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 .
This communication is responsive to the claim set and response to Restriction filed 05/29/2026. Claims 1-23 are currently pending. Elected Claims 1-21 are under consideration in this Office Action. Claims 22-23 are withdrawn.
Claims 1-21 are rejected for the reasons set forth below.
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.
Drawings
The drawings are objected to as failing to comply with 37 CFR 1.84(p)(5) because they include the following reference character(s) not mentioned in the description: numbers on the figures, for example, 1612, 1570 and 13 on FIG. 1; 807.4 and 246 on FIG. 2; 811.7, 247 and 13 on FIG. 3. Amendments to the specification to add the reference character(s) in the description in compliance with 37 CFR 1.121(b) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance.
Specification
The abstract of the disclosure is objected to because lines 1-2: “an amine compound amine compound containing” should read --an amine compound containing--. A corrected abstract of the disclosure is required and must be presented on a separate sheet, apart from any other text. See MPEP § 608.01(b).
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.
Claims 1-2, 4-6, 8-12 and 14-19 are rejected under 35 U.S.C. 103 as being unpatentable over Kothandaraman et al. (J. Am. Chem, Soc. 2017, 139, 2549-2552).
Regarding Claims 1-2, Kothandaraman teaches a process of catalytic dehydrogenative coupling of methanol and 1,2-diamine (ab.) wherein the catalysts are Ru pincer catalysts (Scheme 3 and P2551 left column middle). Attention is drawn to Scheme 3B (p2550), wherein xylylenediamines coupling of methanol in the present of pincer catalyst and in solvent produces polymeric urea and hydrogen (p2550, left column, the 2nd paragraph from the bottom). Kothandaraman further teaches a base additive, such as K3PO4, enhances catalytic activity. Thus, it would have been obvious to one ordinary skilled artisan before the effective filling date of the instant application to incorporate a base additive to the reactions of xylylenediamines coupling with methanol to enhance the reactions.
The xylylenediamines have the structuresof
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read on the instant formula (I) e.
The catalyst for the reactions of Scheme 3B is
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(p2550 right column top), which has the same structure of the instant complex 2 (see p17 of the instant US application publication).
Regarding Claims 4-5, the amine compounds of Kothandaraman are the amine compounds of the instant examples 14-15. Wherein m=n=1, comprising no heteroatoms.
Regarding Claims 6 and 8, Kothandaraman teaches the suitable amines are xylylenediamines
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(Scheme 3B p2550), wherein R1 and R2 are H.
Regarding Claims 9-11, as discussed above, the pincer catalyst used in scheme 3B is the instant complex 2. Additionally, Kothandaraman discloses that the suitable catalysts include (p2552 right column middle):
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which is the instant complex 1.
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which is the instant complex 5.
Regarding Claim 12, the scheme 3B reaction used 2 mmol methanol and 1 mmol amine compound.
Regarding Claim 14, Kothandaraman discloses base additive is used at 5 to 25 mol % of a reaction (Table 1) wherein one reaction has 1 mmol of an amine compound and 1 mmol of methanol (id.), therefore, the base additive is from 0.1 mmol to 0.5 mmol. Kothandaraman further discloses catalyst being used at 10 µmol (Scheme 3). Therefore, Kothandaraman discloses the base is present in molar excess of the metal pincer catalyst.
Regarding Claims 15-17, the reaction is processed in toluene at 1400C (Scheme 3B).
Regarding Claim 18, Kothandaraman discloses the polyurea is crushed out as white solids which are insoluble in water and most organic solvent (p2550, left column, the 2nd paragraph from the bottom). Therefore, it would be obvious for one ordinary skilled artisan to isolate the polyurea solids from the reaction system.
Regarding Claim 19, Kothandaraman discloses the purpose of the study is to provide renewable energy sources (p2649 right column, 1st paragraph), therefore, one ordinary skilled artisan would be motivated to use renewable reagent.
Claim 3 is rejected under 35 U.S.C. 103 as being unpatentable over Kothandaraman, as applied to Claim 1 above, and in further view of Milstein et al. (US2019/0366316 A1).
The disclosure of Kothandaraman on the instant Claim 1 is incorporated herein by reference.
Kothandaraman teaches dehydrogenative coupling of methanol with Ru pincer catalysts (see discussion of Claim 1). Kothandaraman is silent on the catalyst being a manganese-based complex.
However, Milstein teaches that manganese-based pincer catalysts can be used in dehydrogenative coupling of an alcohol and amine (ab.). Milstein further teaches that dehydrogenative of benzyl alcohol and benzylamine did not result in side products as seen in case of ruthenium catalysts ([0521]). In view of such benefit, one ordinary skilled artisan would have been motivated, before the effective filing date of the instant application, to replace the ruthenium catalysts with the manganese catalysts taught by Milstein for the process of Kothandaraman for reducing production of side products.
Claim 13 is rejected under 35 U.S.C. 103 as being unpatentable over Kothandaraman, as applied to Claim 1 above, and in further view of Milstein2017 et al. (US2017/0283447 A1).
The disclosure of Kothandaraman on the instant Claim 1 is incorporated herein by reference.
Kothandaraman discloses that a base additive enhances the activity of the Ru pincer catalysts but is silent on the base additive is one of the claimed compounds.
However, Milstein2017 teaches Ru pincer catalysts for dehydrogenation reactions (ab, Fig. 1 and Fig. 2). Milstein2017 further teaches that the reaction optionally includes one or more base additives for Ru pincer catalysts include compounds, such as sodium hydroxide, sodium hydride, potassium hydroxide, potassium hydride, etc. ([0043]). In view of such teaching, it would have been obvious to one ordinary skilled artisan to use one of the compounds taught by Milstein2017 for the process of Kothandaraman because Milstein teaches the compounds are suitable base additives for Ru pincer catalysts.
Claim 21 is rejected under 35 U.S.C. 103 as being unpatentable over Kothandaraman, as applied to Claim 1 above, and in further view of Wolf (J of Labelled Compounds and Radiopharmaceuticals, vol 59: 2, 38-47, 2016).
The disclosure of Kothandaraman on the instant Claim 1 is incorporated herein by reference.
Kothandaraman discloses a process of making polyurea from methanol and diamines but is silent on methanol being labelled.
However, Wolf discloses radiolabeled compounds are invaluable tools used to study synthetic processes and physical properties (Ab.). In view of such benefits, one ordinary skilled artisan would have been motivated to label the reactants for studying the synthesis process or physical properties of polyurea. And one ordinary skilled artisan would have been motivated to label methanol because one urea group has only one O atom, the resulted signal would be more accurate with methanol labelling than diamine labelling.
Claims 1-2, 4-13 and 15-20 are rejected under 35 U.S.C. 103 as being unpatentable over Kim et al. (Org. Lett., 2016, 18, 212–215) in view of Bulluck (US2009/0324974 A1), and in further view of Milstein2017 et al. (US2017/0283447 A1).
Regarding Claims 1 and 13, Kim teaches a process of dehydrogenative coupling of an amine compound and methanol in the presence of a Ru pincer catalyst to produce urea and hydrogen (P212, Scheme 1), wherein the Ru pincer catalyst is the metal pincer catalyst of the instant complex 2.
The difference between Kim and the instant claim 1 is that Kim is silent on the amine compound having the structure of the claimed formula (I).
However, Bulluck teaches a polyurea coating is formed by mixing one or more diisocyanates and one or more diamines ([0016], [0019], Example 1, claim 1) wherein the diamines are selected from cis-1,4-diaminocyclohexane; isophoronediamine; m-xylylenediamine; 4,4'-methylenedicyclohexylamine; menthanediamine; 1,4-diaminomethyl cyclohexane (claim 6). The aforementioned compounds read on the instant formula (I) (c ), (d), ( e).
One ordinary skilled artisan would have been motivated, before the effective filing date of the instant application, to adopt the diamines taught by Bulluck for the process of Kim to synthesize polyurea with the diamines and methanol in the presence of a Ru pincer catalyst because Kim teaches the process of synthesis of urea from amines and isocyanates causes tremendous toxicological
and environmental problems while the process of Kim using abundant and eco-friendly carbon source and no toxic byproduct (P212 right column) and Bulluck teaches polyureas are useful in caulks, adhesives, sealants, coatings, foams, and many other applications ([0011]). The combination of Kim and Bulluck would provide an eco-friendly process for synthesis of polyurea which would be useful in multiple applications.
The process of Kim in view Bulluck is silent on a base being involved in the reaction.
However, Milstein2017 teaches Ru pincer catalysts for dehydrogenation reactions (ab, Fig. 1 and Fig. 2). Milstein2017 further teaches that the reaction optionally includes one or more base additives for Ru pincer catalysts include compounds, such as sodium hydroxide, sodium hydride, potassium hydroxide, potassium hydride, etc. ([0043]). In view of such teaching, it would have been obvious to one ordinary skilled artisan to use one of the compounds taught by Milstein2017 for the process of Kim in view Bulluck because Milstein teaches the compounds are suitable base additives for Ru pincer catalysts.
Regarding claims 2 and 9-11, Kim teaches the preferred catalyst having the structure of:
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which is the same as the instant catalyst 2, wherein X=Y=H. Therefore, the catalyst reads the limitations of the instant Claims 2 and 9-11
Regarding Claims 4-6 and 8, m-xylylenediamine meets the limitations of the instant Claims 4-6 and 8.
Regarding Claim 7, menthanediamine has both of R1 and R2 being C1 hydrocarbyl groups. In addition, the diamine of Example 1 is Clearlink 1000 which has the structure of:
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. Which has both R1 and R2 being C4 hydrocarbyl groups.
Regarding Claim 12, the reaction d of Kim has methanol in molar excess of the amine compound (Scheme 2).
Regarding Claims 15-17, Kim shows the reaction is processed in toluene under 1400C (Scheme 2).
Regarding Claim 18, Kim discloses isolating yield (Scheme 2 and Scheme 3).
Regarding Claim 19, Kim teaches using renewable carbon resource (p212, 1st para.).
Regarding Claim 20, Kim teaches that one suitable diamine is cis-1,4-diaminocyclohexane which has the close structural similarities with 1,2-diarninocyclohexane. 1,2-diarninocyclohexane is a chiral diamine. Aa prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. "An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties." (MPEP 2144.09(I) Compounds that are homologs are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. (MPEP 2144.09(II) (In this instance, cis-1,4-diaminocyclohexane and 1,2-diarninocyclohexane only differ in the position of one amine group and they are both used for synthesis of polyurea. It would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have used 1,2-diarninocyclohexane for the process of Kim.
Claim 21 is rejected under 35 U.S.C. 103 as being unpatentable over Kim in view of Bulluck and in view of Milstein2017, as applied to Claim 1 above, and in further view of Wolf (J of Labelled Compounds and Radiopharmaceuticals, vol 59: 2, 38-47, 2016).
The disclosure of Kim in view of Bulluck and in further view of Milstein2017 on the instant Claim 1 is incorporated herein by reference.
Kim in view of Bulluck and in view of Milstein2017 discloses a process of making polyurea from methanol and diamines but is silent on methanol being labelled.
However, Wolf discloses radiolabeled compounds are invaluable tools used to study synthetic processes and physical properties. In view of such benefits, one ordinary skilled artisan would have been motivated to label the reactants for studying the synthesis process or physical properties of polyurea. And one ordinary skilled artisan would have been motivated to label methanol because one urea group has only one O atom, the resulted signal would be more accurate with methanol labelling than diamine labelling.
Conclusion
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/HUIHONG QIAO/ Examiner, Art Unit 1763 /JOSEPH S DEL SOLE/Supervisory Patent Examiner, Art Unit 1763
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