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 Claims
The amendment filed on 05/08/2026 has been entered. Claims 1-10 have been amended and claims 11-20 have been newly added. Thus claims 1-20 are currently pending and are under examination.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 17-18 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
Claims 17-18 have been newly added to recite “a recovery rate, based on the isobutyl vinyl ether, in a range of from 73.7 to 85.7 mass %” and “a recovery rate, based on the isobutyl vinyl ether, of at least 85.7 mass %”, respectively. However, the instant specification appears devoid of such description regarding the entire range of the claimed recovery rate. The specification only supports the recovery rate of 85.7 mass % (pg. 22, para. [0034]) and 73.7 mass % *pg. 23, para. [0035]) but fails to disclose, either explicitly or implicitly, the entire range of from 73.7 to 85.7 mass % or of at least 85.7 mass %.
Thus, at the time the application was filed, a skilled artisan would not recognize from the disclosure that Applicant was in possession of the limitations “a recovery rate, based on the isobutyl vinyl ether, in a range of from 73.7 to 85.7 mass %” and “a recovery rate, based on the isobutyl vinyl ether, of at least 85.7 mass %”.
MPEP § 2163.06 notes: " If new matter is added to the claims, the examiner should reject the claims under 35 U.S.C. 112(a) or pre-AIA 35 U.S.C. 112, first paragraph - written description requirement. In re Rasmussen, 650 F.2d 1212, 211 USPQ 323 (CCPA 1981)"
MPEP § 2163.02 states that “Whenever the issue arises, the fundamental factual inquiry is whether the specification conveys with reasonable clarity to those skilled in the art that, as of the filing date sought, applicant was in possession of the invention as now claimed. See, e.g., Vas-Cath, Inc. v. Mahurkar, 935 F.2d 1555, 1563-64, 19 USPQ2d 1111, 1117 (Fed. Cir. 1991). An applicant shows possession of the claimed invention by describing the claimed invention with all of its limitations using such descriptive means as words, structures, figures, diagrams, and formulas that fully set forth the claimed invention. Lockwood v. Am. Airlines, Inc., 107 F.3d 1565, 1572, 41 USPQ2d 1961, 1966 (Fed. Cir. 1997). Possession may be shown in a variety of ways including description of an actual reduction to practice, or by showing that the invention was "ready for patenting" such as by the disclosure of drawings or structural chemical formulas that show that the invention was complete, or by describing distinguishing identifying characteristics sufficient to show that the applicant was in possession of the claimed invention. See, e.g., Pfaff v. Wells Elecs., Inc., 525 U.S. 55, 68, 119 S.Ct. 304, 312, 48 USPQ2d 1641, 1647 (1998); Regents of the Univ. of Cal. v. Eli Lilly, 119 F.3d 1559, 1568, 43 USPQ2d 1398, 1406 (Fed. Cir. 1997); Amgen, Inc. v. Chugai Pharm., 927 F.2d 1200, 1206, 18 USPQ2d 1016, 1021 (Fed. Cir. 1991) (one must define a compound by "whatever characteristics sufficiently distinguish it").”
MPEP § 2163.06 further notes " When an amendment is filed in reply to an objection or rejection based on 35 U.S.C. 112(a) or pre-AIA 35 U.S.C. 112, first paragraph, a study of the entire application is often necessary to determine whether or not "new matter" is involved. Applicant should therefore specifically point out the support for any amendments made to the disclosure."
This is a new matter rejection.
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 1-10 stand rejected and claims 11-20 are newly rejected under 35 U.S.C. 103 as being unpatentable over Patent application publication number US2010/0249465A1 (US’465; cited in IDS 07/24/2023).
Regarding claims 1-2 and 6, US’465 teaches a method for producing high-purity vinyl ether which comprises:
a first step; a vinyl ether synthesis step of subjecting an alcohol (I) represented by the general formula (1)
R—O—H (1)
(wherein R is an aliphatic hydrocarbon group or an alicyclic hydrocarbon group), to a vinyl ether formation reaction in the presence of a catalyst to synthesize a vinyl ether (II) represented by the general formula (2)
R—O—CH═CH2 (2)
(wherein R is an aliphatic hydrocarbon group or an alicyclic hydrocarbon group),
wherein the vinyl ether formation reaction is an addition reaction of an alcohol to acetylene;
a second step; a catalyst removal step of removing the catalyst from the reaction mixture obtained in the first step to obtain a crude vinyl ether containing the vinyl ether (II) and the unreacted raw material alcohol (I);
a third step; an acetal formation step of reacting the unreacted raw material alcohol (I) in the crude vinyl ether, with the vinyl ether (II) in the presence of an acid catalyst, to convert the alcohol (I) and vinyl ether (II) into an acetal (III) represented by the general formula (3)
PNG
media_image1.png
168
825
media_image1.png
Greyscale
(wherein R is an aliphatic hydrocarbon group or an alicyclic hydrocarbon group); and
a fourth step; a distillation and purification step of subjecting a crude vinyl ether containing the acetal (III) to distillation to obtain a high-purity vinyl ether ([0014]-[0020] and [0023]).
As specific examples of the aliphatic hydrocarbon group, there can be mentioned straight chain or branched chain alkyl groups such as ethyl group, n-propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, neopentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, 2-ethylhexyl group and the like; alkyl groups having cycloalkyl substituent, such as cyclohexylmethyl group, tricyclodecanylmethyl group, 1-adamantylmethyl group and the like; and straight chain or branched chain alkenyl groups such as allyl group, isopropenyl group, butenyl group, pentenyl group, hexenyl group, heptenyl group, and octenyl group ([0036]).
Regarding claims 2-3 and 15-16, the reference further teaches neutralizing and/or removing the acid catalyst after the acetal formation reaction, wherein the acid catalyst by the addition of a basic compound ([0029] and [0075]).
Regarding claim 4, US’465 teaches the first step is conducted in the presence of an alkali metal alcoholate catalyst ([0057]-[0058]).
Regarding claim 7, the reaction of the first step is conducted in the presence of an organic solvent such as amide solvents, sulfur-containing solvents and glycol dialkyl ether solvents ([0059]).
Regarding claims 8-9, the reaction of the first step in US’465 is conducted at a reaction temperature is ordinarily 80 to 200° C and at a reaction pressure of 0.3 MPa or lower ([0060]).
Regarding claim 10, US’465 teaches that the acid catalyst is selected from inorganic acids such as sulfuric acid, nitric acid, hydrochloric acid, phosphoric acid and the like; organic acids such as carboxylic acid, organic sulfonic acid and the like; and solid acid catalysts such as acidic zeolite, heteropoly-acid, and strongly acidic ion exchange resin ([0067]).
Regarding claim 19, US’465 teaches the distillation column comprises theoretical plate number of 1-20 ([0080]).
Regarding claims 1-2 and 6, the difference between US’465 and the instant claim is that the instant claim is drawn to a method for producing isobutyl vinyl ether using isobutyl alcohol whereas US’465 teaches a method for producing vinyl ether using alcohol comprising an aliphatic hydrocarbon group selected from a number of straight chain or branched chain alkyl groups, including the instantly claimed isobutyl alcohol group.
However, a skilled artisan would have had reason to try the alcohol of US’465 with the limited number of aliphatic hydrocarbon groups, including the isobutyl group as instantly claimed, with a reasonable expectation of success in obtaining vinyl ether that also includes isobutyl vinyl ether.
MPEP § 2143 states that the Supreme Court in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) identified a number of rationales to support a conclusion of obviousness which are consistent with the proper “functional approach” to the determination of obviousness as laid down in Graham and discussed circumstances in which a patent might be determined to be obvious. Importantly, the Supreme Court reaffirmed principles based on its precedent that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp and that a combination was obvious to try might show that it was obvious under § 103.”KSR, 550 U.S. at 421, 82 USPQ2d at 1397. Therefore, choosing from a finite number of identified, predictable solutions, is likely to be obvious when it does no more than predictable results and with a reasonable expectation of success.
Furthermore, the claimed process differs from the process of US’465 in the pressure of step (A3). In the reference, the distillation of the fourth step is conducted at a pressure of 0.1 to 13.3 kPa ([0080]). However, the claimed pressure range of 40 kPaA to atmospheric pressure (101.32 kPa) and of 80 kPaA to atmospheric pressure are merely close to that of US’465. According to MPEP § 2144.05, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close absent any showing of unexpected results or criticality. In this instance, the current specification describes that the process produces a high-purity IBVE having a purity of 99 mass% or more (pg. 22). Similarly, US’465 teaches a high-purity vinyl ether of 99 mass % or higher can be obtained efficiently ([0079]). As such, due to the absence of evidence indicating that conducting the distillation step at a pressure of 40 kPaA (or 80 kPaA) to atmospheric pressure is critical over that of the prior art, the difference in pressure does not support the patentability of subject matter encompassed by the prior art.
Regarding claims 11-14, US’465 also fails to teach the recited overhead temperature and bottom temperature of the distillation column. However, such claimed temperatures would be within the purview of a skilled artisan. It is understood that a distillation column operates with a temperature gradient, wherein the temperature at the top is the coldest and highest at the bottom. The specific temperatures at the overhead position and the bottom position are governed by the product composition, the column’s pressure and vapor-liquid principles. In this instance, the skilled artisan would have been motivated in determining, based on the boiling point of the components in the product mixture, the optimal overhead and bottom temperatures of the distillation column through routine optimization and would arrive at the instantly claimed temperatures with a reasonable expectation of success in separating the acetal product and obtaining the vinyl ether at a high purity.
Regarding claims 17-18, US’465 further teaches that a high-purity vinyl ether of 99 mass % or higher in purity can be obtained efficiently ([0079]). The reference however is silent the method having the recovery rate as instantly claimed. However, since every limitation of instantly claimed method is obvious over the teachings of US’465, in which (1) isobutyl alcohol is listed as one of the starting materials and (2) the distillation pressure in step (A3) is merely close to the claimed one, there is a prima facie case of obviousness for US’465 to have the recovery rate based on the isobutyl vinyl ether as instantly claimed.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct a method for producing isobutyl vinyl ether as instantly claimed in view of the teachings of US’465.
Response to Arguments
Applicant argues that US’465 fails to teach the pressure recited in step (A3) and that there is no motivation to modify the pressure of US’465 to the claimed one.
The examiner disagrees. The Office Action already indicated that due to the pressure of the instant claims and that of the reference being merely close, modifying the pressure of the reference to that of the instant claims would yield nothing more than the predictable removal of the acetal. There is no evidence or criticality of using the instantly claimed pressure. In fact, the instant invention produces isobutyl vinyl ether at a purity of 99% and the same purity is obtained in US’465.
Furthermore, there is a high difference in boiling points between isobutyl vinyl ether (82-83 °C) and acetaldehyde diisobutyl acetal (171.30 °C) at atmospheric pressure of 760 mmHg. A skilled artisan would thus have been motivated in conducting distillation at atmospheric pressure in order to separate acetaldehyde diisobutyl acetal from isobutyl vinyl ether.
Additionally, conducing a distillation process under vacuum, which also includes the instantly claimed 40 kPa to less than atmospheric pressure, is also a known process to the skilled artisan in order to lower the boiling points of the materials to be separated, thus preventing thermal degradation by decreasing the temperature of the distillation process.
As such, absent any evidence of unexpected results or criticality of using the claimed pressure, the prima facie obviousness of the instant claims is maintained for reasons of record.
Conclusion
Claims 1-20 are rejected and no claims are allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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 MEDHANIT W BAHTA whose telephone number is (571)270-7658. The examiner can normally be reached Monday-Friday 8am-5pm.
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.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/MEDHANIT W BAHTA/Primary Examiner, Art Unit 1692
Prosecution Insights