DETAILED ACTION
The present application is being examined under the pre-AIA first to invent provisions.
Receipt and consideration of Applicant’s amended claim set and Applicant’s arguments/remarks submitted on September 25, 2025 are acknowledged.
All rejections/objections not explicitly maintained in the instant office action have been withdrawn per Applicant’s claim amendments and/or persuasive arguments. Applicant’s claim amendments have necessitated new grounds of rejections set forth below.
Status of the Claims
Claims 1-8, 10-19, 21, 22, and 25 are pending and under consideration in this action. Claims 9, 20, 23, and 24 are cancelled.
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on October 22, 2025 has been entered.
Terminal Disclaimer
The terminal disclaimer filed on September 25, 2025 disclaiming the terminal portion of any patent granted on this application which would extend beyond the expiration date of any patent granted on pending Application No. 14/857,507 has been reviewed and is accepted. The terminal disclaimer has been recorded.
Change in Examiner
The examiner for your application in the USPTO has changed. Examiner Monica Shin can be reached at 571-272-7138.
Claim Objections
Applicant is advised that should claim 11 be found allowable, claim 12 will be objected to under 37 CFR 1.75 as being a substantial duplicate thereof. When two claims in an application are duplicates or else are so close in content that they both cover the same thing, despite a slight difference in wording, it is proper after allowing one claim to object to the other as being a substantial duplicate of the allowed claim. See MPEP § 608.01(m). A triglyceride is either a fat or an oil, and thus claim 12 merely defines what a triglyceride is. Thus, claim 12 is identical in scope to claim 11.
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.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1, 4, and 11 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 1 recites the limitation “the adjuvant reacting product” in line 7. There is insufficient antecedent basis for this limitation in the claim because there is no previous introduction of “an adjuvant reacting product”. It is noted that line 3, for example, recites forming “an adjuvant reaction product”.
Claim 1 recites the limitation "the adjuvant product reaction" in line 16. There is insufficient antecedent basis for this limitation in the claim because there is no previous introduction of “an adjuvant product reaction”. It is noted that line 3, for example, recites forming “an adjuvant reaction product”.
Claim 4 recites the limitation "the amidoamine alkoxylate reaction product " in line 5. There is insufficient antecedent basis for this limitation in the claim because there is no previous introduction of “an amidoamine alkoxylate reaction product”. It is noted that line 3, for example, recites forming “an amidoamine alkoxylate”.
Claim 11 recites the limitation "the amidoamine alkoxylate reaction product " in lines 5-6. There is insufficient antecedent basis for this limitation in the claim because there is no previous introduction of “an amidoamine alkoxylate reaction product”. It is noted that line 3, for example, recites forming “an amidoamine alkoxylate”.
Claim Rejections - 35 USC § 103
The following is a quotation of pre-AIA 35 U.S.C. 103(a) which forms the basis for all obviousness rejections set forth in this Office action:
(a) A patent may not be obtained though the invention is not identically disclosed or described as set forth in section 102, if the differences between the subject matter sought to be patented and the prior art are such that the subject matter as a whole would have been obvious at the time the invention was made to a person having ordinary skill in the art to which said subject matter 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 pre-AIA 35 U.S.C. 103(a) 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 under pre-AIA 35 U.S.C. 103(a), the examiner presumes that the subject matter of the various claims was commonly owned at the time any inventions covered therein were made absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and invention dates of each claim that was not commonly owned at the time a later invention was made in order for the examiner to consider the applicability of pre-AIA 35 U.S.C. 103(c) and potential pre-AIA 35 U.S.C. 102(e), (f) or (g) prior art under pre-AIA 35 U.S.C. 103(a).
Claims 1-8, 10-19, 22, and 25 are rejected under pre-AIA 35 U.S.C. 103(a) as being unpatentable over Pallas (US20030087764, from IDS), Danner (US4572721; of record) as evidenced by Arbogast (US20090186767; of record), and Koshti (US7534816; of record).
With regards to Claims 1-8, 10-19, and 22, Pallas teaches agricultural compositions comprising pesticides which use amidoamines which are alkoxylated and which correspond to applicant’s formula, see Pallas formula 37, wherein applicant’s R1 is a hydrocarbyl having from 1-30 carbons; Pallas’ X is C(O)N(R9) wherein R9 is hydrogen and z is 1, which reads on the left-most amide in applicant’s formula; (R8)n is -CH2-CH2 (e.g. (CH2)c) wherein applicant’s c is 2; y is 0; R4 and R3 and R5 are (R6O)xR7 wherein R6 is C2-C4 alkylene and x is a whole number from 1-30, e.g. 3 (there is a typo in Pallas referring to this as y but it is clear from paragraph 114 in Pallas, that this is meant to be x) which reads on the instantly claimed wherein b is 2 and all of applicant’s claimed ranges of b, and R7 is H, a is 1, and R2 is CH2-CH2 (e.g. (CH2)c) wherein applicant’s c is 2, (see entire document; [0003]; [0069]; [0113-0114, formula (37), which also defines R6 to include CH2CH2 which reads on the instant formula/ethylene oxide)]; [0002]; [0043]; [0064]; etc.). Pallas teaches wherein these surfactants/adjuvants are useful for formulating storage stable pesticidal compositions, e.g. glyphosate, which are stable over broad temperature changes/shifts and exhibit enhanced glyphosate activity (See abstract; [0002]; [0030]; [0064]; [0113-0114)).
Pallas discloses that surfactants tending to give the most useful enhancement of glyphosate herbicidal effectiveness are generally but not exclusively cationic surfactants, including surfactants which form cations in aqueous solution or dispersion at pH levels of around 4-5 (para.0013).
With regards to Claims 1, 4, and 11, Pallas teaches wherein the glyphosate in their herbicidal compositions is/can be salts of glyphosate, specifically potassium glyphosate or ammonium glyphosate (See claims 1, 7-9; [0038]).
With regards to Claim 25, Pallas teaches wherein the agricultural composition has a pesticide concentration of from 150 gae/L to about 600 gae/L (claims 21-25; [0033-0034]; [0064]).
Pallas does not appear to explicitly disclose teach how to form the amidoamine adjuvants claimed, specifically wherein applicant’s a is other than 1, e.g. 2-3. Pallas also does not teach wherein the alkoxylation is done only with ethylene oxide. Danner and Koshti are relied upon for this disclosure. Their teachings are set forth herein below.
With regards to Claims 1, 4, and 11, Koshti teaches that it was known to react triglycerides or fatty acids with amines, specifically diamines, to form amidoamines (See Col. 5, ln. 18-21).
With regards to Claims 2-8, 10-19, and 22, Danner teaches forming amidoamine alkoxylates of the claimed formula via reacting a fatty acid, with an ethyleneamine, specifically diethylenetriamine which leads to compounds wherein a is 1, or triethylenetetramine which leads to compounds wherein a is 2 or tetraethylenepentamide which leads to compounds wherein a is 3 to produce an amidoamine intermediate product and then reacting the amidoamine with alkylene oxide, specifically ethylene oxide to form the claimed compounds (See entire document; Products A and B; Col. 1, ln. 31-Col. 2, ln. 58 inclusive; Col. 2, ln. 59-Col. 3, formula α, and ln 19-30), and Danner teaches wherein these compounds function as surfactants/surface active agents and can be combined with other surfactants, specifically ethoxylated fatty alcohols of formula VI (See Col. 5, ln. 35-42, ln. 49-53; Col. 6, ln.5-formula VI with definitions of R9 and g), and as is evidenced by Arbogast, these non-ionic surfactants of formula VI are pesticidal actives (see Arbogast abstract; [0021]; [0026-0027]; [0045]; [0046]).
Danner also discloses that the amines have hydrophilic properties to the extent that they are either water-soluble or at least self-dispersible in water at 20oC and pH ≤ 7, thus resulting in true solutions or giving a stable dispersion or a dispersion which can readily be re-dispersed by simple stirring after phase separation on storage (col.1, ln.30-43).
With regards to Claims 2, 4-5, 11, 18, and 19, Danner teaches wherein applicant’s b is from 3-30 which reads on the claimed 2-10 and 2-5 (See Col. 3, ln. 1-29).
With regards to Claim 22, Danner teaches wherein alkoxylation is done with only ethylene oxide (See col.7-8, Product A, Product B).
It would have been obvious to form the claimed alkoxylated amidoamines as taught by Pallas, Danner and Koshti using the methods of Danner because Pallas and Danner both teach that the claimed amidoamines alkoxylates are useful as surfactants and Pallas teaches that amidoamine alkoxylates are useful for formulating pesticides and Danner teaches forming effective formulations of the claimed amidoamine alkoxylates with pesticidal active agents, e.g. polyethoxylated fatty alcohols which are known pesticidal actives as evidenced by Arbogast (see abstract; [0021]; [0026-0027]; [0045]; [0046]), and Koshti teaches that triglycerides can be reacted with diamines to form amidoamines. One of ordinary skill in the art would have been motivated to combine the methods of Danner with the triglyceride starting material of Koshti in place of and/or in combination with the fatty acids of Danner and Pallas to form the claimed amidoamine alkoxylate compounds of Pallas and Danner when reacted with the ethyleneamines of Pallas which are instantly claimed, e.g. wherein a is 2 or 3 in order to provide an effective method to form these useful adjuvants for use in the pesticidal compositions of Pallas, especially since the compositions of Danner would also be pesticidal as they contain known pesticidal active agents as evidenced by Arbogast. Furthermore, the amine surfactants formed by Danner’s method help to provide solutions and dispersions that are stable during storage.
It also would have been obvious to form the claimed amidoamine alkoxylates as taught by the combined references and to use them to form the formulations of Pallas with glyphosate because the amidoamine alkoxylates claimed as taught by Danner are homologous to the amidoamine alkoxylate of Pallas which contains applicant’s a =1 and it is known, “Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). Thus, because the compounds of Danner teach that compounds wherein applicant’s a is 1, 2, or 3 as claimed all lead to surfactant compounds, it would have been obvious to one of ordinary skill in the art to use these surfactants in the compositions of Pallas in order to form the claimed pesticidal compositions because the amidoamine alkoxylates of Danner are homologous and differ only in the successive addition of the same chemical group e.g. applicant’s “a” and as such would be expected to possess similar properties as the claimed amidoamine alkoxylate in Pallas wherein applicant’s a =1 which is known to be useful for formulating the same/very similar glyphosate compositions as are instantly claimed which have the same glyphosate loading, etc. as is instantly claimed.
It also would have been obvious to react triglycerides with or in place of fatty acids with the ethyleneamines claimed as taught by Danner and Koshti to form the claimed amido amine alkoxylates because Danner teaches the claimed method of making amidoamine alkoxylates and the fatty acids of Danner can be substituted for triglycerides because Koshti teaches that triglycerides can be reacted with diamines, etc. to form amido amines thus one of ordinary skill in the art would obviously realize that the fatty acids of Danner could be substituted with triglycerides and/or combined with triglycerides and when reacted with the ethyleneamines claimed as are taught by Danner would result in the claimed compounds as long as at least 3 moles of the ethyleneamine (e.g. diethylenetriamine) are used for every 1 mole of triglyceride because the triglycerides clearly contain 3 fatty ester moieties for reaction with the ethyleneamines, thus for complete aminolysis of the triglycerides one of ordinary skill in the art would know that you would need at least 3 moles of the desired ethyleneamine for every 1 mole of triglyceride.
Regarding Claims 15-16, it would be obvious to use a molar ratio of triglyceride to alkyleneamine is about 1:3, and/or is greater than 1:3, favoring the alkyleneamine because the triglyceride contains 3 fatty esters per molecule of glycerin/glycerol and as such to fully react the triglyceride, one of ordinary skill in the art would recognize that at least 3 moles of alkyleneamine would need to be reacted with every 1 mole of triglyceride in order to afford full aminolysis of the triglycerides to form 3 moles of fatty amidoamine for every 1 mole of triglyceride.
Therefore, the claimed invention, as a whole, would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the instant invention, because the combined teachings of the prior art references is fairly suggestive of the claimed invention.
Claim 21 is rejected under pre-AIA 35 U.S.C. 103(a) as being unpatentable over Pallas (US20030087764, from IDS), Danner (US4572721; of record) as evidenced by Arbogast (US20090186767; of record) and Koshti (US7534816; of record) as applied to Claims 1-8, 10-19, 22, and 25 set forth above, further in view of Bigorra (EP0875500; of record).
The teachings of Pallas, Danner (evidenced by Arbogast), and Koshti, and the motivation for their combination as they apply to Claims 1-8, 10-19, 22, and 25 are set forth above and incorporated herein.
The combined teachings of Pallas, Danner, and Koshti do not appear to explicitly disclose where at least one of N’ or N” is quaternized. Bigorra is relied upon for this disclosure. The teachings of Bigorra are set forth herein below.
Bigorra teaches that by quaternizing similar amines leads to surfactants which are easier on skin, biodegradable, etc. (See Claims; Industrial applicability section; See paragraph beginning with, “Surprisingly, it has been found that the quaternized fatty acid amidoamine ethoxylates…”).
One of ordinary skill in the art would have found it prima facie obvious at the time the instant invention was made to further combine the teachings of Pallas, Danner, and Koshti, with the teachings of Bigorra, and quaternize the amidoamine alkoxylate surfactant of the combined teachings of Pallas, Danner, and Koshti discussed above. One of ordinary skill in the art would have been motivated to do so as it would allow to surfactant to incur benefits such as being biodegradable, thus being more environmentally friendly when applied. One of ordinary skill in the art would have had a reasonable expectation of success in doing so as Bigorra discloses that it is known to quaternize amines similar to that of the combined teachings of Pallas, Danner, and Koshti used as surfactants.
Therefore, the claimed invention, as a whole, would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the instant invention, because the combined teachings of the prior art references is fairly suggestive of the claimed invention.
Response to Arguments
Applicant's arguments filed September 25, 2025 have been fully considered but they are not persuasive.
(1) Applicant argues that a skilled person would not look to the cited combination of listed disclosures from different disciplines to form an amidoamine alkoxylate reaction product by reacting a triglyceride with an alkylene amine to product an amidoamine, alkoxylating the amidoamine with an alkylene oxide to form the amidoamine alkoxylate reaction product, and then combining the amidoamine alkoxylate reaction product wit ha glyphosate salt, a glufosinate salt, or combinations thereof.
With regards to Applicant’s argument (1), the traversal argument is not found persuasive. Analogous art may be from the same field of endeavor or reasonably pertinent to problem to be solved. In this case Danner is reasonably pertinent to the problem to be solved, specifically the synthesis of the amidoalkylalkoxylate surfactants as is instantly claimed and is also discussed above. Koshti is also reasonably pertinent to the problem to be solved. Koshti teaches forming amidoamines and quaternizing alkyl amidoamines and teaches that it was known to react triglycerides and/or fatty acids with amines, specifically diamines to form amidoamines because Koshti’s compounds are amidoamines, the amines have just be quaternized (See Col. 5, In. 18-21). Thus, Koshti itself is also directed to solving one of the same problems as Danner and Pallas and which is one of the problems of the instant claims, specifically forming amidoamine containing surfactants and utilizing these surfactants/adjuvants for various purposes. Thus, the combination of the prior art references is appropriate as they are reasonably pertinent to the same problem of making amidoamine and/or amidoamine alkoxylate surfactants which is what applicants active method steps are actually directed to.
(2) Applicant argues that the claimed amidoamine alkylate (the adjuvant) is a reaction product, not a homogeneous material. The described reaction starting materials and conditions lead to at least a mixture of materials including the amidoamine alkoxylates. Because chemical processes are not predictable, it is surprising and unexpected that the reaction products described in the present specification provided the claimed agricultural plant composition when the reaction conditions set out in the specification are used.
With regards to Applicant’s argument (2), the traversal argument is not found persuasive. In the rejection set forth above, Danner and Kashti were relied upon for the reaction steps. With regards to Applicant’s argument that it is surprising and unexpected that the reaction products described in the present specification provided the claimed agricultural plant composition when the reaction conditions set out in the specification are used, the traversal argument is not found persuasive because the claims as currently written do not appear to recite reaction conditions. The instant claims only recite the reaction components, which are disclosed by, for example Danner and Koshti, and discussed above in detail. Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993).
(3) Applicant argues that the rejection does not teach or suggest the recited amidoamine alkoxylate reaction product described in the present application would provide a capable agricultural plant composition. Applicant argues that the rejection does not provide a basis that shows a reaction product of amidoamine alkoxylates combined with a glyphosate salt or glufosinate salt is an obvious agricultural plant composition, and the office action has not shown that an amidoamine alkoxylate reaction product having at least some mixture of components (compared to a particular known and available amidoamine alkoxylate) will predictably provide a desired glyphosate or glufosinate herbicide.
With regards to Applicant’s argument (3), the traversal argument is not found persuasive. Pallas discloses that amidoamine alkoxylates are known to be combined with glyphosate salts. Furthermore, Pallas discloses that surfactants tending to give the most useful enhancement of glyphosate herbicidal effectiveness are generally but not exclusively cationic surfactants, including surfactants which form cations in aqueous solution or dispersion at pH levels of around 4-5 (para.0013). Danner and Koshti are relied upon for the disclosure of forming amidoamine alkoxylates that have surfactant properties. Danner discloses that the formed amines have surface-active properties and have hydrophilic properties to the extent that they are either water-soluble or at least self-dispersible in water at 20oC and pH ≤ 7, thus resulting in true solutions or giving a stable dispersion or a dispersion which can readily be re-dispersed by simple stirring after phase separation on storage (col.1, ln.30-43). Thus, the amidoamine alkoxylate surfactant formed by the reaction of the combined teachings of Danner and Koshti have the properties required by Pallas for use with glyphosate salts.
Conclusion
Claims 1-8, 10-19, 21, 22, and 25 are rejected. No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MONICA A. SHIN whose telephone number is (571)272-7138. The examiner can normally be reached Monday-Friday (9:00AM-5:00PM EST).
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/MONICA A SHIN/Primary Examiner, Art Unit 1616
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