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 .
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 01/07/2026 has been entered.
Priority
This application is a 371 of PCT/US20/66893 filed 12/23/2020 which claims benefit of provisional application 62/955,309 filed 12/30/2019. Applicant’s claim for the benefit of a prior-filed application under 35 U.S.C. 119(e) or under 35 U.S.C. 120, 121, 365(c), or 386(c) is acknowledged.
Acknowledgment is made of applicant’s claim for foreign priority under 35 U.S.C. 119 (a)-(d). based on FI20205067, filed on 01/23/2020. Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Status of the Claims
Claim 1 is amended. Claim 9 is cancelled.
Claims 1, 2, 4, 6, 11-14, 17-19 and 21-23 are pending (claim set as filed on 12/05/2025) and
are examined on the merits herein.
Withdrawal of Rejections
The response and amendment filed on 12/05/2025 are acknowledged. All of the amendment and arguments have been thoroughly reviewed and considered.
For the purposes of clarity of the record, the reasons for the Examiner's withdrawal and/or maintaining if applicable, of the substantive or essential claim rejections are detailed directly below and/or in the Examiner's response to arguments section.
Maintained/Modified Rejections
The following rejections are maintained and/or modified taking into consideration amendment to claim 1 filed on 12/05/2025.
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.
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.
Claims 1, 2, 4, 6, 11-14, 17-19 and 21-23 are rejected under 35 U.S.C. 103 as being unpatentable over Hakkarainen (WO 2019097123 A1) in view of Budde (US 20170247726 A1), Adedipe (Adedipe et al., J. Agric. Food. Chem., 2016, 64, 1850-1860), Kaastrup (Kaastrup et al. Polym. Chem., 2016, 7, 592-602), Yano (Yano et al. J. Ferment. Bioenerg., 1997, 84, 461-465), Eaton (WO 02095373 A1) and Olesberg (US 20150247794 A1).
Regarding claim 1, Hakkarainen teaches: “…a process for producing aqueous acrylamide solution by hydrating acrylonitrile in an aqueous solution in the presence of a biocatalyst.” (Abstract). The aqueous acrylamide solution is made by bioconversion in a reaction composed of water, biocatalyst and acrylonitrile: “…process for producing aqueous acrylamide solution comprising providing a slurry comprising water and a biocatalyst having Nitrile hydratase activity; feeding acrylonitrile into a reactor comprising said slurry to provide a reaction mixture comprising acrylamide, acrylonitrile and biocatalyst…” (p. 4, lines 9-14). The components of the reaction, i.e. biocatalyst, water and acrylonitrile, and steps to provide reaction mixture are the same as in claim 1 of instant application.
Hakkarainen teaches that the concentration of acrylonitrile and acrylamide and temperature of the reaction are monitored: “Course of the reaction is preferably monitored by on-line measuring at least one of the acrylonitrile and the acrylamide concentrations in the reactor, and preferably temperature of the reaction mixture. The monitoring and measuring may be performed with any suitable means and methods in the art.” (p. 7, lines 25-28). Hakkarainen teaches that the final concentration of acrylonitrile can be 1000 ppm or less: “…final concentration of the acrylonitrile is at most 1000 ppm, at most 100 ppm, a most 90 ppm, preferably at most 75 ppm, more preferably at most 50 ppm, and most preferably at most 10 ppm.” (p. 4, lines 28-30). Hakkarainen teaches regulation of the temperature of the reaction depending on concentration of acrylamide: “…cooling down of the reaction mixture … is started when acrylamide concentration reaches at least 27 wt%, preferably reaches 27 wt% to 38 wt%; cooling of the reaction mixture is continued so that when the acrylamide concentration reaches 37 wt% to 55 wt% …” (p. 4, lines 17-21). This concentration of acrylamide is within the range of claim 1.
Hakkarainen does not teach monitoring acrylonitrile and acrylamide with FTNIR spectroscopy, concentration of acrylonitrile measured with accuracy of at least 100 ppm and concentration of acrylamide measured with an accuracy of at least 5 wt% and concentrations of acrylonitrile and acrylamide measured by FTNIR using the recited wavelength and acquisition rate. HPLC method is used by Hakkarainen to measure concentrations of analytes, including acrylonitrile, acrylamide and acrylic acid: “The amount of residual acrylonitrile is measured by HPLC method, likewise concentrations of acrylamide and acrylic acid.” (p.10,lines 19-20). At the same time, as mentioned above, Hakkarainen suggests the use of any suitable methods known in the art for monitoring concentrations of components of the reaction. Hakkarainen does not teach positioning of an FTNIR probe in the reactor or outside of the reactor and the probe to comprise a transflection immersion probe. Hakkarainen does not teach production of aqueous acrylamide as an industrial process specifically.
Budde teaches methods of producing amide compound from nitrile compound with less acrylic acid as by-product using nitrile hydratase as a biocatalyst (Abstract). The preferred nitrile compound is acrylonitrile (paragraph 0028) and the amide compound is acrylamide (paragraph 0029). The method is developed to be used in industrial scale (paragraph 0065). The concentration of acrylonitrile is measured during production by on-line FTIR and adjusted to keep it at a constant level: “A constant concentration of acrylonitrile of 0.5 to 5 w/w % is adjusted by the use of an online Fourier Transform Infrared (FTIR) analysis, which directly communicates with the process control unit” (paragraph 0131). In Example 4 the concentration of acrylonitrile is kept constant at 1.0 +/- 0.1% and reaction is continued till acrylonitrile reaches 100 ppm: “The ACN concentration was measured by on-line FTIR, and the rate of addition of ACN was adjusted so that the ACN concentration in the reaction mixture was kept constant at 1.0±0.1% (w/w) until the entire ACN had been added to the reaction. The reaction was stopped after ACN concentration had decreased to <100 ppm due to conversion.” (paragraph 0125). Thus, the final concentration of acrylonitrile in Budde teaching is < 100 ppm, however, Budde does not explicitly describe measurement of acrylonitrile concentration of less than 1000 ppm (0.1%) by FTIR. Budde mentions that the amount of acrylamide is measured by HPLC (paragraph 0039).
Adedipe teaches measurement of acrylamide by NIR spectroscopy in French-fried potato (Abstract). Adedipe describes capturing spectra at 400-2500 nm and quantification of acrylamide with gas chromatography and mass spectrometry. Adedipe applied partial least-square (PLS) discriminant analysis and PLS modeling and demonstrated that NIR can accurately detect acrylamide content as low as 50 µg/kg (Abstract).
Kaastrup teaches monitoring of polymerization of poly(ethylene glycol) diacrylate hydrogels by UV-Vis and FTNIR (Abstract). Kaastrup discloses that monitoring includes quantifying the vinyl group conversion using vinyl group NIR overtone band (p. 3, last paragraph). Kaastrup describes that “the vinyl group concentration was determined by integrating the peak area between 6229 and 6128.8 cm−1 for the first overtone of the =C-H bond(s) associated with the acrylate group centered at 6180 cm−1 (1618 nm)” (p. 6, 1st paragraph). The acrylonitrile and acrylamide contain the same bond, i.e. =C-H bond and hence the same wavelength can be used for acrylonitrile and acrylamide measurement.
Yano teaches prediction of the concentrations of ethanol and acetic acid in fermentation broth based on NIR spectroscopy (Abstract). Yano showed that the raw NIR spectra of ethanol and acetic acid scanned at 800-2400 nm overlapped with each other and with water peaks at 1454 nm and 1940 nm (p. 463, left column, 1st paragraph, Figure 1). Yano mentioned that the peaks around 1700 nm may attribute to absorption of (C-H) stretch first overtone (p. 463, left column, 1st paragraph). Yano describes the correlation between the actual concentration of the analytes determined by gas chromatography and the second derivative values of NIR spectra analyzed by linear regression. Analysis revealed wavelengths for ethanol, i.e. 1686 nm, and for acetic acid, i.e. 1674 nm, that were not affected by the presence of the second analyte and were used for calibration (p. 463, right column, p. 464, left column, last paragraph and right column, 1st paragraph, Figure 3). Calibration equations were obtained and Yano discloses that an excellent agreement between the results of the conventional method of gas chromatography and NIR was observed for both analytes. These results indicated that concentrations of ethanol and acetic acid can be simultaneously analyzed by NIR (Abstract).
Eaton teaches infrared spectroscopy for on-line process control and endpoint detection (Title). Eaton describes that the concentration of the analyte can be determined using a mathematical model representing the relationship between the concentration of the analyte and the absorbance profile. The mathematical model can be developed by measuring the spectrum for a number of standard samples with known concentration and mathematically correlating the concentration as a function of absorbance profile using multivariant mathematical techniques referred as chemometrics (p. 17, lines 7- 14, 24-26). Eaton discloses that the preferred mathematical technique is PLS (Partial Least Squares) to model the spectra as a function of concentration. The concentration of the analyte being modelled in each standard is measured off-line by HPLC (p. 19, lines 11-13, 24-27). Eaton mentions that the developed chemometric model can be used to determine concentrations of analyte by FTIR measurement in real-time during continuous process and that allows to improve reaction control and more accurately determine the reaction end point (p. 21, lines 21-32). Eaton describes measurement of several analytes. Eaton discloses that the concentration of formaldehyde in the reaction mixture can be measured in the range of 250 ppm to 4500 ppm with a mean error of less than 55 ppm and even over a range of 100 ppm to 400 ppm with a mean error of 50 ppm (p. 22, lines 22-27).
Olesberg teaches a system and methods for continuous, real-time process monitoring and control by near-infrared (NIR) spectroscopy providing analysis of fluid streams (Abstract). The described system is designed to be used in laboratory and industrial settings (Abstract). Olesberg mentions that the off-line analysis by manual sampling can be accurate, but destructive, requires time, consumables and expensive hardware leading to insufficient sampling frequency to control the process (paragraph 0005). Olesberg discloses that NIR in his invention provides continuous and nondestructive quantification of constituents and materials in fluids which can be non-turbid to highly-turbid and no filtration is required (paragraph 0015). Olesberg mentions that NIR instruments provide scan times ranging from several hundred milliseconds to several seconds (paragraph 0010). Olesberg describes that the scan can be performed in less than 100 ms that provides scan averaging within the standard data collection time which is from one second to 10 minutes (paragraph 0048). Thus, Olesberg teaches acquisition rate from less than 100 ms to several seconds that includes the claimed range. Olesberg describes that measurements performed in real-time provide control of processes: “…measurements may be performed automatically, continuously, in real-time, and in the absence of an operator. Furthermore, certain embodiments of the present invention provide for feedback control of processes whereby one or more quantities of a substance in a process may be measured, and the measurement values used to automatically control desired values of the substance(s) in the process vessel.” (paragraph 0018).
Olesberg teaches positioning of optical probe in a bioreactor connected to the instrument by optical fibers: “… an optical probe 500 is installed within a vessel 100 such that optical elements within the optical probe 500 are in fluid contact with the contents of the vessel 100 during fluid processing. One or more optical fibers 510 connect the optical instrument 110 to the optical probe 500.” (paragraph 0055, Fig. 8). Olesberg describes that the optical probe is immersed in a fluid (paragraph 0061). Olesberg discloses that fluid sampling can be configured to operate in transmission and transflection optical geometry (paragraph 0061). For transflectional configuration: “… a portion of electromagnetic radiation incident on a fluid sample passes through said fluid sample and is directed back through the fluid sample to be collected generally in the incident direction, and a portion of the electromagnetic radiation reflects off the fluid sample and materials therein, and is collected generally in the incident direction“ (paragraph 0061). Thus, Olesberg teaches transflection immersion optical probe positioned in the reactor.
First, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify method of acrylamide synthesis described Hakkarainen by substituting HPLC as monitoring method with FTIR described by Budde for production of acrylamide in industrial setting. One would be motivated to make this modification because compared to HPLC, FTIR/FTNIR provides fast, sensitive and nondestructive method of detection which can be used for online control and adjustment of production as described by Budde. Applying FTIR/FTNIR for monitoring and regulating process of acrylamide production is advantageous because it will increase efficiency and reduce the cost of production. One would have reasonably expected success by this modification since both Hakkarainen and Budde teach methods of acrylamide synthesis by hydrolysis of acrylonitrile in the presence on nitrile hydratase.
Second, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to add determination of acrylamide by FTIR/NIR as described by Adedipe to method of acrylamide synthesis based on Hakkarainen and Budde teachings. One would be motivated to make this modification since Adedipe showed that NIR with applied PLS modeling can accurately detect acrylamide content as low as 50 µg/kg. One would have reasonably expected success by this modification because Hakkarainen, Budde and Adedipe teach determination of acrylamide by different methods.
Third, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to combine the teachings of Hakkarainen, Budde and Adedipe for production of acrylamide with monitoring via FTIR/FTNIR with teaching of Kaastrup and use the wavelength between 6229 and 6128.8 cm−1 to monitor the acrylonitrile and the acrylamide concentrations. One would have been motivated to do so because Kaastrup teaches detection of the first overtone of the =C-H bond by FTNIR at 6180 cm−1 and acrylonitrile and acrylamide contain the same bond. A skilled artisan would have reasonably expected success in the combination since Hakkarainen and Budde teach acrylonitrile measurement and Budde, Adedipe and Kaastrup describe application of FTNIR/FTIR/NIR to measurement of analyte concentrations.
Forth, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to follow Yano teaching and expect that acrylonitrile and acrylamide concentrations can be measured by FTNIR/FTIR/NIR in the same reaction process. One would have been motivated to do so because acrylonitrile and acrylamide have overlapping bands in NIR spectra and Yano teach that overlapping bands of other analytes, ethanol and acetic acid, can be resolved with calibration regression analysis and be simultaneously analyzed by NIR. A skilled artisan would have reasonably expected success in the that since Budde, Adedipe, Kaastrup and Yano describe application of FTNIR/FTIR/NIR to measurement of analyte concentrations.
Fifth, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to follow guidance of Eaton and apply chemometric modeling using PLS technique to measure concentrations of acrylonitrile and acrylamide by FTIR during acrylamide synthesis based on teachings of Hakkarainen, Budde, Adedipe, Kaastrup and Yano. One would have been motivated to do so because Eaton demonstrated that the modeling can be applied to real-time continuous process with monitoring by FTIR to improve reaction control and provides accuracy of less than 100 ppm. A skilled artisan would have reasonably expected success in the combination since Eaton, Budde, Adedipe, Kaastrup and Yano describe detection of analytes by FTIR and Hakkarainen, Budde and Eaton teach on-line monitoring of the analyte concentrations.
Lastly, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to position the transflection immersion FTIR/FTNIR probe in the reactor and use the acquisition time from 100 ms to several seconds per measurement as described by Olesberg for real-time monitoring and control of fluids in industrial setting by NIR for process of acrylamide synthesis based on Hakkarainen, Budde, Adedipe, Kaastrup, Yano and Eaton teachings. One would have been motivated to do so because Olesberg teaches the real-time control of the process and the FTIR/FTNIR probe can be connected with FTIR/FTNIR spectrometer via fiber optic cable allowing spectrometer to be placed far away from the reactor and positioning of the probe in the direct contact with the reaction components will increase speed and sensitivity of detection and provide continuous and robust operation as described by Olesberg. A skilled artisan would have reasonably expected success in the combination since Hakkarainen provided description of the process of synthesis of acrylamide from acrylonitrile in the presence of biocatalyst, Budde demonstrated application of FTIR for measurement of acrylonitrile concentration in acrylamide synthesis, Adedipe showed application of NIR for acrylamide measurement, Kaastrup provided wavelength for acrylonitrile and acrylamide measurement by FTNIR, Yano confirmed detection of analytes with overlapping spectra by NIR, Eaton described PLS modeling to measure analytes at low concentrations and high accuracy by FTIR and Olesberg described instrument and method for monitoring and controlling in real-time analytes concentrations with NIR transflection immersion probe positioned in the reactor in industrial settings.
Thus, combination of teachings of Hakkarainen, Budde, Adedipe, Kaastrup, Yano, Eaton and Olesberg renders claim 1 obvious.
Regarding claim 2, Hakkarainen teaches adjustment of the reaction process depending on the acrylonitrile conversion rate: “…the acrylonitrile feed rate is adjusted during the process to avoid acrylonitrile accumulation into the reaction mixture. The acrylonitrile is fed during the process with such a rate at which the acrylonitrile converts to acrylamide.” (p. 7, lines 29-31). Thus, Hakkarainen teaching in combination with Budde, Adedipe, Kaastrup, Yano, Eaton and Olesberg teachings renders claim 2 obvious.
Regarding claim 4, Hakkarainen teaches that the temperature of the reaction is maintained in the desired range by either cooling the mixture or heating the mixture (p. 7, lines 3-7). Budde teaches a cooling loop connected to the reactor: “ The hydration of acrylonitrile is generally carried out in a stirred tank reactor (rpm=250, volume V=4 L) with an external circulating loop for cooling.” (paragraph 0131).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to follow Budde teaching and use cooling loop connected to the reactor for reaction cooling. One would be motivated to do so with expected success because reaction of acrylamide production requires cooling to maintain required temperature as taught by Hakkarainen and Budde describes how it can be reached by cooling loop outside the reactor and both Hakkarainen and Budde teach acrylamide synthesis.
Regarding position of FTIR probe in the cooling loop, there could be only 2 possible positions for the immersion probe, i.e. in the reactor and in the external cooling loop since immersion probe requires to be immersed in the reaction mixture. It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to try each of the two possible positions for the probe and select the optimal one. One would be motivated to do so because optimal position of the FTNIR probe will increase efficiency of acrylamide synthesis and reduce cost of production. A skilled artisan would have reasonably expected success since FTNIR probe can be connected with the spectrometer with fiber optic cables allowing to position it in the reactor and in the external cooling loop and routine experimentation can be performed to select optimal probe positioning. Thus, Hakkarainen, Budde, Adedipe, Kaastrup, Yano, Eaton and Olesberg teachings render claim 4 obvious.
Regarding claims 6 and 19, Hakkarainen teaches that the concentration of acrylonitrile in the reaction mixture is maintained as less than 2% (p. 8, lines 1-2). Budde teaches production of acrylamide with on-line measurement of acrylonitrile with FTIR as described above. In Example 4 Budde describes that the concentration of acrylonitrile is kept constant at 1.0 +/- 0.1% (paragraph 0125) that covers limitations of claims 6 and 19.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention that the concentration of acrylonitrile can be maintained at less than 2% as taught by Hakkarainen and measured by FTIR with the accuracy of 0.1% as taught by Budde. One would be motivated to expect that with reasonable success because FTIR/FTNIR provides fast, sensitive and nondestructive method of detection which can be used for online control and adjustment of production as described by Budde. Applying FTIR/FTNIR for monitoring and regulating process of acrylamide production is advantageous because it will increase efficiency and reduce the cost of production. Thus, Hakkarainen, Budde, Adedipe, Kaastrup, Yano, Eaton and Olesberg teachings render claims 6 and 19 obvious.
Regarding claim 11, Hakkarainen teaches that “… 38 % to 48 % of total amount of acrylonitrile fed to the reactor is fed during 0 min to 60 min from the beginning of the process…” (p.9, lines 27-29). This statement is the same as in instant claim 11 and hence Hakkarainen teaching in combination with Budde, Adedipe, Kaastrup, Yano, Eaton and Olesberg teachings makes claim 11 obvious.
Regarding claim 12, Hakkarainen teaches that: “The reactor may be any suitable reactor, such as a semi-batch reactor, a continuous reactor, continuous reactors in series or stirred tank reactors I series, preferably a semi-batch reactor” (p. 9, lines 19-21). Thus, Hakkarainen teaching in combination with Budde, Adedipe, Kaastrup, Yano, Eaton and Olesberg teachings renders claim 12 obvious.
Regarding claim 13, Hakkarainen teaches that: “The biocatalyst may be any biocatalyst having Nitrile hydratase (NHase) activity known in the art. … the biocatalyst capable of converting acrylonitrile to acrylamide may be a microorganism which encodes the enzyme nitrile hydratase (NHase) or any part of said microorganism. ” (p. 5, lines 10-15). P. 5, lines 21-34 and p.6, lines 1-14 contain a list of microorganisms that can be used for the method of reference application which includes microorganisms in instant claim 13. The amount of biocatalyst used by Hakkarainen is: “… amount of the biocatalyst is 0.1 kg dry cells/m3 to 5 kg dry cells/m3 of reaction mixture” (p. 6, lines 15-16) which is the same as in instant application. Therefore, Thus, Hakkarainen teaching in combination with Budde, Adedipe, Kaastrup, Yano, Eaton and Olesberg teachings renders claim 13 obvious.
Regarding claims 14 and 23, Hakkarainen teaches monitoring and regulation of temperature. The following statements of Hakkarainen teaching cover instant claims 14 and 23 limitations:” The temperature of the reaction mixture is maintained at 15 to 25 °C. In one embodiment the temperature is maintained at 19 to 25°C, preferably at 20 to 22°C and most preferably at 22°C… the temperature is maintained in the desired range by measuring the temperature of the reaction mixture and either cooling the mixture or heating the mixture so that the temperature stays in the desired range” (p. 7, lines 3-7); “In one embodiment the cooling of said reaction mixture is started when acrylamide concentration reaches 28 wt% to 30 wt%... Cooling of the reaction mixture is continued so that when the acrylamide concentration reaches 37 wt% to 55 wt% the temperature of the reaction mixture is within range of 10 °C to 18 °C, or 10 °C to 21°C. ” (p. 8, lines 15-16, 21-24) and “ … the temperature of 18 °C to 25 °C is maintained for 30 min to 90 min, such as 45 min to 60 min” (p. 9, lines 23-24). Thus, Hakkarainen teaching in combination with Budde, Adedipe, Kaastrup, Yano, Eaton and Olesberg teachings renders claims 14 and 23 obvious.
Regarding claim 17, Hakkarainen teaches turbidity of reaction to be equal or less than 15: “In one embodiment the turbidity of the solution is equal or less than 15.” (p. 10, line 16) and hence Hakkarainen teaching in combination with Budde, Adedipe, Kaastrup, Yano, Eaton and Olesberg teachings renders claim 17 obvious.
Regarding claim 18 and 22, Hakkarainen teaches that during maturation phase unreacted acrylonitrile is used for acrylamide synthesis and maturation is monitored and continued: “… the maturation is continued until final concentration of the acrylonitrile in the reaction mixture is at most 1000 ppm, at most 100 ppm, at most 90 ppm, preferably at most 75 ppm, more preferably at most 50 ppm, and most preferably at most 10 ppm, or 0 ppm.” (p. 9, lines 8-12). Budde teaches that synthesis of acrylamide continues until the final concentration of acrylonitrile is below 100 ppm (paragraph 0125). Eaton provides chemometric modeling to measure low concentration of analytes by FTIR as described above for claim 1 (p. 21, lines 21-32, p. 22, lines 22-27).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention that during the maturation phase the concentration of acrylonitrile can be less than 1000 ppm as taught by Hakkarainen and the final concentration of acrylonitrile can be below 100 ppm as taught by Budde and that concentration can be measured by FTNIR/FTIR based on Eaton teaching. One would be motivated to expect that with reasonable success because Eaton demonstrated that the chemometric modeling can be applied to real-time continuous process with monitoring by FTIR to improve reaction control and provides accuracy of less than 100 ppm. Thus, Hakkarainen, Budde, Adedipe, Kaastrup, Yano, Eaton and Olesberg teachings render claims 18 and 22 obvious.
Regarding claim 21, Hakkarainen teaches regulation of the temperature of the reaction depending on concentration of acrylamide: “…cooling down of the reaction mixture … is started when acrylamide concentration reaches at least 27 wt%, preferably reaches 27 wt% to 38 wt%; cooling of the reaction mixture is continued so that when the acrylamide concentration reaches 37 wt% to 55 wt% …” (p. 4, lines 17-21). This concentration of acrylamide is within the range of instant application. Adedipe teaches that NIR can accurately detect acrylamide content (Abstract) as described for claim 1 above. Eaton provides chemometric modeling to measure low concentration of analytes by FTIR with accuracy of less than 100 ppm which corresponds to 0.01% (p. 21, lines 21-32, p. 22, lines 22-27) as described above for claim 1.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention that the concentration of acrylamide during the reaction can reach 37-55 wt% as taught Hakkarainen and can be measured by FTIR with the claimed accuracy. One would be motivated to expect that with reasonable success because Adedipe showed that acrylamide can be measured by NIR and Eaton demonstrated that the chemometric modeling can be applied to real-time continuous process with monitoring by FTIR to improve reaction control and provides accuracy of less than 100 ppm. Thus, Hakkarainen, Budde, Adedipe, Kaastrup, Yano, Eaton and Olesberg teachings render claim 21 obvious.
Response to Arguments
Applicant's arguments filed 12/05/2025 have been fully considered but they are not persuasive.
Applicant’s argues (addressing pages 7-10 of the Remarks) that Hakkarainen and Budde do not teach or suggest use of FTNIR for simultaneous determination of a concentration of acrylonitrile and a concentration of acrylamide and Budde is using FTIR for acrylonitrile and HPLC for acrylamide. Applicant further adds that FTIR peaks of acrylonitrile and acrylamide substantially overlap and application of separate techniques of Budde does not provide suggestion or motivation to use FTNIR for simultaneous measurement of acrylonitrile and acrylamide. These arguments are not persuasive because:
In response to applicant's arguments against the references individually, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986). In instant case, the rejection is based on the combination of references of Hakkarainen, Budde, Adedipe, Kaastrup, Yano, Eaton and Olesberg, wherein Hakkarainen provided description of the process of synthesis of acrylamide from acrylonitrile in the presence of biocatalyst (Abstract) and Budde demonstrated application of FTIR for monitoring acrylamide synthesis by measurement of acrylonitrile concentration (Abstract, paragraphs 0028, 0029, 0131). The newly added prior art of Adedipe showed application of NIR for acrylamide measurement (Abstract) providing motivation to include measurement of acrylamide during its synthesis. Kaastrup teaches wavelength for the first overtone of the =C-H bond in FTNIR spectra associated with the acrylate group centered at 6180 cm−1 (1618 nm)” (p. 6, 1st paragraph) providing motivation to use that wavelength for acrylonitrile and acrylamide measurement by FTNIR since they contain the same bond. Newly added prior art of Yano teaches detection of analytes, ethanol and acetic acid, by NIR in a region similar to instant application, i.e. around 1700 nm (which is 5882 cm-1), and mentions that the peaks around 1700 nm may attribute to absorption of (C-H) stretch first overtone (p. 463, left column, 1st paragraph). Although peaks for ethanol and acetic acid for C-H overtone are in the same region and overlap with each other, they can be resolved from each other as was shown by Yano by using regression analysis to identify peaks for each of them that was not affected by the presence of the second analyte (p. 463, right column, p. 464, left column, last paragraph and right column, 1st paragraph, Figure 3). Yano teaching of simultaneous detection of analytes with overlapping spectra by NIR provides motivation to apply the same technique for measurement of acrylonitrile and acrylamide with overlapping spectra in the same reaction process.
Applicant argues (addressing pages 10-14 of the Remarks) that claim 1 requires determination of distinct concentrations of acrylonitrile and acrylamide at about 5800-6200 cm-1 that overlaps with the water region at about 5900-7200 cm-1. Eaton teaches deconvolution avoiding the spectral region overlapping with water region and describes difficulties in quantification. Applicant points to overlapping of the spectral region of vinyl C-H overtones of acrylonitrile and acrylamide on Figure 1 of Application and argues that a skilled artisan would not expect to be able to use PLS to deconvolute overlapping spectral bands in a spectral region which overlaps the water region.
These arguments are not persuasive because: (i) In the citation from Eaton recited by the Applicant, Eaton mentions that "The glyphosate and formic acid could not be spectrally distinguished without a set of calibration samples to allow for spectral deconvolution." That indicates that deconvolution is possible by using calibration samples and modeling and hence the separate determination of concentrations of analytes is not excluded and (ii) Yano teaches detection of analytes with overlapping spectra as was discussed above. Besides, Yano discloses that the region of 1700 nm used for analyte detection is within the spectral region of water with the two main peaks for water at 1454 nm (6878 cm-1) and 1940 nm (5155 cm-1) (p. 463, left column and Figure 1). Nevertheless Yano describes simultaneous detection of both analytes by using regression analysis to identify peaks for each of them that was not affected by the presence of the second analyte and water interference.
Applicant argues (addressing pages 15-16 of the Remarks) that Olesberg fails to render obvious: “use of FTNIR at 5800-6200 cm-1 for simultaneous determination of a concentration of acrylonitrile with an accuracy of ± 100 ppm and a concentration of acrylamide with an accuracy of ± 5 wt%.”. Applicant further argues (addressing pages 16-19 of the Remarks) that Kaastrup teaches combined concentration of PEGDA and VP determined from the overlapping vinyl C-H bands of the acrylate groups of each molecule. Applicant points to Figure 4 of Kaastrup showing overlapping of PEGDA and VP peaks with each other and with water region. Applicant argues that Kaastrup provides no indication that deconvolution is possible and additionally is silent regarding detection limits and accuracy of the analytical methods used.
Arguments regarding simultaneous detection of acrylonitrile and acrylamide and preventing interference of spectra with water region based on Olesberg and Kaastrup teachings are not persuasive because current rejection is based on combination of references and these arguments were addressed above. Regarding detection limits and accuracy of detection, Eaton teaches that the PLS chemometric modeling can be applied to measure analytes in the real-time continuous process with monitoring by FTIR that allows to improve reaction control and more accurately determine the reaction end point (p. 17, lines 7- 14, 24-26, p. 18, lines 17-19, p. 21, lines 27-32) and describes measurement of several analytes with accuracy of less than 100 ppm (p. 22, lines 22-27) providing motivation to apply chemometric modeling using PLS technique to measure concentrations of acrylonitrile and acrylamide by FTIR during acrylamide synthesis to reach lower detection limits with high accuracy.
Therefore, the 35 U.S.C. 103 rejection is maintained and modified necessitated by amendment of claims 1.
Conclusion
No claims are allowed.
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/L.G.K./Examiner, Art Unit 1653
/SHARMILA G LANDAU/Supervisory Patent Examiner, Art Unit 1653
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