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 .
Election/Restrictions
Applicant’s election without traverse of the following species in the reply filed on 1/27/2026 is acknowledged:
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The election appears to read on claims 1-21, wherein the compound is a multiple charged cationic compound having 2 or more positive charges as defined by Y.
Claim Status
Claims 1-21 were filed on 5/12/2023 and are currently pending and under examination.
Priority
The application was filed on 5/12/2023 and claims the benefit of priority to:
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. See filing receipt dated 6/1/2023.
Specification/Drawings
The disclosure is objected to because of the following informalities.
The figures in the following paragraphs of the specification are objected to because they are blurry and contain greyscale which makes them difficult to read:
[0067] and [0217]-[0220].
Appropriate correction is required.
The drawings are objected to because the product in Fig. 2 is blurry and difficult to read.
Corrected drawing sheets in compliance with 37 CFR 1.121(d) 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. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. 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.
Claim Objections
Claims 1, 6, 11-13, 15, and 21 are objected to because of the following informalities:
In line 1 of claim 1, the words “Addition” and “Reaction” should not be capitalized.
In line 2 of the definition of variable R2’ in claim 1, the word “or” should be inserted before the limitation “alkynyl” to indicate that the “linear or branched C1-C10” limitation applies to the alkyl, alkenyl, and alkynyl group.
In line 1 of claim 6, the word “wherein” should be inserted after the phrase “claim 1,”.
Claims 11 and 12 are objected to because the figures are blurry and include greyscale which makes them hard to read.
In claims 11 and 12, the phrase “one or more” should be deleted from line 1 and replaced by –one of--.
In line 2 of claims 13 and 15, the limitation “(3-Acrylamidopropyl)” should not be capitalized.
In the final line of claim 21, the word “Gemini” should not be capitalized.
In the final line of claim 21, there appears to be a grammatical error. The phrase “Gemini, surfactant or mixtures thereof” should read “or gemini surfactant, or mixtures thereof”.
Appropriate correction is required.
Claim Rejections - 35 USC § 112(b)
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.
Claim 5 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 5 is rejected for being indefinite because the variable “n” is undefined. Therefore, the metes and bounds of the limitations are unknown.
Claim Interpretation
Independent claim 1 is a product-by-process claim. "[E]ven though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process." In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985) (citations omitted). See MPEP 2113.
Claim Rejections - 35 USC § 102
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.
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claim(s) 1, 3, 4, 6-9, and 16-20 is/are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Dhawan (US2019/0062187A1, published on 2/28/2019, claiming the benefit of priority to US provisional app. no. 62/552108, filed 8/30/2017) as evidenced by National Center for Biotechnology Information (2026). PubChem Compound Summary for CID 6435904, N-Oleyl-1,3-propanediamine. Retrieved March 2, 2026 from https://pubchem.ncbi.nlm.nih.gov/compound/N-Oleyl-1_3-propanediamine.
The applied reference has a common assignee with the instant application. Based upon the earlier effectively filed date of the reference, it constitutes prior art under 35 U.S.C. 102(a)(2). This rejection under 35 U.S.C. 102(a)(2) might be overcome by: (1) a showing under 37 CFR 1.130(a) that the subject matter disclosed in the reference was obtained directly or indirectly from the inventor or a joint inventor of this application and is thus not prior art in accordance with 35 U.S.C. 102(b)(2)(A); (2) a showing under 37 CFR 1.130(b) of a prior public disclosure under 35 U.S.C. 102(b)(2)(B) if the same invention is not being claimed; or (3) a statement pursuant to 35 U.S.C. 102(b)(2)(C) establishing that, not later than the effective filing date of the claimed invention, the subject matter disclosed in the reference and the claimed invention were either owned by the same person or subject to an obligation of assignment to the same person or subject to a joint research agreement.
Regarding claims 1 and 8, Dhawan teaches the following example in [0226]:
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A diamine, N-oleylpropanediamine, is reacted with (3-acrylamidopropyl) trimethylammonium chloride (APTAC-claim 6), an activated olefin of the first claimed formula wherein R2 is H; X is NH; R3 is -CH2-CH2- (C2 alkyl); and Y is NR4R5R6(+), wherein R4, R5, and R6 are methyl (C1 alkyl) to produce a single compound: 3,3’-((3,3’-((3-(octadec-9-en-1-yl-amino)propyl)azanediyl)bis(propanoyl)bis(azanediyl))bis(N,N,N-trimethylpropan-1-aminium chloride, which corresponds to an instantly claimed cationic compound comprising two positive charges. As evidenced by CID 6435904, N-oleylpropanediamine is a modified diamine (see p. 16 of the specification as filed and claim 3) with a primary amine group and a secondary amine group (option (i) in claim 4) and a molecular weight of 324.6 g/mol (daltons) (claims 7 and 9). Dhawan further teaches that the compound is soluble in water and an aqueous solution thereof (claims 16-20). Also see MPEP 2131.
Claim(s) 1-3, 5-9, and 16-20 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Yu (CN106750235A, published on 5/31/2017, including machine generated translation thereof) as evidenced by National Center for Biotechnology Information (2026). PubChem Compound Summary for CID 162071, Ethanaminium, N,N,N-trimethyl-2-[(1-oxo-2-propen-1-yl)oxy]-, chloride (1:1). Retrieved March 2, 2026 from https://pubchem.ncbi.nlm.nih.gov/compound/trimethyl_2-prop-2-enoyloxyethyl_azanium-chloride and Huntsman (“Epoxy Formulations Using Jeffamine® Polyetheramines”, p. 1-3, published 2005, downloaded from https://polymerinnovationblog.com/wp-content/uploads/2020/08/Huntsman-epoxy_formulations_using_jeffamine_polyetheramines.pdf on 3/2/2026).
Regarding claims 1 and 17, Yu teaches a method for preparing a quaternary ammonium salt type hydrophilic UV light curing resin. See abstract. Yu teaches that the process comprises reacting a binary polyether amine (diamine) with acryloyloxyethyltrimethylammonium chloride to give a double terminal secondary amino compound intermediate. See abstract and claims. This intermediate corresponds to the instantly claimed compound. Specific examples of the diamine are discussed in claim 3. As evidenced by CID 162071, the acryloyloxyethyltrimethylammonium chloride of Yu corresponds to a compound of the first activated olefin (Michael acceptor) claimed wherein R2 is H; X is O; R3 is -CH2-; and Y is -NR4R5R6(+), wherein R4, R5 and R6 are all methyl (C1 alkyl). Thus, the double terminal secondary amino compound intermediate produced in Yu corresponds to an instantly claimed single di-cationic compound having two positive charges. Also see examples 1-5 in Yu and MPEP 2113.
Further regarding the polyamine, as evidenced by Huntsman (p. 3), the polyamines D-230, D-400, and D-2000 (claim 3 of Yu) correspond to the instantly claimed polyamines wherein they are substituted polyamines (options (ii) or (iii) of claim 3, also see definition of “substituted” on p. 9 of the specification as filed) of formula NH2-[R10’]n-NH2, wherein R10’ is a substituted C3 alkyl group and n is 1-32 (see variable x on p. 3 of Huntsman) (claims 2 and 5), and having molecular weights of 230, 400, or 2000 Da respectively (claims 7 and 9). Further regarding claim 6, the activated olefin of Yu corresponds to the DMAEA-MCQ option (also see synonyms section of evidentiary CID 162071 reference). Further regarding claim 8, as the polyamine is a polymeric branched polymer, the product will comprise at least two multiple charged cationic compounds derived from the same polyamine and activated olefin. Also see MPEP 2131.
Regarding claim 16, Yu teaches that the process produces a hydrophilic UV curing resin comprising two water soluble quaternary amine groups. See abstract. As the intermediate compound of Yu, corresponding to the instantly claimed compound, possesses the water-soluble quaternary ammonium groups, the compound is presumed to be water soluble as well absent any evidence to the contrary. Also see the examples, wherein the activated olefin is added as an aqueous solution.
Regarding claims 18-20, the examples of Yu teach that the intermediate compound, corresponding to the instantly claimed compound, is formed in a mixture of water and ethanol, an alcohol. Also see MPEP 2131.
Claim(s) 1, 3, 6-9, 17 and 18 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Boday (US2016/0264734A1, published on 9/15/2016) as evidenced by National Center for Biotechnology Information (2026). PubChem Compound Summary for CID 69332, 4-Amino-N-methylaniline. Retrieved March 2, 2026 from https://pubchem.ncbi.nlm.nih.gov/compound/4-Amino-N-methylaniline) and CID 162071, Ethanaminium, N,N,N-trimethyl-2-[(1-oxo-2-propen-1-yl)oxy]-, chloride (1:1). Retrieved March 2, 2026 from https://pubchem.ncbi.nlm.nih.gov/compound/trimethyl_2-prop-2-enoyloxyethyl_azanium-chloride.
Regarding claims 1 and 8, Boday teaches the following example in [0022]:
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A diamine (4-(aminomethyl)aniline, an unmodified polyamine with a molecular weight of 122.17 g/mol (Da)-claims 3 and 7, also see evidentiary reference CID 69332) was reacted with [2-(acryloxyloxy)ethyl]trimethylammonium chloride (DMAEA-MCQ-claim 6) to provide the instantly claimed single cationic compound having two positive charges. DMAEA-MCG corresponds to a compound of the first activated olefin (Michael acceptor) claimed wherein R2 is H; X is O; R3 is -CH2-; and Y is -NR4R5R6(+), wherein R4, R5 and R6 are all methyl (C1 alkyl). As evidenced by CID 162071, the molecular weight of DMAEA-MCQ is 193.67 g/mol (Da). Thus, the molecular weight of the product is [(193.67*2) + (122.17) = 510 g/mol (Da), which falls within the range of claim 9. Also see MPEP 2131. Regarding claims 17 and 18, the product is contacted with NMP and formaldehyde (CH2O) and further reacted to form the final hexahydrotriazine product.
Claim(s) 1-10, 17, and 18 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Morinaga (WO2009/153209A1, published on 12/23/2009).
Regarding claim 1, Morinaga teaches the following example 3:
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A branched polyethyleneimine (BPEI, a polyamine) is reacted with [2-(acryloyloxy)ethyl]trimethylammonium chloride (DMAEA-MCQ-claim 6) to form BPEI having quaternary ammonium moieties (BPEI/QA). Also see discussion of the step on p. 4, 4th paragraph to p. 5, penultimate paragraph of Morinaga, wherein the activated olefin is a compound of formula (IV) of Morinaga. DMAEA-MCG corresponds to a compound of the first activated olefin (Michael acceptor) claimed wherein R2 is H; X is O; R3 is -CH2-; and Y is -NR4R5R6(+), wherein R4, R5 and R6 are all methyl (C1 alkyl). Morinaga teaches that the molecular weight of the BPEI is 1800 Da, thus molecular weight of the product should fall within the range of about 100 to about 2,000,000Da (claims 7 and 9). BPEI is a branched polyethyleneimine (option (iv) of claim 3) which includes primary and secondary amine groups (option (i) of claim 4) wherein the molar ratio of primary to secondary is 8.6 mmol : 8.2 mmol. See p. 3-4. The PEIs correspond to branched derivatives of formula H2N-(RN(R’))n-RNH2, wherein R is -CH2-CH2- and R’ is RNH2, RNHRNH2, or RN(RNH2)2, where n satisfies the MW of 1800 Da in the molar ratio of primary to secondary amine groups claims and is greater than 2 and less than 1,000,000 (claims 2 and 5). Further regarding claim 8, as the polyamine is a polymeric branched polymer (PEI), the product will comprise at least two multiple charged cationic compounds derived from the same polyamine and activated olefin. Regarding claim 10, the mass of the BPEI/QA product indicates that there are at least four positive charges (ie at least four amine moieties of BPEI undergo aza Michael reaction with the DMAEA-MCQ). Regarding claims 17 and 18, Morinaga teaches that octanol is added to the BPEI/QA product. Also see MPEP 2131.
Claim(s) 1-6, 8, 10, and 16-20 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Peng (“Synthesis and Application of Polyoxyethylene-Grafted Cationic Polyamidoamine Dendrimers as Retention Aids” Journal of Applied Polymer Science, 2007, p. 3468)
Peng teaches the following reaction:
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. See Scheme 1 on p. 3469. A polyamidoamine dendrimer with an ethylene diamine core (G5.0 PAMAM) was reacted with polyethoxyethylene (PEO) and acrylolyloxyethyl trimethylammonium chloride (DAC) to produce G5.0 PAMAM/DAC/PEO, a multiple charged cationic compound. Specific examples are provided in Table 1 on p. 3471:
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The polyamidoamine dendrimer (G5.0 PAMAM) corresponds to a substituted/modified branched polyamine of formula H2N-(RN(R’))n-RNH2, wherein R is substituted -CH2-CH2- and R’ is RNH2, RNHRNH2, or RN(RNH2)2, substituted by carbonyl groups (C=O) and having primary, secondary, and tertiary amine groups (claims 2-5). Also see last paragraph of col. 1 on p. 3471 regarding characterization of the amine groups. Acrylolyloxyethyl trimethylammonium chloride (DAC) is an activated olefin of the first structure in claim 1, wherein R2 is H; X is O, R3 is -CH2- and Y is -NR4R5R6(+), wherein R4, R5 and R6 are all methyl (C1 alkyl) or the DMAEA-MCQ of claim 6. Further regarding claims 8 and 10, the G5.0 PAMAM contains 128 primary amine groups and the ratio of DAC:PEO was varied according to Table 1. Therefore, the product exists as a mixture of at least two multiple charged cationic compounds derived for the same polyamine and activated olefin and has at least 4 positive charges. Regarding claims 16-20, the G5.0 PAMAM/DAC/PEO products are water soluble. See first full paragraph in col. 1 on p. 3472 to end of page. Additionally, the “synthesis” and “characterization” sections on p. 3469 teach solutions of the products in MeOH (an alcohol), D2O (NMR solvent), and CDCl3 (NMR solvent). Also see MPEP 2131.
Claim(s) 1, 3, 5, 7-10, and 16-20 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Schaper (US 4166894, published on 9/4/1979) as evidenced by the SciFinder entry for (US 4166894 (AN 1975:606793), obtained 3/5/2026).
Regarding claims 1 and 8, Schaper teaches the following example in col. 16:
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. As evidenced by AN 1975:606793, AMBTAC is a compound of the following structure:
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with a molecular weight of 234.77 g/mol (Da) (claim 7). Therefore, AMBTAC corresponds to an activated olefin of the first compound of claim 1, wherein R2 is H; X is NH; R3 is a branched C4 alkylene; and Y is NR4R5R6(+), wherein R4, R5, and R6 are methyl (C1 alkyl). Ethylene diamine is a compound of instant formula NH2-[R10’]n-NH2 in claim 5, wherein R10’ is a C2 alkylene and n is 1 (an unmodified polyamine-claim 3). As evidenced by AN 1975:606793, the molecular weight of the single indicated product of the Michael addition (TAMBTACEDA; corresponding to CAS reg. no. 57350-69-3) is 999.16 g/mol (Da-Claim 9) with four positive charges (claim 10). Regarding claims 16-20, the reaction solvent is water and the product does not precipitate out of the mixture, thus it is soluble in water. Also see MPEP 2131.
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 (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.
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.
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.
Claim(s) 1, 3, 5-12 and 16-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Schaper (US 4166894, published on 9/4/1979) as evidenced by the SciFinder entry for (US 4166894 (AN 1975:606793), obtained 3/5/2026).
Schaper is directed toward functional ionene compositions and their use. See abstract. Regarding claims 1, 8, 11, and 12, Schaper teaches that the preparation of the ionene compositions comprises a first step of functionalizing diamines, preferably by Michael addition with an acrylamide to produce a single functional diamine:
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. See col. 5, lines 32-67. The diamines prior to the Michael addition correspond to compounds of the following formula:
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. See col. 6, line 58-col. 7, line 5. The acrylamide Michael acceptors are of the following formula:
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, wherein R” can be one of the following quaternized groups
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(ester) or
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(amide). See col. 7, line 7-col. 8, line 2.
Schaper teaches exemplary acrylamides in the Table spanning col. 9-14, which include the following quaternized acrylamides:
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. See col. 11-12. These compounds correspond to Michael acceptors of the first formula of claim 1, wherein R2 is CH3; X is O or NH; R3 is a linear unsubstituted C1-2 alkylene; and Y is NR4R5R6(+), wherein R4, R5, and R6 are methyl (C1 alkyl). The Michael acceptors also correspond to the DMAEMA-MSQ (first compound above) and MAPTAC, (second compound above), of claim 6.
As previously discussed in the 35 USC 102 rejection above and incorporated herein, Schaper teaches anticipatory example 2 in col. 16, wherein AMBTAC, an activated olefin of the first compound of claim 1, wherein R2 is H; X is NH; R3 is a branched C4 alkylene; and Y is NR4R5R6(+), wherein R4, R5, and R6 are methyl (C1 alkyl) is reacted with ethylene diamine (an unmodified polyamine of claim 3) is a compound of instant formula NH2-[R10’]n-NH2 in claim 5, wherein R10’ is a C2 alkylene and n is 1 (an unmodified polyamine-claim 3) to produce the single compound TAMBTACEDA. Only one other diamine is exemplified, N,N’-dimethylenediamine (DMEDA). Ethylene diamine further corresponds to the polyamine core >N-CH2-CH2-N< of the compound of claim 11, wherein n is 0 and the first compound of claim 12.
Schaper does not explicitly teach embodiments wherein a diamine, in particular ethylene diamine (H2N-CH2-CH2-NH2) is reacted with methacrylamidopropyl trimethyl ammonium chloride (MAPTAC, the first exemplary (meth)acrylamides from the Table shown above) or the corresponding acrylamides (wherein R2 is H instead of CH3) to arrive at the compounds of claims 11 and 12, having four positive charges (claim 10).
It would have been prima facie obvious for one of ordinary skill in the art to arrive at embodiments of the instantly claimed invention wherein ethylene diamine is reacted acrylamidopropyl trimethyl ammonium chloride to arrive at the instantly claimed compounds of claims 11 and 12 based on the teachings of Schaper with a reasonable expectation of success before the effective filing date of the claimed invention. The skilled artisan would have been motivated to select ethylene diamine for the Michael reaction of Schaper because it falls within the broad genus of diamines, and is one of only two which are exemplified in the examples. The skilled artisan would have selected APTAC (a Michael acceptor of the first formula of claims 1 and 6, wherein R2 is H; X is NH; R3 is a linear unsubstituted C2 alkylene; and Y is NR4R5R6(+), wherein R4, R5, and R6 are methyl (C1 alkyl)) as the Michael acceptor for the Michael reaction of Schaper because Schaper exemplifies the methacrylic analog of said compound (R2 = CH3 instead of the claimed H, such that they are one-carbon homologs of one another) in the Table in col. 11-12, and also explicitly teaches an example wherein a branched homolog of said compound, APTAC, is reacted with ethylene diamine (example 2 in col. 16). The combined Micheal reaction between ethylene diamine and APTAC would predictably lead to compound of claim 11, wherein n is 0, which also corresponds to the first compound of claim 12. Reacting an exemplary diamine of Schaper with an exemplary acrylamide of Schaper, or their one carbon homologs, would be prima facie obvious and would predictably lead to the claimed compounds with a reasonable expectation of success. Further, due to the significant structural similarity between the claimed compounds and those exemplified in Schaper, the claimed compounds would also predictably be expected to possess similar properties and utilities as those described in Schaper. Also see MPEP 2144.08-09.
Further regarding claims 7 and 9, as discussed in the 35 USC 102 rejection over Schaper, both of the Michael acceptor and product had molecular weights falling within the claimed ranges. As the compound of claims 11 and 12 is a C2 homolog of that of example 2, then the molecular weights will be substantially the same (± C2H4, about 28). Likewise, regarding claims 16-20, the reaction solvent is water and the product of example 2 remains soluble in the water. Therefore, due to the significant structurally similarity between the compounds exemplified in Schaper and those of claims 11 and 12, the claimed compounds would also be presumed to be water soluble. Also see MPEP 2144.09.
Claim(s) 1-10 and 13-21 is/are rejected under 35 U.S.C. 103 as being unpatentable over Peng (“Synthesis and Application of Polyoxyethylene-Grafted Cationic Polyamidoamine Dendrimers as Retention Aids” Journal of Applied Polymer Science, 2007, p. 3468) in view of Manek (US 2006/0289359, published on 12/28/2006).
The teachings of Peng were discussed in the preceding rejection and incorporated by reference herein. Peng additionally teaches that polypropylene imine (PPI) dendrimers are also known to have the same utility as flocculants/retention aids as the G5.0 PAMAM/DAC/PEO products produced in Peng. See introduction section on p. 3468.
Peng does not explicitly teach embodiments of the claims wherein i) variable X in the activated olefin of claim 1 is NH (also corresponding to claims 13-15); ii) the use of polyethyleneimine (PEI) instead of PAMAM (claims 13-15); and iii) the addition of another surfactant to a composition comprising the inventive compound (claim 21).
Manek teaches a method of clarifying oily waste water comprising adding to the waste water an effective clarifying amount of one or more emulsifiers selected from the group consisting of dendritic polyamines, dendritic polyamidoamines (PAMAM) and hyperbranched polyethyleneimines (PEI) and the reaction products there of with gluconolactone, alkylene oxides, salts of 3-chloro-2-hydroxpropanesulfonic acid, alkyl halides, benzyl halides and dialkyl sulfates. See abstract. The molecular weight of the dendritic polyamine falls in the range of about 300 to 4000 Da, the molecular weight of the dendritic polyamidoamine (PAMAM) falls in the range of about 296 to about 4,000, and the molecular weight of the hyperbranched PEI falls in the range of about 800 to about 2,000,000 Da. See claims 3-8. The molecular weight of the PEI falls within the ranges in claim 7 and encompasses those of claims 13-15. Further regarding claim 9, the quaternization of the PEI will provide a product that falls within the claimed range. Also see MPEP 2144.05.
When the aforementioned polyamines or polyamidoamines of Manek are reacted with an alkylating agents (alkyl halides and benzyl halides), then terminal quaternized cationic amine compounds are produced. See claims 1-7 and [0026-0028]. When the polyamidoamine is used, the compound contains internal amide bonds (-NR-C(=O)), see claim 5, wherein R3 is -NCH2-CH2N(R4)2. This is consistent with the teachings of Peng regarding the structure of PAMAM. Manek teaches that these compounds act as demulsifiers/flocculants. See [0052]. Manek also teaches that other flocculants/demulsifiers are known and that the water clarification process disclosed is complex and requires several purification steps. See [0047-0060]. Therefore, Manek teaches cationic flocculants based on dendrimers and hyperbranched polyamines and polyamidoamines bearing multiple positively charged quaternized amine groups. These compounds are analogous to those in Peng.
It would have been prima facie obvious to combine the teachings of Peng and Manek to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to substitute variable X = O in the activated olefin of Peng to that of X = NH, because both Manek and Peng teach that amide functionalities can be tolerated in the dendrimer compounds. Therefore changing the linking group of the quaternary substituent (-N(Me3)(+)) in compounds of Peng from an ester -C(=O)-O- to -C(=O)-NH- to an amide would predictably lead to cationic compounds of Peng having the substantially the same, if not identical, flocculant properties. Also see MPEP 2143(I)(B) and MPEP 2144.09.
A person of ordinary skill would have been motivated to substitute the polyamine of Peng (PAMAM) for PEI because Manek teaches they are equivalent to one another in analogous cationic quaternary flocculants. Therefore, replacing one for another would predictably lead to cationic compounds of Peng having the substantially the same, if not identical, flocculant properties. Manek additionally teaches PEI having the same average molecular weight as those in claims 13-15. Also see MPEP 2144.05.
A person of ordinary skill would have been further motivated to arrive at the compounds of claims 13-15 because the claimed APTAC polyamine is one-carbon amide homolog of the ester DAC used in Peng. As discussed above, the combination of Peng and Manek provide motivation to replace the ester linkage of DAC with an amide linkage of APTAC. The skilled artisan would be further motivated to investigate homologs of the DAC because said homologs would predictably lead to cationic compounds of Peng having the substantially the same, if not identical, flocculant properties. Also see MPEP 2144.09. The claimed combination of elements to product the claimed compounds is known in the art as taught by Peng and Manek, and is shown to produce predictable results.
A person of ordinary skill would have been motivated to include another surfactant in the use of the inventive compounds of Peng because Manek teaches that the clarification process is complex and many require multiple steps and reagents. Manek further teaches that other surfactants are known in the art. Therefore, including another surfactant in the use composition of Peng would predictably produce another flocculation/demulsification composition suitable for its intended use. Also see MPEP 2144.06.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Clams 1-10 and 16-18 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 16-22, 25, and 101-111 of co-pending Application No. 18/304567 (‘567, reference application).
Although the claims at issue are not identical, they are not patentably distinct from each other because the compounds of formula (V) and (VIII) of the claims of ‘567 fall into the claimed genus wherein a modified polyamine (claim 3) comprising primary and tertiary amines (claim 4) is reacted with APTAC (claim 6, an activated olefin of the first claimed formula wherein R2 is H; X is NH; R3 is -CH2-CH2- (C2 alkyl); and Y is NR4R5R6(+), wherein R4, R5, and R6 are methyl (C1 alkyl)) to produce a multi-ionic cationic compound (claims 1 and 8). The bottom product can have at least 6 positive charges (claim 10). The polyamine of the second compound of claim 1 corresponds to a substituted PEI, which is a branched derivatives of formula H2N-(RN(R’))n-RNH2, wherein R is -CH2-CH2- and R’ is RNH2, RNHRNH2, or RN(RNH2)2 and variable n is >2 (claims 2 and 5). Regarding claims 7 and 9, see claim 18. Regarding claim 16, the ionic nature of the compound indicates that it will be water soluble. Regarding claims 17 and 18, the compound will be produced in a solvent. See claim 22.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Clams 1-21 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 21-24, 27-38, and 40 of co-pending Application No. 18/069681 (‘681, reference application).
Although the claims at issue are not identical, they are not patentably distinct from each other because they claim reacting an unmodified polyamine with a cationic monomer (Michael acceptor) of the first compound of instant claim 1, wherein instant R2, X, R3, and Y correspond to variables R1, X, M, and Z in the claims of ‘681 to produce a multiple charged cationic compound of claims 1 and 8. All of the activated olefins of claim 37 of ‘681 are recited in claim 6 and the compound of claim 24 and 38 is a species of the claimed compounds of claims 1, 11, and 12, wherein n is 1 to 100. The compound of claim 24 is derived from the reaction between an unmodified a linear polyamine of formula H2N-(RNH’)n-NH2, wherein R is -CH2-CH2-, having primary and secondary amine groups (claims 2-5, 7, and 9) and APTAC (claim 6), an activated olefin of the first claimed formula wherein R2 is H; X is NH; R3 is -CH2-CH2- (C2 alkyl); and Y is NR4R5R6(+), wherein R4, R5, and R6 are methyl (C1 alkyl)) to produce a compound having at least five positive charges (claim 10). Regarding claims 13-15, the claims of ‘681 recite PEI wherein each of five repeating variables (l, m, n, o, and p) can be between 1 and 100, which encompasses the claimed MW, and APTAC in claim 37. Regarding claims 16-21, the species of claim 24 and 38 is water soluble and is intended for use in aqueous compositions for washing textiles and can further comprise another functional ingredient, such as additional surfactants. See claims 30-33 and 40.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1-21 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-24 of U.S. Patent No. 11084974 (‘974).
Although the claims at issue are not identical, they are not patentably distinct from each other because claim 14 discloses the use of the species of claims 11 and 12. Said species are derived from derived from the reaction between an unmodified a linear polyamine of formula H2N-(RNH’)n-NH2, wherein R is -CH2-CH2-, having primary and secondary amine groups (claims 2-5, 7, and 9) and APTAC (claim 6), an activated olefin of the first claimed formula wherein R2 is H; X is NH; R3 is -CH2-CH2- (C2 alkyl); and Y is NR4R5R6(+), wherein R4, R5, and R6 are methyl (C1 alkyl)) to produce a compound having at least four positive charges (claims 1, 8, and 10). Regarding claims 13-15, see claims 2, 5, and 10. Regarding claims 16-21, see claims 15-24.
Claims 1-21 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-16 of U.S. Patent No. 11702586 (‘586).
Although the claims at issue are not identical, they are not patentably distinct from each other because claim 13 discloses a composition comprising the species of claims 11 and 12. Said species are derived from derived from the reaction between an unmodified a linear polyamine of formula H2N-(RNH’)n-NH2, wherein R is -CH2-CH2-, having primary and secondary amine groups (claims 2-5, 7, and 9) and APTAC (claim 6), an activated olefin of the first claimed formula wherein R2 is H; X is NH; R3 is -CH2-CH2- (C2 alkyl); and Y is NR4R5R6(+), wherein R4, R5, and R6 are methyl (C1 alkyl)) to produce a compound having at least four positive charges (claims 1, 8, and 10). Regarding claims 13-15, see claims 2, 4, 5, and 10 and 11. Regarding claims 16-21, see claims 14-16.
Claims 1-10 and 13-21 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-24 of U.S. Patent No. 11058111 (‘111).
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of ‘111 require the use of the instantly claimed compounds, wherein the polyamine is ethoxylated before or during the aza-Michael reaction (option iii in claim 3) and corresponds to compounds of formula H2N-(RNH’)n-NH2, wherein R is -CH2-CH2- or -CH2-CH2-OH, having primary, secondary, and tertiary amine groups (claims 2-5). The activated olefins include those from claim 6, including APTAC, an activated olefin of the first claimed formula wherein R2 is H; X is NH; R3 is -CH2-CH2- (C2 alkyl); and Y is NR4R5R6(+), wherein R4, R5, and R6 are methyl (C1 alkyl)) to produce a compound having at least four positive charges (claims 1, 8, and 10). See claims 6-7. Regarding claims 7, 9, and 13-15, see claims 4-6. Regarding claims 16-21, see claims 8-17.
Claims 1-10 and 13-21 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-32 of U.S. Patent No. 12082580 (‘580).
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of ‘580 require the use of the claimed compounds wherein the polyamine is ethoxylated before or during the aza-Michael reaction (option iii in claim 3) and corresponds to compounds of formula H2N-(RNH’)n-NH2, wherein R is -CH2-CH2- or -CH2-CH2-OH, having primary, secondary, and tertiary amine groups (claims 2-5). See claim 32. The activated olefins include those from claim 6, including APTAC, an activated olefin of the first claimed formula wherein R2 is H; X is NH; R3 is -CH2-CH2- (C2 alkyl); and Y is NR4R5R6(+), wherein R4, R5, and R6 are methyl (C1 alkyl)) to produce a compound having at least four positive charges (claims 1, 8, and 10). See claims 12-13. Regarding claims 7, 9, and 13-15, see claims 3-10. Regarding claims 16-21, see claims 15-24 and 32.
Claims 1-10 and 13-21 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-24 of U.S. Patent No. 11359291 (‘291).
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of ‘291 require the use of the claimed compounds wherein the polyamine is ethoxylated before or during the aza-Michael reaction (option iii in claim 3) and corresponds to compounds of formula H2N-(RNH’)n-NH2, wherein R is -CH2-CH2- or -CH2-CH2-OH, having primary, secondary, and tertiary amine groups (claims 2-5). The activated olefins include those from claim 6, including APTAC, an activated olefin of the first claimed formula wherein R2 is H; X is NH; R3 is -CH2-CH2- (C2 alkyl); and Y is NR4R5R6(+), wherein R4, R5, and R6 are methyl (C1 alkyl)) to produce a compound having at least four positive charges (claims 1, 8, and 10). See claims 2-11 Regarding claims 7, 9, and 13-15, see 2-13. Regarding claims 16-21, see claims 15-24.
Claims 1-10 and 13-21 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-20 of U.S. Patent No. 11639553 (‘553).
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of ‘553 require the use of the claimed compounds wherein the polyamine is ethoxylated before or during the aza-Michael reaction (option iii in claim 3) and corresponds to compounds of formula H2N-(RNH’)n-NH2, wherein R is -CH2-CH2- or -CH2-CH2-OH, having primary, secondary, and tertiary amine groups (claims 2-5). The activated olefins include those from claim 6, including APTAC, an activated olefin of the first claimed formula wherein R2 is H; X is NH; R3 is -CH2-CH2- (C2 alkyl); and Y is NR4R5R6(+), wherein R4, R5, and R6 are methyl (C1 alkyl)) to produce a compound having at least four positive charges (claims 1, 8, and 10). See claims 2-11 Regarding claims 7, 9, and 13-15, see 2-13. Regarding claims 16-21, see claims 15-20.
Claims 1-10 and 13-18 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-25 of U.S. Patent No. 11236040 (‘040).
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of ‘040 are directed toward the claimed compounds wherein the polyamine is ethoxylated before or during the aza-Michael reaction (option iii in claim 3) and corresponds to compounds of formula H2N-(RNH’)n-NH2, wherein R is -CH2-CH2- or -CH2-CH2-OH, having primary, secondary, and tertiary amine groups (claims 2-5). See claims 2-9. The activated olefins include those from claim 6, including APTAC, an activated olefin of the first claimed formula wherein R2 is H; X is NH; R3 is -CH2-CH2- (C2 alkyl); and Y is NR4R5R6(+), wherein R4, R5, and R6 are methyl (C1 alkyl)) to produce a compound having at least four positive charges (claims 1, 8, and 10). See claims 10-15. Regarding claims 7, 9, and 13-15, see claims 2-15 and 24. Regarding claims 16-18, the compound can be in a composition comprising other compounds. See claim 8.
Claims 1-10 and 16-21 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-20 of U.S. Patent No. 12202784 (‘784).
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of ‘784 are directed toward synthesizing the claimed compounds wherein the polyamine is ethoxylated before or during the aza-Michael reaction (option iii in claim 3) and corresponds to compounds of formula H2N-(RNH’)n-NH2, wherein R is -CH2-CH2- or -CH2-CH2-OH, having primary, secondary, and tertiary amine groups (claims 2-5). See claims 9-15. The activated olefins include those from claim 6, when the activated olefin of the first claimed formula wherein R2 has Y is NR4R5R6(+), wherein R4, R5, and R6 are methyl (C1 alkyl)) to produce a compound having one or more positive charges (claims 1, 8, and 10). See claims 1 and 16. Regarding claims 7 and 9, see claim 15. Regarding claims 16-21, see claims 16-20.
Claims 1-21 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-24 of U.S. Patent No. 11292734 (‘734).
Although the claims at issue are not identical, they are not patentably distinct from each other because claim 14 of ‘734 discloses a method which requires the species of claims 11 and 12. Said species are derived from derived from the reaction between an unmodified a linear polyamine of formula H2N-(RNH’)n-NH2, wherein R is -CH2-CH2-, having primary and secondary amine groups (claims 2-5, 7, and 9) and APTAC (claim 6), an activated olefin of the first claimed formula wherein R2 is H; X is NH; R3 is -CH2-CH2- (C2 alkyl); and Y is NR4R5R6(+), wherein R4, R5, and R6 are methyl (C1 alkyl)) to produce a compound having at least four positive charges (claims 1, 8, and 10). Regarding claims 13-15, see claim 15. Regarding claims 16-21, see claims 16-24.
Claims 1-21 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-24 of U.S. Patent No. 11926543 (‘543).
Although the claims at issue are not identical, they are not patentably distinct from each other because claim 13 of ‘543 discloses a composition which requires the species of claims 11 and 12. Said species are derived from derived from the reaction between an unmodified a linear polyamine of formula H2N-(RNH’)n-NH2, wherein R is -CH2-CH2-, having primary and secondary amine groups (claims 2-5, 7, and 9) and APTAC (claim 6), an activated olefin of the first claimed formula wherein R2 is H; X is NH; R3 is -CH2-CH2- (C2 alkyl); and Y is NR4R5R6(+), wherein R4, R5, and R6 are methyl (C1 alkyl)) to produce a compound having at least four positive charges (claims 1, 8, and 10). Regarding claims 13-15, see claim 14. Regarding claims 16-21, see claims 15-19.
Claims 1, 3, 4, 8, and 16-21 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-24 of U.S. Patent No. 11021383 (‘383).
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of ‘383 require the use of the claimed compounds wherein the polyamine is a modified or unmodified diamine of formula NH2-R11, wherein R11 is R1-Z-(CH2)m-, and Z is NH comprising a primary and secondary amine group. The activated olefin is a compound of the first formula in claim 1, wherein Y is NR4R5R6(+), and instant variables R2, X, and R3 correspond to the same variables in compound (I) of claim 1 (claims 1, 3, 4, and 8). Also see claim 8. Regarding claims 16-21, see claims 1 and 11-24.
Conclusion
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/AMY C BONAPARTE/Primary Examiner, Art Unit 1692