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 Objections
Claim 2 objected to because of the following informalities: in line 3 “compound is dihydroxy” should read “compound is a dihydroxy”. Appropriate correction is required.
Claim Rejections - 35 USC § 112
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.
Claim 7 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 7, the recitation “between 0.005 N and 0.0005 N” is unclear because claim 6 already recited the more-narrow range of “0.005 N and 0.0001 N”; claim 7 is dependent on claim 6 and therefore inherits all of its claim limitations. When a narrow range is claimed and a broader range is then claimed afterwards, it creates confusion as to the intended scope of the claim. See MPEP 2173.05(c). Furthermore, dependent claims must further narrow the scope of the claimed invention, and, in this case, dependent claim 7 broadens the scope of the claimed invention when compared to claim 6. See MPEP 608.01(n)(III).
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.
Claim(s) 1-4, 6-8, 10 is/are rejected under 35 U.S.C. 103 as being unpatentable over Wenbin (CN113866246A)(references herein made with respect to English Machine Translation) in view of Esteban (Journal of the Institute of Brewing, Vol. 128, pg. 171-187, 26 October 2022) further in view of Guo et al. (Chinese Chemical Letters, Vol. 26, pgs. 357-360, 14 November 2014).
Regarding claim 1, Wenbin teaches a method of measuring trace acids ([n0005]) (invention provides a method for determining the trace acid value of photo-induced acid-producing agents). Wenbin further teaches:
mixing an alkaline inorganic compound and at least a part of an organic solvent to form a titration liquid ([n0006]-[n0007]) ((1)Prepare a 0.005-0.01 mol/L NaOH or KOH solution… (2) Measure or prepare the same volume of the same solvent),
wherein an equivalent concentration of the alkaline inorganic compound in the titration liquid is not greater than 0.005 N ([n0006]-[n0007]) ((1) Prepare a 0.005-0.01 mol/L NaOH or KOH solution)
implementing a test sample preparing process that includes: mixing a compound to be measured and at least another part of the organic solvent to form a test sample ([n0009]) (Add the photoacid-producing agent sample to the solvent in step (2) and disperse it evenly to obtain photoacid-producing agent sample solution. The weight ratio of photoacid-producing agent sample to solvent is 1:10-200.)
using the titration liquid to perform an acid-base potentiometric titration on the test sample to analyze a residual acid content of the diol compound ([n0009]) (Then perform potentiometric titration with NaOH or KOH titrant prepared in step (1) and obtain the curve. Calculate the total acid content)
using an organic solvent for the titration liquid and test sample that will not react with the acid that is being measured ([n0025]) (the solvent used in step (2) is an organic solvent that is liquid at room temperature and pressure, and the organic solvent does not react with the free acid)
accounting for impurities in the solvent by running a “blank” sample with the solvent and a known amount of acid ([n0008]) ((3) Blank determination: Weigh 5-10 free acid standard samples… use the solvent described in step (2)… perform potentiometric titration on the free acid solution… Calculate the amount of acid in the blank).
Wenbin further teaches of using ethanol as an organic solvent for testing the amount of acid in a sample ([n0003]) (GB/T264-83 specifies acid value testing for products, using 0.05N potassium hydroxide, 95% ethanol, and Basic Blue 6B as reagents).
Wenbin is silent to analyzing a diol compound and providing an organic solvent and placing the organic solvent into a distillation apparatus to distill the organic solvent and obtain a distilled liquid; wherein the organic solvent preparing process includes excluding an initial fraction consisting of at least initial 10% of the distilled liquid distilled from the distillation apparatus, and collecting a middle fraction of the distilled liquid distilled from the distillation apparatus, so as to obtain a purified organic solvent.
In the analogous art of removing impurities from organic solvents, Esteban teaches a method of using distillation to obtain purified ethanol (pg. 172 right column second paragraph) (57 volatile compounds from five chemical families (alcohols, esters, aldehydes, acids, and terpenes) diluted in an ethanol-water matrix… distillation using a laboratory column). Esteban teaches of excluding an initial fraction consisting of at least initial 10% of the distilled liquid and collecting a middle fraction of the distilled liquid (pg. 173 starting at left column first paragraph) (head and tail fractions were put aside). See also figure 1A:
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Esteban teaches that this fractional distillation method is advantageous because aldehyde impurities are present in the initial fractions (pg. 179 left column second paragraph) (aldehydes are at a maximum concentration at the beginning of distillation), and high boiling point acids are present in the terminal fractions (pg. 179 right column second paragraph) (Most acids are concentrated in the tail and residue fractions
(Figures 7A and 7B). This is explained by their low volatility).
It would have been obvious to a person having ordinary skill in the art before the effective filing date of the instant application to modify Wenbin’s method of accounting for impurities in the organic solvent by first distilling the organic solvent and excluding an initial fraction consisting of at least initial 10% of the distilled liquid and collecting a middle fraction of the distilled liquid as taught by Esteban because it would lead to the predictable outcome of removing the aldehyde and high boiling point acid impurities that are present in the initial and final fractions of the distillation with a reasonable expectation of success (see [n0008] of Wenbin; see pg. 173 left-right column and pg. 179 of Esteban). See MPEP 2143(I)(G).
Wenbin in view of Esteban is silent to mixing a diol compound to form a test sample.
In the analogous art of detecting residual acids in an analyte via titration, Guo teaches a method of analyzing the dihydroxy aromatic compound of dopexamine dihydrochloride via titration (abstract) (synthesis of dopexamine dihydrochloride… no unacceptable ion was brought to the final product… The titration purity of the final product was more than 99.5%). Accordingly, the prior art references teach that it is known that dopexamine dihydrochloride and photo-induced acid-producing agents are elements that are known in the art to be able to be analyzed by titration to determine their purities.
It would have been obvious to a person having ordinary skill in the art before the effective filing date of the instant application to substitute the photo-induced acid-producing agents of Wenbin in view of Esteban with the dopexamine dihydrochloride diol compound of Guo because both elements were known equivalents for substrates to be analyzed by titration (see [n0005] of Wenbin and abstract of Guo). The substitution would have resulted in the predictable result of quantifying the residual acid content of the diol compound with a reasonable expectation of success. See MPEP 2143(I)(B).
Regarding claim 2, Wenbin in view of Esteban further in view of Guo teaches the method of claim 1 as rejected above. Wenbin in view of Esteban further in view of Guo teaches:
wherein the organic solvent is ethanol ([n0003] of Wenbin or pg. 172 right column second paragraph of Esteban) (acid value testing… using 0.05N potassium hydroxide, 95% ethanol… as reagents or an ethanol-water matrix… distillation using a laboratory column),
the alkaline inorganic compound is potassium hydroxide ([n0006]-[n0007] of Wenbin) ((1) Prepare a 0.005-0.01 mol/L NaOH or KOH solution), and
the diol compound is dihydroxy aromatic compound (abstract of Guo) (synthesis of dopexamine dihydrochloride… The titration purity of the final product was more than 99.5%).
Regarding claim 3, Wenbin in view of Esteban further in view of Guo teaches the method of claim 1 as rejected above. Wenbin in view of Esteban further in view of Guo teaches excluding the initial fraction consisting of the distilled liquid distilled from the distillation apparatus and excluding a final fraction consisting of a final fraction of the distilled liquid (pg. 173 starting at left column first paragraph of Esteban) (head and tail fractions were put aside). Wenbin in view of Esteban further in view of Guo teaches that the initial fraction to be excluded is 10-15% of the distilled liquid (mass of ‘heads’ ~15 g; ~12% of total, Figure 2B of Esteban), the percentage of the final fractions to be excluded are ~38% of the distilled liquid (mass of ‘tail’ ~50 g; 38%, Figure 2B of Esteban), and the middle portion accounts for the remaining 10% to 15% up to 90% to 95% of the distilled liquid (mass of ‘heart’ ~75 g; ~50%, Figure 2B of Esteban), see Figure 2B for mass values (circles):
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Wenbin in view of Esteban further in view of Guo teaches that the percentage of the final fractions to be excluded is a result-effective variable; excluding a final fraction consisting of ~38% of the distilled liquid achieved the desired outcome of removing aldehydic and high boiling point acid impurities from the ethanol (pg. 179 left column second paragraph of Esteban and right column second paragraph of Esteban) (aldehydes are at a maximum concentration at the beginning of distillation and Most acids are concentrated in the tail and residue fractions (Figures 7A and 7B). This is explained by their low volatility)). As such, lowering the volume of the final fraction to be excluded would lead to a larger volume of purified ethanol to be collected.
Wenbin in view of Esteban further in view of Guo is silent to excluding a final fraction that consists of a final 5% to 10% of the distilled liquid.
It would have been obvious for a person having ordinary skill in the art before the effective filing date of the instant application to try excluding a final fraction that consists of a final 5% to 10% of the distilled liquid because the percentage of the distilled liquid to be discarded is a result-effective variable that can be lowered through routine optimization to lead to the predictable outcome of removing aldehydic and high boiling point acid impurities and increasing the yield of purified ethanol with a reasonable expectation of success (pg. 179 left column second paragraph of Esteban). See MPEP 2144.05(II).
Regarding claim 4, Wenbin in view of Esteban further in view of Guo teaches the method of claim 3 as rejected above. Wenbin in view of Esteban further in view of Guo teaches:
wherein the initial fraction of the distilled liquid distilled from the distillation apparatus includes a low boiling point aldehyde compound (pg. 179 left column second paragraph of Esteban) (aldehydes are at a maximum concentration at the beginning of distillation), and
the final fraction of the distilled liquid distilled from the distillation apparatus includes a high boiling point acid compound (pg. 179 right column second paragraph of Esteban) (Most acids are concentrated in the tail and residue fractions (Figures 7A and 7B). This is explained by their low volatility).
Regarding claim 6, Wenbin in view of Esteban further in view of Guo teaches the method of claim 1 as rejected above. Wenbin in view of Esteban further in view of Guo teaches the equivalent concentration of the alkaline inorganic compound in the titration liquid is between 0.005 N and 0.0001 N ([n0006]-[n0007] of Wenbin) ((1) Prepare a 0.005-0.01 mol/L NaOH or KOH solution). Note that for NaOH or KOH normality (N) is synonymous with molarity (mol/L).
Regarding claim 7, Wenbin in view of Esteban further in view of Guo teaches the method of claim 6 as rejected above. Wenbin in view of Esteban further in view of Guo teaches the equivalent concentration of the alkaline inorganic compound in the titration liquid is between 0.005 N and 0.0005 N ([n0006]-[n0007] of Wenbin) ((1) Prepare a 0.005-0.01 mol/L NaOH or KOH solution). Note that for NaOH or KOH normality (N) is synonymous with molarity (mol/L).
Regarding claim 8, Wenbin in view of Esteban further in view of Guo teaches the method of claim 1. Wenbin in view of Esteban further in view of Guo teaches a weight ratio of diol compound and the organic solvent in the test sample as being from 1:10 to 1:200 ([n0009] of Wenbin) (The weight ratio of photoacid-producing agent sample to solvent is 1:10-200). Wenbin in view of Esteban further in view of Guo teaches that the ratio of diol and the organic solvent is a result-effective variable because a weight ratio of diol compound and the organic solvent from 1:10 to 1:200 achieved the desired outcome of accurately and reliably measuring the acid content of the diol compound ([n0027] of Wenbin) (By selecting appropriate detection reagents and conditions, the determination results of trace acid values are more accurate and reliable). Increasing the concentration of the diol compound would reasonably allow for the use of less organic solvent.
Wenbin in view of Esteban further in view of Guo does not teach a weight ratio of diol compound and the organic solvent being 1:1 to 1:4.
It would have been obvious before the effective filing date of the instant application to try a weight ratio of diol compound and the organic solvent of 1:1 to 1:4 because the weight ratio is a result-effective variable that can be adjusted through routine experimentation to lead to accurately and reliably quantifying the acid content in a diol compound while using less organic solvent with a reasonable expectation of success ([n0027] of Wenbin). See MPEP 2144.05(II).
Regarding claim 10, Wenbin in view of Esteban further in view of Guo teaches the method of claim 1 as rejected above. Wenbin in view of Esteban further in view of Guo teaches wherein the titration process is performed by a potentiometric titration method ([n0009] of Wenbin) (perform potentiometric titration with NaOH or KOH titrant prepared in step (1)).
Claim(s) 5 is/are rejected under 35 U.S.C. 103 as being unpatentable over Wenbin (CN113866246A) in view of Esteban et al. (Journal of the Institute of Brewing, Vol. 128, pg. 171-187, 26 October 2022) further in view of Guo et al. (Chinese Chemical Letters, Vol. 26, pgs. 357-360, 14 November 2014), as applied to claim 1, further in view of Borys (Organometallics, Vol. 42, pgs. 182-196, 29 January 2023).
Regarding claim 5, Wenbin in view of Esteban further in view of Guo teaches the method of claim 1 as rejected above. Wenbin in view of Esteban further in view of Guo teaches of purifying organic solvent via distillation (pg. 172 right column second paragraph of Esteban) (in an ethanol-water matrix… distillation using a laboratory column).
Wenbin in view of Esteban further in view of Guo does not disclose purging the organic solvent with a nitrogen gas for 10 minutes to 30 minutes, and then distilling the organic solvent under an atmosphere filled with the nitrogen gas.
In the analogous art of purifying organic solvents, Borys discloses a method of purging the organic solvent with a nitrogen gas (pg. 182 right column last paragraph) (inert gas typically nitrogen or argon [open parenthesis removed for clarity]) for approximately 10 minutes prior to distilling the organic solvent under a nitrogen atmosphere (pg. 193 left column second paragraph) (Attached to the distillation flask containing the crude liquid under a flow of inert gas… After several minutes, the temperature… is slowly increased until the distillation begins). Borys teaches that this approach serves to degas the solution and remove any residual volatile impurities or unwanted solvents (pg. 193 left column second paragraph) (This serves to degas the crude liquid and remove any residual solvent or volatile impurities).
It would have been obvious before the effective filing date of the instant application to modify the distillation of organic solvent as taught by Wenbin in view of Esteban further in view of Guo by first purging the organic solvent with nitrogen gas for 10 minutes then distilling the organic solvent by the distillation apparatus under an atmosphere filled with nitrogen gas because it would lead to the predictable outcome of degassing the organic solvent and removing residual volatile impurities or unwanted solvents with a reasonable expectation of success (see pg. 172 right column second paragraph of Esteban; see pg. 193 left column second paragraph of Borys). See MPEP 2143(I)(G).
Claim(s) 9 is/are rejected under 35 U.S.C. 103 as being unpatentable over Wenbin (CN113866246A) in view of Esteban (Journal of the Institute of Brewing, Vol. 128, pg. 171-187, 26 October 2022) further in view of Guo et al. (Chinese Chemical Letters, Vol. 26, pgs. 357-360, 14 November 2014), as applied to claim 1 above, further in view of Zhang (Nitrogen purged titration system Standard Operating Procedure, University of Illinois Urbana-Champaign, 2 December 2017). Note that references to Guo are made using the Machine Translated version that is provided.
Regarding claim 9, Wenbin in view of Esteban further in view of Guo teaches the method of claim 1 as rejected above. Wenbin in view of Esteban further in view of Guo teaches of analyzing the diol compound (see abstract of Guo) via potentiometric acid-base titration to determine the residual acid content ([n0009] of Wenbin) (Then perform potentiometric titration).
Wenbin in view of Esteban further in view of Guo is silent to using a nitrogen gas to purge the test sample before analyzing the residual acid content of the diol compound.
In the analogous art of methodizing acid-base titrations, Zhang teaches a method of purging the analyte with nitrogen gas prior to performing the titration in order to remove CO2 from the liquids to be used in the titration (pg. 2 Section 3 and Section 4) (prepare titration samples in beakers and transfer them into a glovebox… purge glovebox for several hours before titration to remove CO2). Accordingly, the prior art references teach all of the claimed elements.
The combination of the known elements is achieved by a known method of first purging the test sample using nitrogen gas and then performing the acid-base titration. Furthermore, all the claimed elements would continue to operate in the same manner. Specifically, this ordering of the steps would have led to the removal of CO2 from the test sample and analyzing the residual acid content of the diol compound.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the instant application to purge the test sample with nitrogen as taught by Zhang before analyzing the residual acid content of the diol compound as taught by Modified Wenbin as being no more “than the predictable use of prior-art elements according to their established functions” to lead to the predictable outcome of removing CO2 from the liquid to be titrated with a reasonable expectation of success (see pg. 2 of Zhang and [n008]-[n009] of Wenbin). See MPEP 2143(I)(A).
Conclusion
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/H.D.C./Examiner, Art Unit 1758
/MARIS R KESSEL/Supervisory Patent Examiner, Art Unit 1758
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