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 .
DETAILED ACTION
Claim Status
Claims 1-2, 4-10, and 12-15 are pending. Claims 1-2 and 4-10 are under examination. Claims 1-2 and 4-10 are rejected. No claims allowed.
Election/Restrictions
Claims 12-15 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 07/07/2025.
Filing Receipt
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Response to Amendments/Arguments
Applicant's amendments and arguments filed 10/25/2025 are acknowledged and have been fully considered. The Examiner has re-weighed all the evidence of record. Any rejection and/or objection not specifically addressed below in original or modified form is herein withdrawn.
The below modified 103 rejection of claims 1-2, and 4-10 over Jones et al., Cho et al., Schreier et al. and as evidence by Hong Kong constitutes the complete set of rejections and/or objections presently being applied to the instant application.
Response to Arguments
Applicant's arguments filed 10/25/2025 have been fully considered but they are not persuasive.
Applicant argues:
“The cited references, taken alone or in combination, do not disclose or suggest each and every element of the claim” (claim 1). See page 6 of remarks.
“Jones does not disclose or suggest "removing unreacted alcohol from the reaction mixture such that the content of unreacted alcohol becomes 5 wt% or less," as recited in claim 1”. See page 6 of remarks.
Examiner’s response:
The removal of the alcohol to the currently claimed weight percent was taught by Cho et al. See page 5 of the non-final mailed 07/29/2025.
Applicant argues:
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Examiner’s response:
Jones et al. taught the simultaneous neutralization and hydrolysis in step c (columns 4-5). See page 4 of the non-final mailed 07/29/2025.
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Concerning the high temperatures and pressures, the limitations of high temps. and pressures are not claimed limitations.
Concerning the claimed temperatures of 150 to 190C and the pressure of 3 bar, these limitations were argued to be arrived at by routine experimentation. See page 7 of the non-final mailed 07/29/2025.
Concerning the lack of a cooling process as currently claimed, the rejection of record recited the ordinary artisan would have excluded separate cooling processes between steps 1 to 3 to conserve energy. See page 7 of the non-final mailed 07/29/2025. As recited in the rejection of record page 5, Cho et al. teach the importance of temperature conservation when cooling the ester reaction mixture to ensure less energy consumption (page 84).
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Applicant argues:
Schreier does not cure the deficiencies of Jones and Cho. Rather, Schreier merely discloses cooling the temperature to about 110 °C or below during the step of catalytic hydrolysis and neutralization after removing the alcohol ( col. 7).
Examiner’s response:
Schreier was not utilized to teach the temperatures and/or pressures.
Applicant argues:
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Examiner’s response:
The limitation of 5 wt% was addressed in the original rejection and in the above arguments. The temperatures and pressures were argued to be arrived at by the ordinary artisan by routine experimentation. Concerning the lack of a cooling process as currently claimed, the rejection of record recited the ordinary artisan would have excluded separate cooling processes between steps 1 to 3 to conserve energy.
For the reasons stated above the obviousness rejection is maintained/modified as set forth below.
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.
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) 1-2 and 4-10 are rejected under 35 U.S.C. 103 as being unpatentable over Jones et al. (US Patent 5,324,853, Patent date 06-1994), Cho et al. (KR900008130, Published 1990. Machine translation attached. Cited in IDS filed 08/12/2022), Schreier et al. (US Patent 6,150,552, 11-2000) and as evidence by Hong Kong (2 pages, Published 2015). The modifications were necessitated by amendment.
Scope of the Prior Art
Jones et al. teach the following (columns 4-5).
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Concerning the base in claim 6, Jones et al. teach the preferred base being sodium carbonate (column 18).
Concerning claim 8, Jones et al. teach aromatic acids, phthalic, isophthalic and terephthalic acids (column 7, lines 30-55).
Concerning claim 9 and the C5-C20 aliphatic alcohols, Jones et al. teach C1-C30 monohydric alkanols, and n-dodecanol (column 8, lines 5-20).
Concerning claim 10 and the catalyst, Jones et al. teach tetra-isopropyl titanate (TITP) (column 12, Lines 1-15).
Ascertain the Differences
Jones et al. does not teach the removal of alcohol immediately prior to the simultaneous neutralization and hydrolysis step.
Secondary References
Cho et al. teach removal of alcohol to 0.5 wt% or less prior to any neutralization and hydrolysis step (page 84, near middle of page).
Cho et al. teach the importance of temperature conservation when cooling the ester reaction mixture to ensure less energy consumption (page 84).
Cho et al. teach the importance of preventing filtration difficulties linked to hydrolysis of the titanium metal catalyst and formation of a gelatinous phase (page 83, bottom).
Cho et al. and Jones et al. teach overlapping subject matter and are considered
analogous art to the invention because both teach esterifying carboxylic acids with excess alcohol to prepare esters (Cho et al. page 84, near middle of page).
Concerning claim 7 and step 4 being conducted by a decompression process, Cho et al. teach removal of trace amounts of alcohol and moisture from the ester and teach inert gas is introduced into the ester layer and distillation is performed under reduced pressure (page 86).
Schreier et al. was brought in to teach the benefit for removing alcohol prior to
the hydrolysis of a titanate catalyst. Removal of the alcohol after hydrolysis results in solids that cause fouling in the distillation column (column 7, lines 35 to bottom).
Schreier et al. teach overlapping subject matter to Jones et al. with respect to
preparing alkyl terehalophthalate esters made from the acid and alcohol (Schreier et al. column 3, lines 5-15). Note: Jones et al. teach the acids may be halogenated (column 7, lines 30-45).
Schreier et al. is considered analogous art to the invention for teaching a solution
to the problem of solid generation during the hydrolysis of the claimed catalysts. See specification page 23 and aggregated or gelled catalyst and residues).
Temperature and pressure aide in the increase of a reaction rate as evidence by Hong Kong (bridging pages 1-2).
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have combined the prior art to arrive at the current invention with a reasonable expectation of success.
It would have been obvious to have firstly removed the alcohol to 5 wt% or less as taught by Cho et al. prior to the simultaneous hydrolysis and neutralization taught by Jones et al.
The ordinary artisan knowing the problem with filtering caused from the gelatinous phase formed during the hydrolysis of titanium catalysts taught by Cho et al. would have opted to remove alcohol prior to the hydrolysis step to prevent the fouling taught by Schreier et al. Being motivated by the teachings by Schreier et al. to remove the alcohol first to avoid fouling, the ordinary artisan would have arrived at the current invention.
Concerning the temperature of 150C to 250C in the current step 2, and the
exclusion of a separate cooling process between steps 1 to 3 in claim 11, the ordinary artisan understanding the conservation of energy and the lack thereof when using excessive cooling taught by Cho et al., would have arrived at the claimed reaction mixture temperature of step 2 via routine experimentation and would have excluded
separate cooling processes between steps 1 to 3 to conserve energy.
Concerning the claimed temperature and pressure of 150 to 190C or more and 3 to 10 bar or more in claims 1, and 4, reaction rates are enhanced and increased by temperature and pressure as evidence by Hong Kong (bridging pages 1-2). Thus, arriving at the claimed temperatures and pressures through routine experimentation to enhance the reaction rates of the hydrolysis reaction would have been obvious.
Concerning the time in claim 5, reaction times can be adjusted to arrive at
working ranges through routine experimentation. For example, not enough time and the reaction does not even initiate and/or go to completion. The ordinary artisan knowing a hydrolysis reaction needs to take place, would have arrived at the claimed times to ensure the hydrolysis reaction went to completion.
MPEP 2144.05 II. A. and B. “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).
Conclusion
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the
examiner should be directed to BLAINE G DOLETSKI whose telephone number is (571)272-2766. The examiner can normally be reached M-F 7-4 EST.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at (571)270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/B.G.D/Examiner, Art Unit 1692 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625
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