DETAILED ACTION
Response to Arguments
Applicant's arguments filed October 20, 2025 have been fully considered but they are not persuasive.
A) Applicants argue that amended claim 1 differs from Cleary et al. in four ways (pg. 7 of remarks). Features 1-3 have been addressed in previous actions. In feature 4, applicants argue that the weight average molecular weight is claimed to be 600-1,000 g/mol. Applicant’s admit that Cleary et al. teaches the molecular weight in Cleary et al. is given as 600 to 25,000 g/mol which overlaps the claimed range. In the case where the claimed ranges overlap or lie inside ranges disclosed by the prior art, a prima facie case of obviousness exists (MPEP 2144.05 I). Applicants can rebut a prima facie case of obviousness by showing the criticality of the range with evidence (MPEP 2144.05 III A). Argument does not replace evidence where evidence is necessary (MPEP 2145 I).
B) Applicant’s argument that the unexpected results are present when the alkoxylated compounds have a terminal polybutylene oxide block is not persuasive. Objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support. In other words, the showing of unexpected results must occur over the entire range claimed (MPEP 716.02(d)). In the instant case, only two of all the claimed alkoxylated polyalkylene imine or polyamine that allegedly fall within the claimed invention are tested. However, the instant specification does not provide what each of the variable moieties in example 1 and example 2 are, so it is unclear if the processes in examples 1 and 2 actually do fall within the claimed polymer. Further, only one example outside of the claimed polymer is tested, comparative example 3, but again the variables are not provided so it is unknown the structure of this polymer. Arguments presented by the applicant cannot take the place of evidence in the record. Argument does not replace evidence where evidence is necessary (MPEP 2145 I). Further, the examiner’s explanation of why examples 1, 2 and 3 cannot be relied on as evidence (namely that the specification does not teach what the variable moieties actually are, so it is unknown which examples overlap the claims, and how commensurate in scope they are), was set forth in the previous rejection but was not explained in the current remarks. Arguments presented by applicant cannot take the place of evidence in the record (MPEP 2145 I).
C) Applicant’s argument that the prior art did not teach the advantageous properties of the claimed polymer is not persuasive. The Court in KSR stated that it is an error to look only to the particular problem the patentee was trying to solve. The problem motivating the patentee may be only one of many addressed by the patent’s subject matter and a person having ordinary skill in the art would not be led only to those elements of the prior art designed to solve the same problem (MPEP 2141 II A2). A rejection under 35 U.S.C. 103(a) is based upon a combination of references; the reason or motivation to modify the prior art reference(s) may often suggest what the inventor has done, but for a different purpose or to solve a different problem. Furthermore, it is noted that it is not necessary that the prior art suggest the combination to achieve the same advantage or result discovered by the applicant. The motivation question arises in the context of the general problem confronting the inventor, rather than the specific problem solved by the invention. The motivation statement for the combination of references can be found in the rejection below.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
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, 2, 5-7, 12, 13 and 14 are rejected under 35 U.S.C. 103 as being unpatentable over Cleary et al. (U.S. Pat. 6,127,331) in view of Kirkpatrick et al. (U.S. Pat. 3,152,188).
Regarding claims 1 and 2: Cleary et al. teaches an alkoxylated polyalkylene imine (title) of the general formula (I) (abstract) where R is a C2-C6 linear or branched alkylene (abstract), B represents a continuation of the chain structure by branching (col. 3 lines 15-20), x and y (which correspond to the claimed y and z, respectively) are about 4 to 200 (col. 2 lines 15-20), which overlaps the claimed range. The moiety E is
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(col. 2 lines 10-15), where R1 can be 1,2-butylene, R2 is ethylene and R3 is hydrogen or C1-C4 alkyl (col. 3 lines 40-45). The variable m (which is the claimed n) is 1-10 and n (which is the claimed m) is 10-40 (col. 4 lines 5-10). Cleary et al. teaches the molecular weight for the polyamine backbone is 600-25,000 g/mol (col. 4 lines 16-20), which overlaps the claimed range.
This alkoxylated polyalkylene imine is different than the claimed structure in that the butylene oxide units are directly bonded to the nitrogen followed by the ethylene oxide groups, whereas in the claim, the ethylene oxide groups are bonded to the nitrogen followed by the butylene oxide groups. However, Kirkpatrick et al. teaches a similar alkoxylated polyalkylene imine where the ethylene oxide is first reacted to the amine followed by the butylene oxide (example I). Cleary et al. and Kirkpatrick et al. are analogous art since they are both concerned with the same field of endeavor, namely alkoxylated polyalkylene imine resins that have been alkoxylated with ethylene and butylene. At the time of the invention a person having ordinary skill in the art would have found it obvious to react the ethylene oxide units first and then the butylene oxide units as in Kirkpatrick et al. and would have been motivated to do so since Kirkpatrick et al. teaches this sequential addition gives reproducible results and that one skilled in the art can change the order of the steps depending on the type of composition desired (col. 3 lines 10-25).
Regarding claim 5: Cleary et al. teaches R is ethylene (col. 4 line 26), and x and y (which correspond to the claimed y and z, respectively) are about 4 to 200 (col. 2 lines 15-20), which overlaps the claimed range.
Regarding claims 6 and 7: Cleary et al. teaches R is ethylene (col. 4 line 26), and x and y (which correspond to the claimed y and z, respectively) are about 4 to 200 (col. 2 lines 15-20), which overlaps the claimed range. Cleary et al. teaches 1,2-butylene (col. 3 lines 40-41), R2, which is R3 in the art, is hydrogen or C1-C4 alkyl (col. 3 lines 40-45), the variable m, which is the claimed variable n, is 1-10, and n, which is the claimed variable m, is 10-40 (col. 4 lines 5-10), which overlaps the claimed ranges.
Regarding claim 12: Cleary et al. teaches the polymer can be used for laundry detergent (col. 1 lines 5-10), which can remove oil (col. 1 lines 10-15). Crude oil is a type of oil.
Regarding claim 13: Cleary et al. teaches the basic claimed alkoxylated polyalkylene imine as set forth above. Not disclosed is first reacting the polyalkylene imine with ethylene oxide and then with butylene oxide. However, Kirkpatrick et al. teaches a similar alkoxylated polyalkylene imine where the ethylene oxide is first reacted to the amine followed by the butylene oxide (example I). At the time of the invention a person having ordinary skill in the art would have found it obvious to react the ethylene oxide units first and then the butylene oxide units as in Kirkpatrick et al. and would have been motivated to do so since Kirkpatrick et al. teaches this sequential addition gives reproducible results and that one skilled in the art can change the order of the steps depending on the type of composition desired (col. 3 lines 10-25).
Regarding claim 14: Cleary et al. teaches 1,2-butylene (col. 3 lines 40-41), the variable m, which is the claimed variable n and corresponds to the butylene oxide units, is 1-10, and n, which is the claimed variable m and corresponds to the ethylene oxide units, is 10-40 (col. 4 lines 5-10), which overlaps the claimed ranges.
Claims 8-10 are rejected under 35 U.S.C. 103 as being unpatentable over Cleary et al. (U.S. Pat. 6,127,331) in view of Kirkpatrick et al. (U.S. Pat. 3,152,188) as applied to the claims set forth above and in view of Kumar et al. (US 2017/0267585).
Regarding claims 8-10: Cleary et al. teaches the basic claimed alkoxylated polyamine set forth above. Not disclosed are when y and z are both 0 and R is linear hexamethylene. However, Kumar et al. teaches a similar alkoxylated polyamine with the base amine being hexamethylenediamine (para. 42) capped with ethylene oxide and butylene oxide units (para. 43). Cleary et al. and Kumar et al. are analogous art since they are both concerned with the same field of endeavor, namely alkoxylated polyamines. At the time of the invention a person having ordinary skill in the art would have found it obvious to use the hexamethylenediamine of Kumar et al. in the polyamine of Cleary et al. and would have been motivated to do so in order to lower the molecular weight of the polyamine as evidenced by Kumar et al. (para. 42).
Claims 11 and 15 are rejected under 35 U.S.C. 103 as being unpatentable over Cleary et al. (U.S. Pat. 6,127,331) in view of Kirkpatrick et al. (U.S. Pat. 3,152,188) as applied to the claims set forth above and in view of Ebert et al. (US 2016/0222160).
Regarding claims 11 and 15: Cleary et al. teaches the basic claimed alkoxylated polyalkylene imine as set forth above. Not disclosed is the quaternization of the nitrogen atoms. However, Ebert et al. teaches a similar alkoxylated polyalkyleneimine that has been quaternized, up to 100%, in particular 10-95% (para. 71). Cleary et al. and Ebert et al. are analogous art since they are both concerned with the same field of endeavor, namely alkoxylated polyalkylene imines. At the time of the invention a person having ordinary skill in the art would have found it obvious to quaternize the nitrogen atoms in Cleary et al. as in Ebert et al. and would have been motivated to do so since Ebert et al. teaches quaternization achieves better compatibility and phase stability (para. 72).
Conclusion
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Contact Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Megan McCulley whose telephone number is (571)270-3292. The examiner can normally be reached Monday - Friday 9-5:30.
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/MEGAN MCCULLEY/Primary Examiner, Art Unit 1767