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 in response to applicant’s communication filed on 11/25/25.
Claims 1-5 and 7-9 are pending in this application.
Applicant's election with traverse of Group 1, claims 1-7, in the reply filed on 11/25/25 is acknowledged. The traversal is on the ground(s) that the Office Action has not established that it would pose an undue burden to examine the full scope of the claims. This is not found persuasive because the claims of the various groups are divergent in subject matter and are classified separately. Thus claims 8-9 are withdrawn from consideration being drawn to the non-elected invention.
Applicant’s election of the following amine compound is acknowledged herewith:
N,N-dimethyl- 2-(2-(methylamino)ethoxy)ethan-1-amine
with the following structure:
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Thus, additionally, claim 5 is hereby withdrawn from consideration being non-readable on the elected species
As a result, claims 1-4 and 7 are being examined in this Office Action.
Priority
The applicant claims benefit as follows:
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Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
Claims 1-4 and 7 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112, second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention.
Claim 1 is indefinite because the structure of the amine product(s) is unclear. Applicant claims a method of producing a secondary amine or a tertiary amine product but provides no structure for the product being formed. This is especially confusing since the amine of formula (2) reactant can read on applicant’s secondary amine or a tertiary amine product. When any of R1, R2, R4 or R5 is an alkyl group for applicant’s amine of formula (2), then this amine reactant would read on applicant’s secondary amine product. Also when either (R1 and R2) or (R4 and R5) are alkyl groups for applicant’s amine of formula (2), then this amine reactant would read on applicant’s tertiary amine product.
Thus applicant’s claimed amine product can merely read on applicant’s reactant of formula (2). This would mean no reaction needs to take place, since applicant’s amine reactant would read on applicant’s amine product. The lack of specificity for the amine product and reaction mechanism in the claims could imply no active step.
Additionally, because claim 1 does not clearly set forth the structure of the product, nor the particular mechanism or synthetic reaction of the alcohol and amine reactants, it is unclear what method/process applicant is intending to encompass.
For the purposes of examination, the examiner interprets the claims as reading on a coupling reaction by the condensation of an amine and an alcohol reactant, which substitutes a hydrogen atom with an alkyl group to release water, to form a higher substituted amine product through nucleophilic substitution.
The dependent claims are rejected as being dependent on a rejected claim. Appropriate correction is required.
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 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 1-4 and 7 are rejected under 35 U.S.C. 103 as being unpatentable over Gaspar et al. (US 20120071622, pub date March 22, 2012).
Determination of the Scope and Content of the Prior Art
(MPEP §2141.01)
Gaspar et al. teaches the formation of a secondary or tertiary amine product by the reaction of ammonia with an alcohol to form a coupled amine product(s) by the use of a 2CuOxCr2O3 catalyst (which reads on applicant’s copper-chromite catalyst in claim 2).
See paragraphs 38-39, 71, 88, 116, 122-127, 131, Example 1, Tables 1 and 2.
As shown in the reaction below from paragraph 122, the alcohol reactant, 2-(2-(dimethylamino)ethoxy)ethan-I-ol (from applicant’s claim 3), reacts with ammonia, in a condensation reaction which releases water, to form a higher substituted amine products through nucleophilic substitution.
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The alcohol reactant from the scheme above is 2-(2-(dimethylamino)ethoxy)ethan-I-ol (also known as N,N-2-dimethylaminoethanoxyethanol), with the structure below.
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One of the amine products is (T2) from the reaction scheme above, has the structure and name below:
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Another of the amine products is (T3) from the reaction scheme above, which has the structure and name below:
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The (T3) amine product is applicant’s elected amine species: N,N-dimethyl- 2-(2-(methylamino)ethoxy)ethan-1-amine.
Another coupled product from the reaction scheme above is the amine product, bis(N,N-2-dimethylaminoethoxyethyl)amine with the structure below:
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Thus, it would be reasonable to expect that the bis coupled amine product, bis(N,N-2-dimethylaminoethoxyethyl)amine, as shown above, is formed by a condensation reaction of the alcohol reactant, 2-(2- (dimethylamino)ethoxy)ethan-I-ol (also known as N,N-2-dimethylaminoethanoxyethanol) with the amine (T2), which would release water, through nucleophilic substitution, since Gaspar et al. already teaches the reaction conditions are conducive to condensation reactions of amines and alcohols, and because the chemical structure of the bis coupled amine product, bis(N,N-2-dimethylaminoethoxyethyl)amine, contains the carbon backbone of the amine (T2) and the alcohol reactant, 2-(2- (dimethylamino)ethoxy)ethan-I-ol.
The condensation reaction in the scheme above forms not only bis(N,N-2-dimethylaminoethoxyethyl)amine with the structure below:
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,
but also the structurally similar bis coupled methylamine product, bis(N,N-2-dimethylaminoethoxyethyl)methylamine, with the structure below:
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Thus, it would be reasonable to expect that the bis coupled methylamine product with the structure directly above, bis(N,N-2-dimethylaminoethoxyethyl)methylamine, is formed by a condensation reaction of the alcohol reactant, 2-(2- (dimethylamino)ethoxy)ethan-I-ol (also known as N,N-2-dimethylaminoethanoxyethanol) with the amine (T3), which would release water, through nucleophilic substitution, since Gaspar et al. already teaches the reaction conditions are conducive to condensation reactions of amines and alcohols, and because the chemical structure of the bis coupled methylamine product, contains the carbon backbone of the amine (T3) and the alcohol reactant, 2-(2- (dimethylamino)ethoxy)ethan-I-ol.
Thus Gaspar et al. teaches the equivalency of the two bis coupled amine products, with the structures as shown below:
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and the equivalency of the two amine reactants (T2) and (T3), with the structures as shown below:
(T2)
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(T3)
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Gaspar et al. teaches the molar ratios of the reactants, ammonia to the alcohol range from 0.5 to 20. (paragraph 18)
Ascertainment of the Difference Between Scope the Prior Art and the Claims
(MPEP §2141.012)
Gaspar et al. is deficient in the sense that it does not exemplify the synthesis of the bis coupled amine product, bis(N,N-2-dimethylaminoethoxyethyl)methylamine, from the condensation reaction of the alcohol reactant, 2-(2- (dimethylamino)ethoxy)ethan-I-ol (also known as N,N-2-dimethylaminoethanoxyethanol) with the amine (T3).
Finding of Prima Facie Obviousness Rationale and Motivation
(MPEP §2142-2143)
However, it would be prima facie obvious to one of ordinary skill in the art at the time of the invention, to utilize the two reactants, the amine, N,N-dimethyl- 2-(2-(methylamino)ethoxy)ethan-1-amine (T3) (applicant’s elected species amine in claim 4) and the alcohol, 2-(2-(dimethylamino)ethoxy)ethan-I-ol, (from applicant’s claim 3), in a condensation reaction to form the bis coupled methylamine product, bis(N,N-2-dimethylaminoethoxyethyl)methylamine, since the bis coupled methylamine product was found in the reaction mixture of the two reactants, the amine and alcohol.
Since both the amine and alcohol reactant are components in the reaction solution, it would be reasonable to expect the amine and alcohol reactants to condense and release water to form the bis coupled methylamine product. One of ordinary skill in the art can trace the reactants that form the bis coupled methylamine product, bis(N,N-2-dimethylaminoethoxyethyl)methylamine, to come from the chemical backbone of the amine, N,N-dimethyl- 2-(2-(methylamino)ethoxy)ethan-1-amine (T3) and the alcohol, 2-(2- (dimethylamino)ethoxy)ethan-I-ol reactants. Typically in condensation reactions when multiple condensed and coupled products are formed, alcohol reactants condense with amine products formed in situ, to form higher substituted amine products, as shown by the formation of the the bis coupled methylamine product, bis(N,N-2-dimethylaminoethoxyethyl)methylamine.
With regard to applicant’s weight ratio of the alcohol to the amine in claim 7, it would be obvious to optimize the weight ratio of the reactants, which would include the alcohol and the amine, since Jaspar et al. teaches a wide range of molar ratios of the reactants. Thus it would be obvious to optimize the weight ratio of the reagents, since the ratio of alcohol and amine is considered a result-effective variable, absent evidence to the contrary.
Conclusion
No claim is allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jennifer Cho Sawyer whose telephone number is (571) 270 1690. The examiner can normally be reached on Monday-Friday 9 AM - 6 PM PST.
If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Renee Claytor can be reached on (571) 272-8394. The fax phone number for the organization where this application or proceeding is assigned is 571-274-1690.
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Jennifer Cho Sawyer
Patent Examiner
Art Unit: 1691
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691