DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claims 1, 19 and 20 are pending as amended on 11/3/2025.
The rejection below has been modified solely to address the new limitation which has been added to claim 1. Therefore, this action is properly made final.
Any rejections and/or objections made in the previous Office action and not repeated below are hereby withdrawn. The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office Action.
Claim Rejections - 35 USC § 103
Claim(s) 1, 19 and 20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Behr et al (Catalytic Processes for the Technical Use of Natural Fats and Oils, Chem. Eng. Technol. 2008, 31, No. 5, 700–714) in view of Mubima et al (US 2015/0336873) and Annoot et al (FR 3009554; English equivalent US 2016/0185705 cited herein).
Behr teaches catalytic processes using natural fats and oils (title). Behr teaches that oleic acid is the most frequently occurring unsaturated fatty acid (p 701, lower left), and that it is very important as feedstock in the technical conversion of fats and oils (p 701, upper right). Behr teaches that main processing steps start with a cleavage of the structure of triglycerides to glycerol and fatty acid, which can be done by transesterification with methanol to methyl esters, and then separating the fatty chain mixtures (p 701, middle right). Behr teaches metathesis has been applied in oleochemistry for many years already (p 710, first paragraph of section 3.4), and that in cross-metathesis, a fatty substrate reacts with e.g., a petrochemical alkene (p 710, lower left). Behr discloses the cross-metathesis of oleic acid methyl ester with ethene as as an example of cross-metathesis to produce 1-decene and 9-decenoic acid methyl ester (p 710, lower right text) and teaches that 9-decenoic acid methyl ester can be converted into 10-aminodecanoic acid methyl ester, which can be used to produce nylon-10 (p 711, figure 21 and upper left column):
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Behr’s disclosed process, as described above, comprises many steps which correspond to, or substantially correspond to, presently claimed steps:
Behr teaches providing a methyl ester of 9-decenoic acid by deriving the methyl ester of 9-decenoic acid from a methyl ester of unsaturated natural fatty acid (figure 21). The methyl ester of unsaturated natural fatty acid shown in Behr’s figure 21 is oleic acid methyl ester, which comprises a carbon-carbon double bond between the ninth and tenth carbon atoms from the ester group (including the carbon in the carbonyl of the ester, as set forth in [0047] of the instant specification).
Behr teaches reacting the methyl ester of the unsaturated natural fatty acid with a short-chain alpha-olefin (ethene) in the presence of a metathesis catalyst (ruthenium carbene) (p 710) to form methyl ester of 9-decenoic acid and 1-decene (figure 21, p 711) [which meets the corresponding metathesis reaction steps recited in claim 1, except that Behr fails to name “unsaturated triene having at least one terminal carbon-carbon double bond” as an alternative petrochemical alkene to ethene, and fails to name a solid or slurried metathesis catalyst comprising a molybdenum and/or tungsten complex.]
Behr teaches “follow-up chemistry” to form the methyl ester of 10-aminodecanoic acid from the methyl ester of 9-decenoic acid (figure 21) [However, Behr fails to teach the specific follow up chemical reactions required to form the methyl ester of 10-aminodecanoic acid from the methyl ester of 9-decenoic acid, and therefore, Behr fails to teach that the disclosed methyl ester of 10-aminodecanoic acid is formed by reaction of the disclosed methyl ester of 9-decenoic acid with brominating agent, followed by a reaction with aminating agent.]
Behr teaches that 10-aminodecanoic acid leads to nylon-10 (p 711, upper left column) [which corresponds to the presently recited “polymerizing” step recited in claim 1].
Given that Behr shows conversion of 9-decenoic acid methyl ester to 10-aminodecanoic acid methyl ester in figure 21, and further given Behr’s subsequent teaching that 10-aminodecanoic acid (rather than the methyl ester precursor shown in the figure) leads to nylon-10, one having ordinary skill in the art would have recognized that the follow-up chemistry required to produce nylon-10 from 10-aminodecanoic acid methyl ester shown in Behr’s figure 21 requires converting Behr’s depicted 10-aminodecanoic acid methyl ester to Behr’s disclosed 10-aminodecanoic acid [which corresponds to the presently recited “converting” step in claim 1], followed by Behr’s disclosed step of polymerizing 10-aminodecanoic acid to form nylon-10 (i.e., polyamide-10).
As set forth in the above discussion, there are differences between the presently claimed process (of making polyamide-10 from a natural oil via cross-metathesis of natural fatty acid ester) and the process disclosed by Behr (of making polyamide-10 from a natural oil via cross-metathesis of a natural fatty acid ester). However, in view of the teachings of Mubima and Annoot, as set forth in the following discussion, the claimed process would have been obvious.
As to the recitation of an “unsaturated triene” as the short-chain alpha olefin in the metathesis reaction with the methyl ester of unsaturated natural fatty acid:
As set forth in the discussion above, Behr teaches (fig 21) the cross metathesis of methyl oleate utilizing ethylene as a short chain olefin. Behr fails to disclose short chain olefin alternatives to ethylene.
Mubima teaches that olefin metathesis provides one possible means to convert certain natural oil feedstocks into olefins and esters that can be used in a variety of applications [0083]. Mubima teaches that when the metathesis uses short-chain olefins and the natural oil includes esters of oleic acid, an amount of 1-decene and 1-decenoid acid (or ester thereof) are formed [0087]. Mubima discloses reaction of natural oil feedstock in the presence of a metathesis catalyst, and discloses that the natural oil or unsaturated ester undergoes a cross-metathesis reaction with low molecular weight or mid-weight olefin [0089]. Like Behr, Mubima teaches ethylene as a low molecular weight olefin [0090]. Mubima further teaches that “low molecular weight olefin” may also refer to dienes or trienes, and names 1,4,7-octatriene as an example low molecular weight olefin [0025].
Considering that Mubima teaches the same general metathesis reaction disclosed by Behr (cross-metathesis of ester of oleic acid with a low molecular weight olefin to produce 1-decene and decenoic acid ester), and further considering that Mubima names ethylene along with many alternative examples of low molecular weight olefins, one having ordinary skill in the art would have reasonably predicted that the low molecular weight olefin disclosed by Behr (ethylene) could be substituted with another low molecular weight olefin named by Mubima (such as 1,4,7-octatriene) with a reasonable expectation of successfully obtaining a cross-metathesis product mixture comprising the desired products disclosed by Behr (1-decene and 9-decenoic acid methyl ester).
Case law has established that it is prima facie obvious to substitute one known element for another to obtain predictable results. KSR Int'l Co. v. Teleflex, Inc., 550 U.S. 398 (2007). MPEP 2143, rationale (B). It would have been obvious to the person having ordinary skill in the art, therefore, to have carried out the cross-metathesis of oleic acid methyl ester to produce 1-decene and 9-decenoic acid methyl ester, as disclosed by Behr, by substituting the low molecular weight olefin named by Behr (ethylene) for another compound (e.g., 1,4,7-octatriene) named as an example of a low molecular weight olefin in art (Mubima) which similarly discloses the cross metathesis of oleic acid ester with a low molecular weight olefin (1,4,7-octatriene has a terminal carbon-carbon double bond).
As to the presently recited metathesis catalyst:
As set forth in the discussion above, Behr discloses cross metathesis utilizing ruthenium carbene as a metathesis catalyst. Behr fails to teach alternative catalysts, such as catalysts comprising molybdenum and/or tungsten complexes, and fails to teach that the catalyst is slurried with or added in a solid state form to the natural oil or the unsaturated natural fatty acid esters.
Mubima discloses that metathesis reactions can employ any suitable metathesis catalyst [0105]. Like Behr, Mubima teaches metathesis catalysts which include ruthenium carbene [0106]. Mubima further teaches that in some embodiments the metathesis catalyst includes a molybdenum and/or tungsten carbene complex, or a molybdenum and/or tungsten containing alkylidene complex [0107]. Mubima also teaches that the metathesis catalyst can be slurried with the natural oil or unsaturated ester in order to eliminate solvent from the process, and eliminate downstream olefin losses when separating solvent. Mubima also teaches that in other embodiments, catalyst may be added in a solid state form (e.g., as an auger feed) [0109].
Considering Mubima’s disclosure in [0106-9], one having ordinary skill in the art would have recognized that in addition to ruthenium carbene complexes, both molybdenum and tungsten complexes were known in the art as suitable catalysts for cross metathesis of a natural oil feedstock and a short chain olefin. Case law has established that it is prima facie obvious to substitute one known element for another to obtain predictable results. KSR Int'l Co. v. Teleflex, Inc., 550 U.S. 398 (2007). MPEP 2143, rationale (B). It would have been obvious to the person having ordinary skill in the art, therefore, to have substituted the metathesis catalyst named by Behr (ruthenium carbene complex) for any other suitable metathesis catalyst known in the art, including a complex comprising molybdenum and/or tungsten, as disclosed by Mubima, in order to effectively perform the cross-metathesis reaction disclosed by Behr. Additionally, it would have been obvious to the person having ordinary skill in the art to have added the metathesis catalyst in a slurried or solid form, as taught by Mubima, in order to eliminate solvent from the process.
As to the recited reactions to convert 9-decenoic acid methyl ester to 10-aminodecanoic acid methyl ester (reaction with a brominating agent and then with an aminating agent):
As set forth in the discussion above, Behr discloses converting 9-decenoic acid methyl ester to 10-aminodecanoic acid methyl ester, but fails to teach the specific chemical reactions required to produce 10-aminodecanoic acid methyl ester from 9-decenoic acid methyl ester.
Annoot teaches a continuous process for producing a compound of the formula Br-(CH2)n-R2 by hydrobromination of an unsaturated reagent CH2=CH-R2 (where R2 may be hydrogen or an alkyl radical (including linear saturated, and may be functionalized) with a molar excess of HBr [0014-16, 19]. Annoot further teaches an ammonolysis (amination) step to form NH2-(CH2)n-R2, and a further step of synthesis of polyamide by polymerization of NH2-(CH2)n-R2 [0065]. Annoot teaches that the disclosed process is a continuous industrial process which makes it possible to control and optimize various parameters of the hydrobromination reaction, and makes it possible to achieve imposed specifications in terms of conversion and yield, and improves the quality of the product obtained [0012]. The disclosed process further achieves or exceeds the yield obtained with current processes, but avoids the use of aromatic and/or halogenated solvents for health/safety reasons [0009-10].
When converting a compound encompassed by Annoot’s general formula CH2=CH-R2 to an amine according to Annoot’s general formula NH2-(CH2)n-R2, the person having ordinary skill in the art would have been motivated to perform brominating and ammonolysis reactions, as disclosed by Annoot, in order to achieve the desired aminated product with improved yield, and without using dangerous or toxic solvents. It would have been obvious to the person having ordinary skill in the art, therefore, to have carried out the “follow-up chemistry” in the synthesis shown by Behr in figure 21 by reacting Behr’s methyl ester of 9-decenoic acid (a compound encompassed by Annoot’s formula CH2=CH-R2) with HBr as brominating agent (as taught by Annoot), and by subsequently reacting the resulting methyl ester of 10-bromodecanoic acid with ammonia (ammonolysis) as aminating agent (as disclosed by Annoot), in order to provide Behr’s desired intermediate product shown in figure 21: methyl ester of 10-aminodecanoic acid (i.e., a compound encompassed by Annoot’s formula NH2-(CH2)n-R2) safely, and with improved quality.
Response to Arguments
Applicant's arguments filed 11/3/2025 have been fully considered.
Applicant argues (p 5) that the cited references fail to teach unsaturated fatty acid esters which comprise a carbon-carbon double bond between the ninth and tenth carbon atoms from the ester group reacted with a triene having at least one double bond in the presence of a metathesis catalyst. However, each of these limitations is addressed with citation to a prior art reference in the rejection above.
Applicant further argues (pp 5-6) that Behr does not teach the use of unsaturated triene, nor the drawbacks of ethenolysis. This argument was previously addressed in paragraphs 25-26 of the 1/21/25 action.
Applicant argues (p 6) that Mubima does not disclose any reasons to use trienes in a reaction with unsaturated natural fatty acid esters, and therefore one would have no motivation to modify Behr with the teachings of Mubima. This argument was previously addressed in paragraph 26 of the 1/21/25 action.
Applicant further argues (pp 6-7) that the office has not demonstrated that the claimed method is one of a finite number of methods to synthesize polyamide-10, and, that Mubima and Behr are directed to different final products and therefore not combinable. These arguments were previously addressed in paragraphs 27-28 of the 1/21/25 action.
Conclusion
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 RACHEL KAHN whose telephone number is (571)270-7346. The examiner can normally be reached Monday to Friday, 8-5.
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/RACHEL KAHN/Primary Examiner, Art Unit 1766
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