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
This Office action is responsive to Applicant's Response to Election/Restriction, filed Sept. 13, 2023. As filed Claims 1-10 are pending.
Priority
This application filed 09/13/2023 is a National Stage entry of PCT/US2022/034131 , International Filing Date: 06/20/2022 PCT/US2022/034131 Claims Priority from Provisional Application 63215564 , filed 06/28/2021
Information Disclosure Statement
Applicants' information disclosure statements (IDS) have been considered except where lined through. Please refer to Applicants' copy of the 1449 submitted herein.
Claim Rejections - 35 USC § 112 – Scope of Enablement
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 1-10 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, because the specification, while being enabling for producing a monoalkyl ether by contacting an aluminosilicate or zeolite catalyst with an olefin and an alcohol selected from the following:
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And
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Wherein
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does not reasonably provide enablement for producing any ether by contacting any metallosilicate catalyst with any olefin and any alcohol.
The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make the invention commensurate in scope with these claims. This is a scope of enablement rejection.
The claim(s) contains subject matter which was not described in the specification in such a way as to enable one skilled in the art to which it pertains, or with which it is most nearly connected, to make and/or use the invention.
To be enabling, the specification of the patent must teach those skilled in the art how to make and use the full scope of the claimed invention without undue experimentation. In re Wright, 999 F.2d 1557, 1561 (Fed. Cir.1993). Explaining what is meant by "undue experimentation," the Federal Circuit has stated:
The test is not merely quantitative, since a considerable amount of experimentation is permissible, if it is merely routine, or if the specification in question provides a reasonable amount of guidance with respect to the direction in which the experimentation should proceed to enable the determination of how to practice a desired embodiment of the claimed invention. PPG v. Guardian, 75 F.3d 1558, 1564 (Fed. Cir. 1996).1
The factors that may be considered in determining whether a disclosure would require undue experimentation are set forth by In re Wands, 8 USPQ2d 1400 (CAFC 1988) at 1404 where the court set forth the eight factors to consider when assessing if a disclosure would have required undue experimentation. Citing Ex parte Formal, 230 USPQ 546 (BdApls 1986) at 547 the court recited eight factors:
1) nature of the invention,
2) state of the prior art,
3) relative skill of those in the art,
4) level of predictability in the art,
5) existence of working examples,
6) breadth of claims,
7) amount of direction or guidance by the inventor, and
8) quantity of experimentation needed to make or use the invention.
These factors are always applied against the background understanding that scope of enablement varies inversely with the degree of unpredictability involved. In re Fisher, 57 CCPA 1099, 1108, 427 F.2d 833, 839, 166 USPQ 18, 24 (1970). Keeping that in mind, the Wands factors are relevant to the instant fact situation for the following reasons:
State of the prior art and level of predictability in the art: The prior art bythe US 5,741,948 by Kirishiki et al. which discloses a process for the production of (poly) alkylene glycol monoalkyl ethers comprising reacting an olefin with a (poly) alkylene glycol in the presence of zeolite as catalyst (abstract and column 1, lines 61-65). The olefin used in the invention includes hydrocarbons of 2-40 carbon atoms (column 1, line 66 to column 2, line 10). The polyalkylene glycol used in the invention includes monoethylene glycol, diethylene glycol, etc. (column 2, lines 27-34). The reaction between the olefin and the (poly) alkylene glycol can be conducted in the presence of a solvent (column 3, lines 51-53. The reaction rate between the olefin and (poly) alkylene glycol is high and a (poly) alkylene glycol monoalkyl ether can be produced at a high conversion at a high selectivity.
Accordingly, the lack of significant guidance from the prior art with regard to reacting any olefin and any alcohol over any metallosilicate catalyst in aromatic solvent makes practicing the scope of the invention unpredictable.
The amount of direction or guidance provided and absence of working examples
Claim 1 is drawn to the generic alcohol and generic olefin as starting materials, the product of the method is not recited in the claims, whereas the instant specification describes and exemplifies only specific alcohols that obtain monoalkyl ether ([0045] and Examples on [0047]-[0061]).
Accordingly, the amount of direction presented and the number of working examples presented in the instant specification are narrow compared to the wide breadth of the claims at issue.
The quantity of experimentation necessary
Because of the known unpredictability of the art, and in the absence of experimental evidence, the instantly claimed method of contacting the metallosilicate catalyst with an olefin and an alcohol in solvent of formula I‒ could not be predicted as inferred by the claim and contemplated by the specification. MPEP 2164.01(a) states, "A conclusion of lack enablement means that, based on the evidence regarding each of the above factors, the specification, at the time the application was filed, would not have taught one skilled in the art how to make/or use the full scope of the claimed invention without undue experimentation. In re Wright, 999 F.2d 1557, 1562, 27 USPQ2d 1510, 1513 (Fed. Cir. 1993." That conclusion is clearly justified here.
Accordingly, the instant claim does not comply with the enablement requirement of § 112, since to practice the invention claimed in the patent a person of ordinary skill in the art would have to engage in undue experimentation, with no assurance of success.
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 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 of this title, 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.
Claims 1-10 are rejected under 35 U.S.C. 103 as being unpatentable over US 5,741,948 Apr. 21, 1998, by Kirishiki (hereinafter “ ‘the 948 patent” cited by Applicants in IDS) and further in view of Giani et al. Computers and Chemical Engineering 29 (2005) 1661–1676 (cited in PTO-892 attached herewith).
Instant claims are drawn to a method, comprising the step:
contacting an olefin, an alcohol, a metallosilicate catalyst and a solvent, wherein the solvent comprises structure (I):
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.
The ‘948 patent teaches a process for producing a (poly)alkylene glycol monoalkyl ether, by reacting in a liquid phase process an olefin comprising 2-40 carbon atoms , e.g. alpha olefins, 1-dodecene with a (poly)alkylene glycol, e.g. monoethylene glycol in the presence of the admixture of the crystalline metallosilicate molecular sieve catalyst, such as BEA aluminosilicate type zeolite and metal to yield the (poly)alkylene glycol monoalkyl ether in high conversion at a high selectivity; the olefin includes hydrocarbons of 2-40 carbon atoms; the alcohol includes monoethylene glycol, diethylene glyco (instant claims 1-4; col 1-2, claims 1,2, 7 of the cited reference; examples).
Regarding instant claim 5, the ‘948 patent teaches that the catalyst is a metallosilicate such as BEA aluminosilicate type zeolite crystalline which contains at least one metal element selected from the group consisting of Al, Fe, Ga and B. teaches the silicon -to-metal atomic ratio of 5-1500; and specifically teach silicon -to-metal atomic ratio of 10 for catalyst (4) (example 4 col 7-8, Table 4); and Si-to-Ga atomic ratio of 10 for the catalyst (5) (col 9).The crystalline metallosilicate used in the invention is crystalline aluminosilicate (col 2, lines 40-59). Specific examples of the crystalline metallosilicate used in the invention is disclosed in col 2, lines 50-65). The crystalline metallosilicate has a silica to metal (alumina) ratio of 5 to 1500, particularly 10 to 500 (col 2, line 66 to col 3, line 2).
Regarding instant claims 6 and 7, the prior art teaches the amount of solvent is used from 33 wt% to 72 wt% of the combined olefin, alcohol, and solvent (Examples 43-45). The molar ratio of olefin to (poly) alkylene glycol is not particularly restricted but is 0.05-20, preferably 0.1-10 (column 3, lines 60-62).
Regarding instant claims 8-10, the cited prior art teaches that the reaction between the olefin and the alcohol can be conducted in the presence of a solvent (column 3, lines 51-53). Suitable solvents include nitromethane, nitroethane, nitrobenzene, dioxane, ethylene glycol dimethyl ether (diglyme), sulfolane, benzene, toluene, xylene, hexane, cyclohexane, decane, paraffin, etc. (col 3, lines 53-56). The reaction rate between the olefin and (poly) alkylene glycol is high and a (poly) alkylene glycol monoalkyl ether can be produced at a high conversion at a high selectivity (column 4, lines 47-53).
The method of the present application differs from the method described in the ‘948 patent in that prior art does not disclose the use of a solvent having the claimed structure (I) for the formation of the same compound.
Regarding the limitation of instant claims about the solvent of formula I, choosing an appropriate solvent for the reaction is routine in chemical art. The use of common organic solvents, such as alcohol (e.g. methanol, ethanol, butanol) are the known options within the technical grasp of one of ordinary skill in the art.
As discussed in the article by Gani selection of appropriate solvents for the promotion of organic reactions, by using a rules-based procedure where the estimated reaction-solvent properties and the solvent-environmental properties guide the decision-making process is known in the art. Based on the teaching of prior art combined with technical knowledge, one or ordinary skills in the art would opt for appropriate solvent for the reaction, with reasonable expectation of success.
Furthermore, it is noted the ‘948 patent does not place any limits on the solvents suitable for the process, which implies that any known solvent or mixture thereof may be used in their process. The selection of a known material based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention, to utilize any known solvent or mixture thereof in the process of the ‘948 patent including the known solvents as clamed.
The rationale to support a conclusion that the claim would have been obvious is that teaching, suggestion, or motivation in the prior art that would have led one of ordinary skill to modify the prior art reference or to combine prior art reference teachings to arrive at the claimed invention. KSR, 550 U.S. at_, 82 USPQ2d at 1395.
Thus, the claimed invention as a whole is prima facie obvious over the combined teachings of the prior art.
Thus, the claimed invention as a whole is prima facie obvious over the combined teachings of the prior art.
Conclusion
Claims 1-10 are rejected.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ANA MURESAN whose telephone number is (571)-270-7587. The examiner can normally be reached on Monday through Friday, 8:30 am to 5:30 pm EST.
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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/ANA Z MURESAN/Primary Examiner, Art Unit 1692
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