experiments continue to employ FAS rather than the Fe3+ catalyst used in Yamaguchi’s Examples 8 and 9. Consequently, the Declaration’s reported decarboxylation and discoloration results do not demonstrate that Yamaguchi’s disclosed process, as actually taught, would fail to produce or render obvious the claimed average frequency of at least 5 molar percent non-carboxylated monomeric repeating units.
Moreover, even under the altered experimental conditions selected by Declarant, the third-round testing produced reported decarboxylation values of 4.94% and 4.74%. These values are very near the claimed 5 molar percent boundary and do not establish that the claimed threshold is critical, produces unexpected results, or could not have been reaches by routine adjustment of the process variables Yamaguchi expressly identifies as controlling decarboxylation. Rather, these results are consistent with Yamaguchi’s teaching that decarboxylation is a controllable process variable.
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 26 and 29-31 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 26 recites that the copolymer molecule is characterized by “intramolecular electrostatic repulsion between adjacent carboxylic acid repeating units along a polymer backbone”, wherein the adjacent carboxylic acid repeating units are present in combination with non-carboxylated monomeric repeating units derived from increasing decarboxylation. The specification discloses that the presence and proximity of di-carboxylic acid groups along the copolymer backbone provides electrostatic repulsion, rigidity, and stability, and separately discloses that increasing decarboxylation can produce non-carboxylated monomeric repeating units. However, the specification does not disclose adjacent carboxylic acid repeating units or expressly describe intramolecular electrostatic repulsion between such adjacent repeating units in combination with the decarboxylation-derived non-carboxylated repeating units now recited.
Claim 29 recites that the copolymer molecule includes di-carboxylic acid functional groups positioned along the polymer backbone at “spacings effective to generate intramolecular electrostatic repulsion between adjacent carboxylic acid groups”, thereby imparting backbone rigidity that resists coiling or collapse in an aqueous medium. The specification discloses generally that the presence and proximity of di-carboxylic acid groups along the copolymer backbone provides electrostatic repulsion, rigidity, and reduced coiling or collapse in harsh water conditions. However, the specification does not disclose di-carboxylic acid functional groups positioned at particular spacings effective to generate repulsion between adjacent carboxylic acid groups. The claim therefore introduces a specific spatial and relational arrangement not expressly conveyed by the original disclosure.
Claim 30 recites that treatment of an aqueous system with the copolymer molecule produces greater degree of calcite crystal-habit modification than treatment with a “polymaleic acid homopolymer produced with reduced decarboxylation.” The specification discloses comparative testing of an enhanced copolymer and PMA and states that the enhanced copolymer exhibited improved calcite crystal-habit modification relative to PMA. However, the specification does not identify the PMA material used in the comparative testing as a polymaleic acid homopolymer produced with reduced decarboxylation. The disclosure of increasing decarboxylation in forming the enhanced copolymer does not establish that the tested PMA comparator was produced by a reduced-decarboxylation process. Claim 31 is rejected due to its dependency upon claim 30.
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.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 23 and 29-31 rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Regarding claim 23, recitation of polymer molecules having an “average molecular weight” between 300 and 3,000 Daltons. The does not identify whether “average molecular weight” refers to number-average molecular weight (Mn), weight-average molecular weight (Mw), or another recognized polymer molecular-weight measure. Because these values may differ for the same polymer, the scope of claim 23 is unclear.
Regarding claim 29, recitation of di-carboxylic acid functional groups positioned at “spacings effective” to generate intramolecular electrostatic repulsion and impart backbone rigidity that “resists coiling or collapse” in an aqueous medium. The claim does not define the required spacing, the degree of resistance to coiling or collapse, or the aqueous conditions under which the limitation is evaluated. Accordingly, the scope of claim 29 is unclear.
Regarding claim 30, recitation that treatment with the copolymer produces “a greater degree of calcite crystal habit modification than treatment with a polymaleic acid homopolymer produced with reduced decarboxylation” however, the claim does not define the treatment conditions, the method for measuring the degree of crystal habit modification, or what constitutes “reduced decarboxylation” in the comparator polymer. Accordingly, one of ordinary skill in the art cannot determine with reasonable certainty when the comparative limitation is satisfied.
Regarding claim 31, in addition to being rejected due to its dependency upon claim 30, claim 31 further recites “crystal distortion of over 50% of potential cubic macro-lattices”, but does not define how crystal distortion is measured or what constitutes a potential cubic macro-lattice. Therefore, claim 31 is indefinite for these combined reasons.
Claim Rejections - 35 USC § 103
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 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.
Claims 1-5, 18, 22-25 and 27-28 are rejected under 35 U.S.C. 103 as being unpatentable over Yamaguchi (US5135677).
Regarding claim 1, Yamaguchi discloses a method of preparing in-situ a substantially maleic acid copolymer, comprising: polymerizing at least a portion of a plurality of maleic acid monomer components (described in Yamaguchi par.2 of col. 4), wherein some of such maleic acid monomer components are transformed into monomeric repeating units within each of a plurality of polymer molecules, increasing decarboxylation during said polymerizing (Yamaguchi col. 7 lines 30-40 where decarbonization is a reaction with hydrogen peroxide that removes a carboxyl group and releases carbon dioxide), forming in-situ (Yamaguchi col. 9 line 13-14) a copolymer molecule comprising at least one decarboxylated portion of said copolymer molecule (Yamaguchi col. 7 lines 38-48 describe that the amount of carbon dioxide evolved and thereby the non-carboxylated units are formed directly proportional to the amount of hydrogen peroxide added forming the copolymer).
Yamaguchi does not disclose increasing an average frequency of non-carboxylated monomeric repeating units in said polymer molecules to at least approximately 5 molar%. However, Yamaguchi does disclose that the molar% of the non-carboxylated monomeric repeating units in said polymer molecules may be increased proportionally with the amount of hydrogen peroxide added in the reaction adding that “hydrogen peroxide should be used in an amount of 8-100 g, preferably 10-80 g, and more preferably 15-50 g; per mol of the monomer component. (Col 7. Lines 38-57) It would have been obvious to one of ordinary skill in the art at the time of filing to adjust the mass of hydrogen peroxide added to increase the molar% to at least 5 as a matter of optimization and according to Yamaguchi, “This is a great advantage of the ·present invention because the acid-type maleic acid polymer can be made suitable for a broad range of applications by controlling the amount of carboxylic acid which greatly affects the physical properties and performance of the acid-type maleic acid polymer.”
Regarding claim 2, Yamaguchi discloses a method of claim 1, wherein said polymerizing comprises aqueously polymerizing. (Col. 9 line 13-14)
Regarding claim 3, Yamaguchi discloses a method of claim 2, wherein said increasing decarboxylation comprises adjusting one or more reaction parameters selected from the group of temperature, metal catalyst concentration, hydrogen peroxide concentration, and other reaction additives. (Col 7. Lines 38-57)
Regarding claim 4, Yamaguchi discloses a method of claim 2, wherein said copolymer molecule further comprises at least one terminal hydroxyl group. (reaction with hydrogen peroxide in the presence of the metal ion chosen from the list at the end of Yamaguchi col 6 and par. 1 of col. 7 and heat will form at least one terminal hydroxyl group.)
Regarding claim 5, Yamaguchi discloses a method of claim 3, wherein said polymerizing further comprises co-polymerizing one or more co-monomers capable of reacting in a free-radical aqueous polymerizing system. (Col. 5 lines 9-12)
Regarding claim 18, Yamaguchi discloses a method of claim 1, wherein said polymerizing is carried out by aqueous (Yamaguchi col. 9 “in an aqueous solution”) free-radical polymerization (Yamaguchi claim 1, col. 4 and abstract, polymerization of Yamaguchi’s unsaturated monomers using hydrogen peroxide in the presence of a metal ion in an aqueous free-radical polymerization process).
Regarding claim 22, Yamaguchi discloses a method of claim 1, wherein said copolymer molecule comprises terminal hydroxyl groups formed during said polymerizing (Yamaguchi col. 5 lines 19-21 isoprenol, prenol, isoprene alcohol and by example of formula 1 each possessing terminal hydroxyl groups).
Regarding claim 23, Yamaguchi discloses a method of claim 1, wherein said polymer molecules have an average molecular weight between 300 Daltons and 3,000 Daltons (construing the recited “average molecular weight” as encompassing number-average molecular weight, Yamaguchi col. 8 teaches “an acid-type maleic acid polymer which has a number-average molecular weight of 300-5000, preferably 400-3000, and a D-value smaller than 2.5, preferably smaller than 2.0”).
Regarding claim 24, Yamaguchi discloses a method of claim 1, wherein maleic acid repeating units are present in said copolymer molecule in an amount greater than 50 molar percent (Yamaguchi col. 4 lines 11-14).
Regarding claim 25, Yamaguchi discloses a method of claim 1, wherein decarboxylated maleic acid repeating units are present in said copolymer molecule (Yamaguchi col. 16 describes the copolymer having acrylic acid structural units in the molecule and further teaches in col. 7 that the polymerization evolves carbon dioxide as a result of decarbonization from the maleic acid and/or acid-type maleic acid polymer present in the polymerization system).
Regarding claim 27, Yamaguchi discloses a method of claim 1, wherein said copolymer molecule comprises mono-carboxylic acid repeating units (Yamaguchi col. 16 “acrylic acid”), non-ionic repeating units (Yamaguchi col. 5 provides examples non-ionic repeating units in embodiments including hydroxyl groups and Formula 2 shows (OC2H4) repeating groups of ethylene oxide), and terminal hydroxyl groups (Yamaguchi col. 5 lines 19-21 isoprenol, prenol, isoprene alcohol and by example of formula 1 each possessing terminal hydroxyl groups).
Regarding claim 28, Yamaguchi discloses a method of preparing in-situ a substantially maleic acid copolymer, comprising: polymerizing at least a portion of a plurality of maleic acid monomer components (Yamaguchi described in par.2 of col. 4), wherein some of such maleic acid monomer components are transformed into monomeric repeating units within each of a plurality of polymer molecules, increasing decarboxylation during said polymerizing (col. 7 lines 30-40 where decarbonization is a reaction with hydrogen peroxide that removes a carboxyl group and releases carbon dioxide), forming in-situ (Yamaguchi col. 9 line 13-14) a copolymer molecule comprising at least one decarboxylated portion of said copolymer molecule (Yamaguchi col. 7 lines 38-48 describe that the amount of carbon dioxide evolved and thereby the non-carboxylated units are formed directly proportional to the amount of hydrogen peroxide added forming the copolymer), wherein said increasing decarboxylation results in the copolymer molecule having an average frequency of non-carboxylated monomeric repeating units of at least 5 molar percent (Yamaguchi col.7 lines 3-42 teaches carbon dioxide evolution during polymerization results from decarbonization of maleic acid and/or the acid-type maleic acid polymer and that the amount of carbon dioxide evolved is proportional to the amount of hydrogen peroxide added and that the amount of decarbonization and correspondingly the carboxyl-group content of the polymer may be controlled as required by controlling hydrogen peroxide addition), wherein said copolymer molecule comprises di-carboxylic acid repeating units distributed along a polymer backbone in combination with decarboxylation-derived non-carboxylated repeating units (Yamaguchi col. 16 polymerizes maleic acid to form the acid-type polymaleic acid backbone and teaches that the resulting polymer contains the acrylic acid structure originating from the decarbonization that took place at the time of polymerization).
Claims 19-21 are rejected under 35 U.S.C. 103 as being unpatentable over Yamaguchi (US5135677) as applied to claim 1 above, and further in view of Shaghaghi (US20080058470A1).
Regarding claim 19, Yamaguchi discloses the method according to claim 1, wherein said increasing decarboxylation produces monomeric repeating units derived from maleic acid monomer components within said copolymer molecule.
Yamaguchi does not expressly disclose the monomeric repeating units are non-ionic.
Shaghaghi is directed to maleic-anhydride based free-radical chemistry and teaches that maleic anhydride reacts with a free-radical generating polymerization catalyst, such as benzoyl peroxide, to form modified maleic anhydride. Shaghaghi par. [0014-0017] further discusses prior maleic anhydride free-radical polymerization studies and teaches that Braun and co-workers reported that free-radical polymerization of maleic anhydride proceeds with carbon dioxide cleavage and produces a polymer consisting mainly of cyclopentanone repeating units. Shaghaghi illustrates the cyclopentanone repeating-unit structure in Fig. 2. The cyclopentanone repeating units taught by Shaghaghi are decarboxylation-derived, non-carboxylated repeating units and are non-ionic because they do not contain ionizable carboxylic-acid functionality.
It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to carry out Yamaguchi’s disclosed maleic-acid aqueous polymerization process under decarboxylation-increasing conditions, as expressly taught by Yamaguchi, with the understanding from Shaghaghi that free-radical maleic-derived polymerization with carbon dioxide cleavage was known to produce decarboxylation-derived, non-carboxylated, non-ionic repeating units. Yamaguchi provides the motivation to control and increase decarboxylation during polymerization by adjusting hydrogen peroxide in order to control the carboxyl-group content and properties of the resulting water-treatment polymer. Shaghaghi provides the additional art-recognized teaching that maleic-derived free-radical polymerization with carbon dioxide cleavage can produce non-carboxylated cyclopentanone repeating units. Accordingly, the recited production of non-ionic monomeric repeating units derived from maleic acid monomer components would have been an obvious result of applying known maleic-derived decarboxylation chemistry to the controllable decarboxylation process taught by Yamaguchi.
Regarding claim 20, Yamaguchi discloses the method according to claim 1, wherein said increasing decarboxylation produces non-ionic monomeric repeating units (Shaghaghi par. [0014-0017] “cyclopentanone”) within said copolymer molecule.
Regarding claim 21, Yamaguchi discloses the method according to claim 1, wherein said copolymer molecule comprises both dicarboxylic acid repeating units (Yamaguchi Abstract, col. 2 and throughout “an acid-type polymaleic acid and acid-type maleic acid copolymer”, maleic acid derived repeating units contain two carboxylic acid groups per repeating unit) and decarboxylation-derived non-carboxylated repeating units along a polymer backbone (Shaghaghi par. [0014-0017] “cyclopentanone”).
Conclusion
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/W.A.G./ Examiner, Art Unit 1779
/Bobby Ramdhanie/ Supervisory Patent Examiner, Art Unit 1779
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