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 .
Status of the Application
Claims 1-20 are pending.
Election/Restrictions
Applicants’ election with traverse of Group I, claims 1-14, in the reply filed on 09/09/2026 is acknowledged. The election was made with traverse.
The traversal is on the ground(s) that the inventions as grouped shares a common special technical feature over the cited prior art. This is not found persuasive, please see the rejection as set forth below. Therefore, there is no special technical feature connecting the Groups.
Claim(s) 15-20 have been withdrawn from consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or a linking claim.
The requirement is still deemed proper and is therefore made FINAL.
Please note that after a final requirement for restriction, the Applicants, in addition to making any response due on the remainder of the action, may petition the Commissioner to review the requirement. Petition may be deferred until after final action on or allowance of claims to the invention elected, but must be filed not later than appeal. A petition will not be considered if reconsideration of the requirement was not requested. (See § 1.181.).
Applicant is reminded that upon the cancellation of claims to a non-elected invention, the inventorship must be amended in compliance with 37 CFR 1.48(b) if one or more of the currently named inventors is no longer an inventor of at least one claim remaining in the application. Any amendment of inventorship must be accompanied by a request under 37 CFR 1.48(b) and by the fee required under 37 CFR 1.17(i).
Claims 1-14 are under current examination.
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 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 of this title, 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 text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
The factual inquiries set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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 1-14 are rejected under 35 U.S.C. 103 as being unpatentable over Tirtowidjojo (US 8558029 B2) and IP (IP.com Journal, 2009, 9(6A), 13) in combination.
Determining the scope and contents of the prior art
Tirtowidjojo teaches same method of making of phenolic glycol ethers, such as ethylene glycol phenyl ether, propylene glycol ether, dialkylene phenolic glycol ether using same reactants phenols and ethylene oxide or propylene oxide in presence of Lewis base (encompass alkali hydride) with examples of NaOH and KOH (entire application). Since the process described in the cited prior art is same as in the instant specification (see below)
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the glycosylated phenol impurities formed during the process, 2-hydroxyphenylethanol, 4-hydroxyphenylethanol (formed when phenol is treated with ethylene oxide), 2-hydroxyphenylpropanol, 4-hydroxyphenylpropanol (formed when phenol is treated with propylene oxide) are also same as in the instant application and as also evidenced from the instant application paragraphs 0002-0005 as reproduced above (entire application). The cited prior art further teaches purification using distillation (encompass thin layer evaporation) of ethylene glycol phenyl ether, propylene glycol ether, dialkylene phenolic glycol ether (heavier fractions) from the glycosylated phenol impurities, and water (lighter fraction) and how adjustment of levels of base, such as NaOH favors mono (ethylene glycol phenyl ether, propylene glycol ether),and di product ratios dialkylene phenolic glycol ether in purified streams containing NaOH with less than 1wt% of glycosylated phenol impurities (see figure 1A, mono and di product from 12 having no glycosylated phenol impurities):
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The cited prior art teaches presence of water in the mixture and a dehydrating step to remove a portion of water from the phenolic glycol product (entire article and figures). Since the impurities of the cited prior art are same and are present in presence of NaOH (same as in the instant claims), the impurities are expected to form same salt as in the instant claims whether recognized by the cited prior art. Further, since the impurities in the cited prior art product mixture is same as in the instant claims, the boiling point of impurities is expected to satisfy limitation of the instant claim 12.
In the same field of endeavor, Ip teaches purification of glycol ethers heavy streams (obtained from treating phenol and alkylene oxide and base catalyst NaOH, KOH, same method as in the instant specification and Tirtowidjojo) to obtain higher order alkoxylates, i.e., di, tri etc. using base NaOH, KOH using thin film evaporation (entire article). Ip teaches advantages of using thin film evaporation to avoid heat related decomposition impurities (entire article)
Ascertaining the differences between the prior art and the claims at issue
Tirtowidjojo teaches same method of making of phenolic glycol ethers, such as ethylene glycol phenyl ether, propylene glycol ether, dialkylene phenolic glycol ether using same reactants phenols and ethylene oxide or propylene oxide in presence of Lewis base (encompass alkali hydride) with examples of NaOH and KOH and purification using distillation to same purity as in the instant claims, but fails to teach thin film evaporation and amount of base in the heavy stream.
Ip teaches purification of glycol ethers heavy streams (obtained from treating phenol and alkylene oxide and base catalyst NaOH, KOH, same method as in the instant specification and Tirtowidjojo) to obtain higher order alkoxylates, i.e., di, tri etc. using base NaOH, KOH using thin film evaporation (entire article). Ip teaches advantages of using thin film evaporation to avoid heat related decomposition impurities but fails to teach amount of base in the heavy stream.
Resolving the level of ordinary skill in the pertinent art
Thus, with the guidance provided by the combination of Tirtowidjojo and IP, a person of ordinary skill in the art would have been motivated to use thin film evaporation of heavy stream in presence of base to obtain purified form dialkylene phenolic glycol ether to avoid impurities due to excessive heat and decomposition.
With regards to the amount of base- Tirtowidjojo teaches that amount of base may be adjusted depending on desired amount of mono/diproduct ratio. Thus, it would have been prima-facie obvious to a person of ordinary skill in the art that depending on desired product stream, amount of base may be adjusted. Thus, the cited prior art meets limitation of the instant claims.
Based on the above established facts, it appears that the combination of teachings of above cited prior art read applicants’ process.
Therefore, all the claimed elements were known in the prior art and one skilled person in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination would have yielded predictable results to one of ordinary skill in the art at the time of the invention.
Considering objective evidence present in the application indicating obviousness or nonobviousness
To establish a prima facie case of obviousness, three basic criteria must be met: (1) the prior art reference must teach or suggest all the claim limitations; (2) there must be some suggestion or motivation, either in the references themselves or in the knowledge generally available to one of ordinary skill in the art, to modify the reference or to combine reference teachings; and (3) there must be a reasonable expectation of success; and (MPEP § 2143).
In this case, Tirtowidjojo teaches same method of making of phenolic glycol ethers, such as ethylene glycol phenyl ether, propylene glycol ether, dialkylene phenolic glycol ether using same reactants phenols and ethylene oxide or propylene oxide in presence of Lewis base (encompass alkali hydride) with examples of NaOH and KOH and purification using distillation to same purity as in the instant claims and Ip teaches purification of glycol ethers heavy streams (obtained from treating phenol and alkylene oxide and base catalyst NaOH, KOH, same method as in the instant specification and Tirtowidjojo) to obtain higher order alkoxylates, i.e., di, tri etc. using base NaOH, KOH using thin film evaporation (entire article). Ip teaches advantages of using thin film evaporation to avoid heat related decomposition impurities.
So, the combination of prior art read applicants claims.
In KSR International Vo. V. Teleflex Inc., 82 USPQ2d (U.S. 2007), the Supreme Court particularly emphasized “the need for caution in granting a patent based on a combination of elements found in the prior art,” (Id. At 1395) and discussed circumstances in which a patent might be determined to be obvious. Importantly, the Supreme Court reaffirmed principles based on its precedent that “[t]he combination of familiar elements according to known methods is likely to be obvious when it does no more than yield predictable results.” (Id. At 1395). See MPEP 2143 - Examples of Basic Requirements of a Prima Facie Case of Obviousness [R-9].
In this case at least prong (E) “Obvious to try” – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success would apply.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense. In that instance the fact that a combination was obvious to try might show that it was obvious under § 103.”KSR, 550 U.S. at ___, 82 USPQ2d at 1397. If any of these findings cannot be made, then this rationale cannot be used to support a conclusion that the claim would have been obvious to one of ordinary skill in the art. Further, there is a reasonable expectation of success that dialkylene phenolic glycol ether may be purified from heavy stream using base, such as NaOH and thin film evaporation and can be made by combination of the above cited prior art.
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention by taking advantage of the teaching of the above cited references and to make the instantly claimed process with a reasonable expectation of success. Modifying such parameters is prima facie obvious because an ordinary artisan would be motivated to develop an alternative process for economic reasons or convenient purposes from a known individual reaction steps, and to arrive at applicants’ process with a reasonable expectation of success, since it is within the scope to modify the process through a routine experimentation.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to PANCHAM BAKSHI whose telephone number is (571)270-3463. The examiner can normally be reached M-Thu 7-4.30 EST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Milligan Adam can be reached at 571-2707674. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/PANCHAM BAKSHI/Primary Examiner, Art Unit 1623
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