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 .
Claim Rejections - 35 USC § 102
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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claim(s) 1-5 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Osuji (WO 2022/032236).
With respect to claim 1, the claim requires “A positively charged quaternary ammonium salt polymer catalyst, which is prepared from a positively charged quaternary ammonium salt precursor by polymerization and anion exchange,” Osuji teaches a positively charged quaternary-ammonium salt polymer prepared from a positively charged quaternary-ammonium salt precursor by polymerization and anion exchange (Osuji 9, line 14-17) (Osuji 49, line 16-26) (Osuji 50, line 3-12). claim 1 further requires “the positively charged quaternary ammonium salt precursor is a reaction product of an acrylate and a haloalkane; wherein the acrylate is selected from the group consisting of dimethylaminoethyl acrylate, dimethylaminoethyl methacrylate, ethyl 3-(dimethylamino)acrylate and a mixture thereof; and the haloalkane is selected from the group consisting of bromoundecane, bromododecane, bromotetradecane, bromohexadecane, bromoeicosane, chlorododecane, chlorotetradecane, chlorohexadecane, and a mixture thereof.” Osuji teaches synthesizing 2-(methacryloyloxy)ethyl tetradecyl dimethyl ammonium bromide (METDAB) by reacting 2-(dimethylamino)ethyl methacrylate with 1-bromotetradecane in acetone (Osuji 49, line 16-26) (Osuji 50, line 3-12).
Regarding claim 2, Osuji teaches that the acrylate is 2-(dimethylamino)ethyl methacrylate and the haloalkane is 1-bromotetradecane (Osuji 49, line 16-22).
Regarding claim 3, Osuji teaches reacting 2-(dimethylamino) ethyl methacrylate with 1-bromotetradecane in acetone to obtain the positively charged quaternary-ammonium salt precursor METDAB; b) polymerizing and crosslinking the METDAB precursor under ultraviolet irradiation to obtain a polymer; and c) after polymerization, immersing the polymer in an aqueous KI solution to exchange bromide anions in the polymer with iodide anions (Osuji 9, line 16-22). (Osuji 49, line 16-26) (Osuji 50, line 3-12) .
Regarding claim 4, Osuji teaches performing the reaction between 2-(dimethylamino)ethyl methacrylate and 1-bromotetradecane at 45°C for 48 hours. The disclosed temperature of 45°C is within the claimed range of 10–200°C, and the disclosed reaction time of 48 hours is within, and at the endpoint of, the claimed range of 1–48 hours (Osuji 49, line 18-22).
Regarding claim 5, Osuji teaches mixing the positively charged quaternary-ammonium salt precursor METDAB with water, the photoinitiator 2-methoxy-2-phenylacetophenone, and the crosslinking agents OEG-DMA and EG-DMA, followed by crosslinking/polymerization under ultraviolet irradiation to obtain the polymer. Thus, Osuji teaches alternative b1) of claim 5.
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) 6 is/are rejected under 35 U.S.C. 103 as being unpatentable over Osuji (WO 2022/032236).
Osuji does not explicitly teach an initiator-to-crosslinking-agent mass ratio of 1:(0.5–2) or an ultraviolet crosslinking time of 0.5–5 minutes. However, Osuji teaches that the amounts of photoinitiator and crosslinking agent may be varied over broad ranges, including approximately 0.01–6 wt% photoinitiator and approximately 0.1–12 wt% crosslinking agent (Osuji 50, line 3-12). Osuji further teaches that the photoinitiator level may be critical and investigates the effects of photoinitiator loading on the crosslinking and preservation of the polymer morphology (Osuji 50, line 3-12).
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to select the relative amounts of photoinitiator and crosslinking agent from the workable ranges taught by Osuji and to adjust the duration of UV irradiation to provide sufficient polymerization and crosslinking while reducing unnecessary irradiation and processing time. The amounts of photoinitiator and crosslinking agent and the duration of ultraviolet irradiation are process variables affecting the rate and extent of photopolymerization. Selection of an initiator-to-crosslinking-agent ratio of 1:(0.5–2) and a crosslinking time of 0.5–5 minutes would have amounted to optimization of known conditions to obtain the desired product.
Claim(s) 7-10 is/are rejected under 35 U.S.C. 103 as being unpatentable over Osuji (WO 2022/032236) as applied to claim 1 above, and further in view of Yue (“Activation of Peroxymonosulfate by Surfactants as the Metal-Free Catalysts for Organic Contaminant Removal”, 2017).
With respect to claim 7, the positively charged quaternary ammonium salt polymer catalyst of claim 1 has been discussed above.
Claim 7 further requires “a method for treating organic pollutants in water, comprising steps of: activating a peroxide by using a positively charged quaternary ammonium salt polymer catalyst to degrade organic pollutants in water; wherein the positively charged quaternary ammonium salt polymer catalyst is the positively charged quaternary ammonium salt polymer catalyst according to claim 1.” Osuji does not explicitly teach the limitations claimed above. However, Yue teaches treating water containing an organic dye by activating peroxymonosulfate with a positively charged long-chain quaternary-ammonium compound, particularly CTAB, thereby degrading the organic pollutant.
It would have been obvious to a person having ordinary skill in the art before the effective filing date of the invention to have, by the method of Osuji, substitute the polymerized quaternary-ammonium material of Osuji for the quaternary-ammonium surfactant of Yue in order to provide the quaternary-ammonium/peroxide interaction in a recoverable polymeric form (Yue 26069, abstract) (Yue 26076, Fig. 9) (Yue 26071-26073, Results and Discussion).
Regarding claim 8, preparation method according to claim 7 has been discussed above.
Claim 8 further requires “wherein the treatment specifically comprises: A) adding the positively charged quaternary ammonium salt polymer catalyst and a peroxide into water, wherein the peroxide degrades organic pollutants in the water after being activated by the positively charged quaternary ammonium salt polymer catalyst; or B) firstly adsorbing organic pollutants in water by using the positively charged quaternary ammonium salt polymer catalyst, and then degrading adsorbed organic pollutants by using the peroxide after being activated by the positively charged quaternary ammonium salt polymer catalyst.” Osuji does not explicitly teach the limitations above. However, Yue teaches adding the organic pollutant and the quaternary-ammonium catalyst to water and thereafter adding peroxymonosulfate to initiate degradation of the organic pollutant. Yue therefore teaches alternative A) of claim 8, namely adding the positively charged quaternary-ammonium catalyst and peroxide into pollutant-containing water such that the peroxide degrades the pollutant after activation by the catalyst (Yue 26071, Experimental Procedures).
Because claim 8 recites alternative A) or alternative B), the teachings of alternative A) is sufficient. It would have been obvious to substitute the polymerized quaternary-ammonium material of Osuji for Yue’s quaternary-ammonium surfactant for the reasons stated regarding claim 7. Therefore, the combination renders claim 8 obvious.
Regarding claim 9, the method of claim 7 has been discussed above.
claim 9 further requires “wherein the amount ratio of the positively charged quaternary ammonium salt polymer catalyst and the peroxide used is (0.05-20) g:(0.1-200) mmol.” Osuji does not explicitly teach the amount ratio of the positively charged quaternary ammonium salt polymer catalyst and the peroxide. However, Yue teaches conducting the catalytic oxidation using approximately 0.92 mM CTAB and approximately 0.25 mM peroxymonosulfate. Using the molecular weight of CTAB, 0.92 mmol of CTAB corresponds to approximately 0.335 g (Yue 26072, Fig. 2). The disclosed amount ratio is therefore approximately 0.335 g CTAB to 0.25 mmol peroxymonosulfate, which falls within the claimed amount ranges of (0.05–20) g:(0.1–200) mmol (Yue 26072, Fig. 1).
Upon substituting the polymerized quaternary-ammonium material of Osuji for Yue’s CTAB, it would have been obvious to use a catalyst/peroxide loading corresponding to the operative quaternary-ammonium and peroxide amounts taught by Yue. Yue teaches recognizes catalyst and peroxide concentrations as variables affecting pollutant-degradation performance. Accordingly, selection of an amount ratio within the extremely broad ranges recited in claim 9 would have been an obvious selection of workable catalyst and peroxide amounts.
It would have been obvious to substitute the polymerized quaternary-ammonium material of Osuji for Yue’s CTAB because Yue teaches catalyst/peroxide loading corresponding to the operating amount of quaternary-ammonium and peroxide as Yue further teaches catalyst and peroxide concentrations as variables affecting pollutant-degradation performance (Yue 26070, left col, Fig. 4) (Yue 26076, Fig. 9).
Regarding claim 10, the method of claim 7 has been discussed above.
claim 10 further requires “wherein the water has a pH value of 4-12.” Osuji does not explicitly teach wherein the water has a pH value of 4-12. However, Yue teaches conducting the CTAB/peroxymonosulfate treatment at an initial pH of approximately 7.0. A pH of 7.0 falls within the claimed pH range of 4–12 (Yue 26072, Fig. 2).
It would have been obvious to conduct the modified process employing the polymerized quaternary-ammonium material of WO ’236 at the same pH taught by Yue because the pH is suitable for Yue’s quaternary-ammonium/peroxymonosulfate oxidation process. Therefore, the combination renders claim 10 obvious.
Conclusion
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/STARFARI TESHAWN MCCLAIN/ Examiner, Art Unit 1736
/ANTHONY J ZIMMER/ Supervisory Patent Examiner, Art Unit 1736
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