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 .
Non-Final Rejection
The Status of Claims:
Claims 1-26 are pending.
Claims 1-26 are rejected.
DETAILED ACTION
1. Claims 1-26 are under consideration in this Office Action.
Priority
2. It is noted that this application is a 371 of PCT/US2023/024278 06/02/2023 , which is a continuation of 7805372 06/03/2022 PAT 11795153.
Drawings
3. None.
IDS
4. The IDS filed on 7/1/25, 7/16/25,4/17/26 are reviewed by the examiner.
Double Patenting
A rejection based on double patenting of the “same invention” type finds its support in the language of 35 U.S.C. 101 which states that “whoever invents or discovers any new and useful process... may obtain a patent therefor...” (Emphasis added). Thus, the term “same invention,” in this context, means an invention drawn to identical subject matter. See Miller v. Eagle Mfg. Co., 151 U.S. 186 (1894); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Ockert, 245 F.2d 467, 114 USPQ 330 (CCPA 1957).
A statutory type (35 U.S.C. 101) double patenting rejection can be overcome by canceling or amending the claims that are directed to the same invention so they are no longer coextensive in scope. The filing of a terminal disclaimer cannot overcome a double patenting rejection based upon 35 U.S.C. 101.
Claims 1, 5, 7-10, 17 are rejected under 35 U.S.C. 101 as claiming the same invention as that of claims 1, 4-6, 12, 14-15 of prior U.S. Patent No. 11,795,153. This is a statutory double patenting rejection.
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the claims at issue are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); and In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on a nonstatutory double patenting ground provided the reference application or patent either is shown to be commonly owned with this application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The USPTO internet Web site contains terminal disclaimer forms which may be used. Please visit http://www.uspto.gov/forms/. The filing date of the application will determine what form should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to http://www.uspto.gov/patents/process/file/efs/guidance/eTD-info-I.jsp.
Claims 1-4, 16, 18 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 3, 7-11, 13,16-19 of U.S. Patent No. 11,795,153 B1 .
Although the claims at issue are not identical, they are not patentably distinct from each other because of some difference between the scope of the claimed invention.
The claim 3 of U.S. Patent No. describes the following:
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, whereas the instant claims 1 and 4 do disclose the following method as shown below:
A process for preparing an epoxide, comprising:heating a mixture of a plurality of alkenes and a fatty acid at about 25 0C to about 100 0C;wherein a plurality of alkenes having following formula (I):R-CH=CH-R' (I) wherein R and R' are H or alkyl chains having 8 to 20 carbon atoms, adding an aluminum oxide catalyst to the reaction mixture;injecting hydrogen peroxide solution over a period of about 1 hour to about 48 hours into the reaction mixture;decanting the water from the reaction mixture; and collecting the epoxide.
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However, the instant claims differ from the U.S. Patent No. in that the scope of the claimed invention with respect to the specific limitation for the fatty acid formula(II) is separated unlike the claims of the U.S. Patent No.
Even so, it seems reasonable for the skilled artisan to separate the limitations of claim 3 into two portions in the claimed invention ; one claim is related to the process for preparing an epoxide, comprising: heating a mixture of a plurality of alkenes and a fatty acid, whereas the other one is dealt with the specific fatty acid formula(II) in the claim. Furthermore, reorganizing or rearranging or dividing the limitations of the claims can be considered as obvious variants over the patented claimed invention; there is very little difference as to the patentable distinction.
So, it would have been obvious to the skilled artisan to be motivated to divide those limitations into two different claims in order to emphasize some aspect of the claimed process. This is because the skilled artisan in the art would expect such a manipulation to be feasible and successful as guidance shown in the U.S.Patent No...
Claim Rejections - 35 USC § 103
2113 Product-by-Process Claims
PRODUCT-BY-PROCESS CLAIMS ARE NOT LIMITED TO THE MANIPULATION OF THE RECITED STEPS, ONLY THE STRUCTURE IMPLIED BY THE STEPS
“Even though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process.” In re Thorpe, 77 F.2d 695,698,227 USPQ 964, 966 (Fed. Cir. 1985) (citations omitted) (Claim was directed to a novolac color developer. The process of making the developer was allowed. The difference between the inventive process and the prior art was the addition of metal oxide and carboxylic acid as separate ingredients instead of adding the more expensive prereacted metal carboxylate. The product-by-process claim was rejected because the end product, in both the prior art and the allowed process, ends up containing metal carboxylate. The fact that the metal carboxylate is not directly added, but is instead produced in-situ does not change the end product.).
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.
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 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.
5. Claims 1 and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Stein et al (US 3,141,896) in view of Matsumoto et al (US 2012/0322706 A1)
Determination of the scope and content of the prior art
Stein et al discloses a method for the epoxidation of compounds having olefinic double bonds in the presence of an aluminum oxide catalyst and a fatty acid in the following examples :
A mixture of 290 g. of a C10-olefin fraction with a centrally located double bond (iodine number 87.6=1 mol of a mono-unsaturated compound), 30 g. of glacial acetic acid and 35 g. of aluminum oxide (prepared as described in Example 3) was treated at 75 ° C. by a dropwise addition of 68 g. of 50% hydrogen peroxide (1 mol) and, after 6 hours, by a further addition of 0.5 mol of H2O2 . The reaction product obtained after a total reaction time of 18 hours and following processing contained 3.7% epoxy oxygen and had an iodine number of 23.3. \Vhen the procedure was carried out without the addition of aluminum oxide, then there was obtained a reaction product with an epoxy oxygen content of 1.5% and 20 an iodine number of 40.6.
A mixture of 200 g. of soy oil (iodine number 128= l mol of a mono-unsaturated substance), 44 g. of butyric acid (0.5 mol) and 35 g. of aluminum oxide (prepared as described in Example 3) was treated at 75 ° C. by
addition thereto of 68 g. ( 1 mol) of 50% hydrogen peroxide and, after 6 hours, with further 0.5 mol of H202• After a total reaction time of 22 hours, the mixture
was processed as usual. There was obtained a soy oil epoxide with 2.7% epoxy oxygen content and an iodine number of 35.6. In a comparison procedure without any aluminum oxide addition, a soy oil epoxide was obtained which contained1.9% epoxy oxygen and had an iodine number of 50.2 (see col. 11 , examples 11-12).
The current invention, however, differs from the prior art in that the claimed lubricant composition prepared using the epoxidation process is unspecified in the prior art.
Matsumoto et al teaches that a lubricating oil composition of the invention significantly lowers wear and exhibits a stable low frictional coefficient (see abstract),;
Furthermore, in order to further improve the thermal and chemical stability when the lubricating oil composition of this embodiment is used as a refrigerating machine oil, it may contain one or more epoxy compounds selected from among phenyl glycidyl ether-type epoxy compounds, alkyl glycidyl ether-type epoxy compounds, glycidyl ester-type epoxy compounds, allyloxirane compounds, alkyloxirane compounds, alicyclic epoxy compounds, epoxidated fatty acid monoesters and epoxidated vegetable oils (see page 13, a paragraph#0161).
Ascertainment of the difference between the prior art and the claims
The difference between the current application and the applied Stein et al art is that the applied Stein et al art does not expressly teach the claimed lubricant composition prepared using the epoxidation process. The deficiency of the Stein et al is cured by the Matsumoto et al.
The difference between the current application and the applied Matsumoto et al art is that the Matsumoto et al does not expressly teach the claimed epoxidation preration by using an alkene and a fatty acid and an aluminum oxide catalyst . The deficiencies of the Matsumoto et al are cured by the Stein l et al.
Resolving the level of ordinary skill in the pertinent art.
Regarding Claim 20, Stein expressly discloses the process of claim 1, but does not disclose a lubricant composition prepared using the process. However, Matsumoto discloses lubricant composition (abstract) comprising epoxidated vegetable oils ( see page 13, a paragraph#0161). So, it would have been obvious to one with skill in the art to utilize the process disclosed by Stein, producing epoxidated vegetable oils; for use in lubricant compositions comprising the materials, as disclosed by Matsumoto.
Considering objective evidence present in the application indicating obviousness or nonobviousness.
Stein et al expressly discloses a method for the epoxidation of a C10-olefin compounds having a double bonds in the presence of an aluminum oxide catalyst and a the fatty acid, whereas Matsumoto et al teaches that a lubricating oil composition containing one or more epoxy compounds selected from allyloxirane compounds, alkyloxirane compounds significantly can lower wear and exhibit a stable low frictional coefficient (see abstract).
Both are closely related to each other with respect to the lubricant composition containing epoxide products and the epoxide product made by the particular epoxidation process.
So, If the skilled artisan had desired to produce a lubricant composition containing an epoxide in order to lower wear and exhibit a stable low frictional coefficient , it would have been obvious to the skilled artisan in the art before the effective filing date of the claimed invention to be motivated to utilize the process disclosed by Stein, producing epoxidated vegetable oils; for use in lubricant compositions comprising the materials, as disclosed by Matsumoto.
6. Claims 1-19 and 21-26 are rejected under 35 U.S.C. 103 as being unpatentable over Stein et al (US 3,141,896) in view of Goebbel et al (US 2006/0014970 Al ).
Determination of the scope and content of the prior art
Stein et al discloses a method for the epoxidation of compounds having olefinic double bonds in the presence of an aluminum oxide catalyst and a fatty acid in the following examples :
A mixture of 290 g. of a C10-olefin fraction with a centrally located double bond (iodine number 87.6=1 mol of a mono-unsaturated compound), 30 g. of glacial acetic acid and 35 g. of aluminum oxide (prepared as described in Example 3) was treated at 75 ° C. by a dropwise addition of 68 g. of 50% hydrogen peroxide (1 mol) and, after 6 hours, by a further addition of 0.5 mol of H2O2 . The reaction product obtained after a total reaction time of 18 hours and following processing contained 3.7% epoxy oxygen and had an iodine number of 23.3. \Vhen the procedure was carried out without the addition of aluminum oxide, then there was obtained a reaction product with an epoxy oxygen content of 1.5% and 20 an iodine number of 40.6.
A mixture of 200 g. of soy oil (iodine number 128= l mol of a mono-unsaturated substance), 44 g. of butyric acid (0.5 mol) and 35 g. of aluminum oxide (prepared as described in Example 3) was treated at 75 ° C. by
addition thereto of 68 g. ( 1 mol) of 50% hydrogen peroxide and, after 6 hours, with further 0.5 mol of H202• After a total reaction time of 22 hours, the mixture
was processed as usual. There was obtained a soy oil epoxide with 2.7% epoxy oxygen content and an iodine number of 35.6. In a comparison procedure without any aluminum oxide addition, a soy oil epoxide was obtained which contained1.9% epoxy oxygen and had an iodine number of 50.2 (see col. 11 , examples 11-12).
In addition, the aluminum oxide was produced by dehydration of a finely powdered alumin1.1m hydroxide at 400 ° C. up to a weight loss of 30% (see col. 9 example 3)
The current invention, however, differs from the prior art in that the claimed fatty acid having 5 carbon atoms to be reused, a continuous reactor, the agitation rate of the reactor, the flow rate of the reactor and soy oil contents are unspecified in the prior art.
Goebbel et al teaches a continuous process for the epoxidation of olefins by means of hydroperoxide as in claim 16, in which the epoxidation is carried out in a reactor in which at least one catalyst suspended in a liquid phase is present, wherein the liquid phase is passed through a device which has openings or channels and is installed in the reactor and the epoxide-containing liquid is separated off by means of crossflow filtration so that the suspended catalyst is retained in the reaction system.
Furthermore, the catalyst particles used in the process of the present invention preferably have a mean particle size of from 0.0001 to 2 mm, more preferably from 0.0001 to 1 mm, particularly preferably from 0.005 to 0.1 mm as in claims 8-9. Particles of this mean particle size surprisingly enable the relative velocity and mass transport to be increased further. (see page 1 , a paragraph#0016)
The process is simple to carry out. The abovedescribed device, preferably woven mesh packing or sheet metal packing, is installed in the reactor. The reaction mixture comprising olefin, hydroperoxide and suspension catalyst is then circulated at high velocity through the reactor by means of a pump. The throughput per unit cross-sectional area ( empty tube velocity) of the liquid phase is preferably from 50 to 300 m3/m2 h, in particular in the range from 100 to 250 m3 /m2 h.
Membranes suitable for the crossflow filtration are specifically treated aluminum oxide or sintered metal membranes having pore diameters of from 50 to 500 nm, preferably from 50 to 100 nm (see page 2, paragraphs#0024, 0026).
Examples of such organic compounds having at least one C-C double bond are the following alkenes: propene, 1-butene, 2-butene, isobutene, butadiene, pentenes, piperylene, hexenes, hexadienes, heptenes, octenes, diisobutene, trimethylpentene, nonenes, dodecene, tridecene, tetradecenes to eicosenes, tripropene(see page 2 , a paragraph#0032).
Ascertainment of the difference between the prior art and the claims
1. The difference between the current application and the applied art is that the applied art do not expressly teach the claimed particle size of the catalyst, the claimed agitation rate of the reactor, the flow rate of the reactor.
The difference between the current application and the applied Stein et al art is that the Stein et al does not expressly teach the claimed fatty acid having 5 carbon atoms to be reused, a continuous reactor, the agitation rate of the reactor, the flow rate of the reactor and soy oil contents. The deficiencies of the Stein et al are in part cured by the Goebbel et al.
3. The difference between the current application and the applied Goebbel art is that the Goebbel does not expressly teach the use of the fatty acid, the agitation rate of the reactor. The deficiencies of the Goebbel et al are in part cured by the Stein et al,.
Resolving the level of ordinary skill in the pertinent art.
Regarding the Claims 4,22,26, with respect to the lack of disclosing the claimed fatty acid having 5 carbon atoms to be reused, the prior art issinet about it . However, the prior art does mention the use of butyric acid during the epoxidation process (see col. 11 , example-12), which is similar to the well-known hexanoic acid compound with respect to its chemical structure; Furthermore, recycling the claimed fatty acid can be considered to be a part of the optimization of the process ,not as a patentable distinction over the prior art.
Moreover, the relationship between butyric acid and the known hexanoic acid compound are homologues to each other. Compounds that differ only by the presence or absence of an extra methyl group or two are homologues. Homologues are of such close structural similarity that the disclosure of a compound renders prima facie obvious its homologue. The homologue is expected to be preparable by the same method and to have generally the same properties. This expectation is then deemed the motivation for preparing homologues. Of course, these presumptions are rebuttable by the showing of unexpected effects, but initially, the homologues are obvious even in the absence of a specific teaching to add or remove methyl groups. See In re Wood, 199 USPQ 137; In re Hoke, 195 USPQ 148; In re Lohr, 137 USPQ 548; In re Magerlein, 202 USPQ 473; In re Wiechert, 152 USPQ 249; Ex parte Henkel, 130 USPQ 474; In re Fauque, 121 USPQ 425; In re Druey, 138 USPQ 39. In all of these cases, the close structural similarity between two compounds differing by one or two methyl groups was itself sufficient show obviousness. See also MPEP 2144.09, second paragraph.
So, if the skilled artisan in the art had desired to perform the epoxidation process by using an alkene compound and hexanoic acid as an alternative to butyric acid in the reaction mixture, it would have been obvious to achieve the similar successful result for the process.
Regarding the Claims 8-9, with respect to the lack of disclosing the claimed particle size of the catalyst, the use of the claimed agitation rate of the reactor, the flow rate of the reactor. Goebbel et al does mention that the particle size of the catalyst is in the range of from 0.0001 to 2 mm, more preferably from 0.0001 to 1 mm, From this information, it is reasonable for the skilled artisan in the art to have estimated roughly the particle of aluminum oxide indirectly.
Regarding the Claim 17, with respect to the lack of disclosing the agitation rate of the reactor, the prior art are silent about it. However, Goebbel et al does teach the use of the reactor in the continuous process for the epoxidation of olefins by means of hydroperoxide. This means that it is a natural procedure that the agitation rate in the reactor can be observed during the operation of the reactor. Furthermore, the limitation with respect to the agitation rate of the reactor does not impart patentability to the epoxidation process when such a value is one of those which would be determined or estimated by one of ordinary skill in the field of an epoxidation process using a reactor in achieving optimum operational condition for the reactor in the process. The agitation rate of the reactor is well-understood by those of ordinary skill in the art to be a result-effective variable, especially when attempting to control the effective outcome by selecting the optimum range of the agitation rate of the reactor. Therefore, it would have been obvious to the skilled artisan in the art to be motivated to control the optimum range of the agitation rate of the reactor. This is because the skilled artisan in the art would expect such a manipulation to be within the purview of the skilled artisan in the art.
Regarding the Claim 19, with respect to the lack of disclosing the flow rate of the reactor, Goebbel et al does mention at least indirectly that the throughput per unit cross-sectional area ( empty tube velocity) of the liquid phase is preferably from 50 to 300 m3/m2 h, in particular in the range from 100 to 250 m3/m2 h. From this information, it is reasonable for the skilled artisan in the art to have estimated or figured out roughly what the flow rate of the reactor can be by the given cross-sectional area of the reactor. This kind of procedure is a part of a routine work during the epoxidation process. Therefore, it is relevant to the prior art process.
Considering objective evidence present in the application indicating obviousness or nonobviousness.
Stein et al expressly discloses a method for the epoxidation of a C10-olefin compounds having a double bonds in the presence of an aluminum oxide catalyst and a the fatty acid. Similarly, Goebbel does teach the continuous process for the epoxidation of olefins such octene by means of hydroperoxide in a reactor.
Both prior art are closely associated with the epoxidation process by using octene or C10 olefin reactant under a similar reaction condition. Moreover, Goebbel does offer guidance that either octene or C10 olefin compound can be selected as the reactant for performing the epoxidation process.
So, if the skilled artisan in the art had desired to produce octene oxide from octene as an alternative , it would have been obvious to the skilled artisan in the art before the effective filing date of the claimed invention to be motivated to incorporate the teachings of Goebbel’s octene into the Mandelli epoxidation process in order to optimize the overall process. This is because the skilled artisan in the art would expect the combined processes to be successful and feasible as guidance shown in the prior art.
Conclusion
Claims 1-26 are rejected.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to TAYLOR V OH whose telephone number is (571)272-0689. The examiner can normally be reached 8:00-5:00.
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/TAYLOR V OH/Primary Examiner, Art Unit 1625 9/05/2026
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