DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claims 1-20 are pending as amended on 1/12/2026. Claims 13-16 stand withdrawn from consideration.
The rejections under 35 USC 103 set forth below are the same as set forth in the action mailed on 11/20/2025. Modifications to the rejection under 35 USC 112(b) have been made to reflect the amendments to the claims. Therefore, this action is properly made final.
Any rejections and/or objections made in the previous Office action and not repeated below are hereby withdrawn. The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office Action.
Claim Objections
Claims 1 and 6 are objected to because of the following informalities:
In claim 1, the term “hydroxy carbon acid” in the third line of step (b) should be amended to read “hydroxycarboxylic acid.” Appropriate correction is required.
In claim 6, “(IIb)” in the location as shown with an arrow below should be changed to “(IIc)”:
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Claim Rejections - 35 USC § 112
Claims 6, 17 and 18 are 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.
Claims 6 recites a content of residue IIa, based on a total of all residues IIa, IIb and IIc attached to amino groups of the polyamine employed in step (a). However, residue IIa contains a residue according to IIb (see the portion of the IIa structure copied below within the rectangle added by the examiner) and a residue according to IIc (see the portion of the IIa structure copied below within the circle added by the examiner).
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Therefore, for every one residue IIa attached to an amino group of the polyamine employed in step (a) there must be one residue IIb (within the IIa structure) attached to the same amino group via units subscripted “p.” Similarly, for every one residue IIa attached to an amino group of the polyamine employed in step (a) there must be one residue IIc (within the IIa structure) attached to the same amino group via units subscripted “p” and “m.”
When calculating the weight percentage of IIa based on “all residues (IIa), (IIb) and (IIc)…”, it is not clear whether the amounts of IIb and IIc in the total residues (i.e., in the denominator) should include the weights of IIb and IIc residues which are present as partial structures of IIa residues (in which case, the percentage of IIa based on all residues could never equal 100%), or, whether the denominator should be a total of IIa residues, IIb residues directly attached (i.e., with no intervening structure) to an amino group and IIc residues directly attached (i.e., with no intervening structure) to an amino group (in which case, the percentage of IIa could be 100 mol%). Claims 17 and 18 are included in this rejection because they depend from claim 6 and are therefore indefinite for the same reason.
For examination purposes, the claim has been interpreted as requiring the open bonds shown at the left sides in each of formulas IIa, IIb and IIc to be directly bonded to a nitrogen atom with no intervening structure (such that each of the three formulas correspond to different, mutually exclusive, residues attached to amino groups of the polyalkyleneimine or polyamine). Claims 17 and 18 are included in this rejection because they depend from claim 6 and are therefore indefinite for the same reason.
Claim Rejections - 35 USC § 103
Claim(s) 1-7, 9-12 and 17-20 stand rejected under 35 U.S.C. 103 as being unpatentable over Dixon et al (US 2004/0068091) for the reasons previously made of record on 11/20/2025. The rejection is copied below:
Dixon discloses alkylene oxide-lactone copolymers [0001]. Dixon teaches that ester functionality introduced by the lactone enhances overall biodegradability (see [0004], as well as a comparison of Examples 1-3 to comparative Example 4 in [0032-36]), and that introducing lactone into the second block of the copolymer rather than the first enhances foam inhibiting properties [0005] (see also Example 5 and comparative example 6). Such copolymers find use as surfactants, emulsifiers, lubricants etc… [0002, 0027].
As to claims 1, 2, 9 and 12, Dixon discloses a block copolymer obtainable by polymerizing an alkylene oxide in the presence of an organic initiator to form a first block [0007]. Dixon teaches that the initiator can be polyfunctional, including having at least two NH2 groups (see formula (V) in [0023-24], where Y can be -NH- and b is at least 2), and can include diamines, such as ethylenediamine [0024]. Ethylenediamine is a polyamine as recited in claim 1, and has a formula according to instant formula (I) in claim 2 (and meeting instant claim 9) wherein instant R is C2 alkylene, and instant y and z are each 0.
As to instant step a):
Dixon teaches that the number of monomer units in each of the first and second blocks may range from 1 to 100 [0011]. See also claim 9. One having ordinary skill in the art would have recognized that the number of alkylene oxide (monomer) units in Dixon’s first blocks corresponds to the moles of alkylene oxide which are reacted per mole of functional (e.g., -NH) group on the initiator.
The person having ordinary skill in the art would have been motivated to select any appropriate number of units within Dixon’s disclosed range in order to provide an intermediate suitable for further reaction to form a second block (as taught by Dixon in [0031]) for the ultimate preparation of surfactants, emulsifiers, lubricants etc… (see [0002]). It would have been obvious to the person having ordinary skill in the art to have formed Dixon’s block copolymer having any number of alkylene oxide units in the first block within Dixon’s disclosed range of 1 to 100, including any number within a range of 1 to 7 alkylene oxide units (or within a range of 1 to 2 alkylene oxide units), thereby meeting the range recited in step a) in instant claim 1 (or in instant claim 12). The reaction of ethylenediamine initiator with 1 to 7 (or 1 to 2) moles of alkylene oxide per -NH functionality (in order to form a first block having 1 to 7 (or 1 to 2) alkylene oxide units) corresponds to instant step (a) recited in claim 1. Case law has established that a prima facie case of obviousness is established where the claimed ranges overlap the ranges disclosed by the prior art. See MPEP 2144.05.
As to instant step b):
Dixon teaches reacting the first block with alkylene oxide and lactone to form a second block [0030-31], and teaches that the second block can comprise alternate blocks of alkylene oxide and lactone by reacting the first block alternately with either alkylene oxide or lactone [0031]. Dixon further teaches that each block comprises at least 3 units of alkylene oxide or 2 units of lactone [0031]. One having ordinary skill in the art would have recognized that the number of lactone (monomer) units in each block within Dixon’s second blocks corresponds to the moles of lactone which are reacted per mole of functional group on the intermediate (which also corresponds to moles of lactone per mole of NH-functionality on the diamine initiator).
When reacting the functional groups of the first block (i.e., the end groups of Dixon’s intermediate formed by reaction of ethylenediamine with alkylene oxide) with lactone to form a block having at least two units thereof, as taught by Dixon in [0031], the person having ordinary skill in the art would have been motivated to select any number of moles of lactone per NH-functionality within Dixon’s disclosed range in order to provide an intermediate suitable for further reaction to provide a block of alkylene oxide units, as taught by Dixon in [0031], for the ultimate preparation of surfactants, emulsifiers, lubricants etc. (see [0002]). It would have been obvious to the person having ordinary skill in the art, therefore, to have selected any number of moles of lactone per NH-functionality within Dixon’s range of at least 2, including a number meeting the range recited in step b) of claim 1 (i.e., 2 to 10) or claim 12 (i.e., 2 to 3). Case law has established that a prima facie case of obviousness is established where the claimed ranges overlap the ranges disclosed by the prior art. See MPEP 2144.05.
As to instant step c):
In Dixon’s disclosed process [0031] wherein a second block is formed by reacting a first block alternately with either alkylene oxide or lactone, the reaction of a formed lactone block (i.e., as discussed in the preceding paragraph) with sufficient alkylene oxide to form a block comprising at least three units of alkylene oxide (as taught by Dixon in [0031]) corresponds to instant step (c) (i.e., in order to form at least three units of alkylene oxide in a block thereof, at least 3 moles of alkylene oxide must be employed per mole of -NH functionality in the initiator, which falls within the presently claimed range of at least 1 mole). [Alternatively, it would have been obvious to the person having ordinary skill in the art to have reacted the formed lactone block with any number of moles of alkylene oxide within Dixon’s range of at least 3 (as taught by Dixon in [0031]), including a number meeting the range recited in step c) of instant claim 12 (i.e., 5 to 30 mol), in order to provide an intermediate suitable for the ultimate preparation of surfactants, emulsifiers, lubricants etc. (see [0002]).]
Given that Dixon suggests a process comprising steps corresponding to instant product-by-process steps a), b) and c) as set forth above, Dixon suggests an alkoxylated polyamine product meeting the instant claims.
As to instant claims 3-5 and 11, Dixon suggests an alkoxylated polyamine according to claim 1, as set forth above, wherein a first block is formed by reaction of ethylenediamine with 1 to 7 moles of alkylene oxide, and a second block is formed by reaction of the first block with 2 to 10 moles of lactone, followed by reaction with at least 3 moles of alkylene oxide. Dixon discloses a preferred embodiment wherein ethylene oxide is used to form the first block, while propylene oxide or butylene oxide is used to form the second block [0013]. Dixon discloses caprolactone as the preferred lactone [0018-19]. An alkoxylated polyamine formed by reaction of ethylenediamine with ethylene oxide to form the first block, followed by alternating reactions of caprolactone and then alkylene oxide (either propylene oxide or butylene oxide) to form the second block, as suggested by Dixon, has residues according to instant formula IIa, IIb and IIc wherein R4 (derived from ethylene oxide) is C2 alkylene, R3 (derived from caprolactone) is C5 alkylene, R1 (derived from propylene oxide or butylene oxide) is C3 or C4 alkylene and R2 (derived from the hydroxyl end group on the terminal alkylene oxide unit) is hydrogen.
As to the values of instant “p” (units of alkylene oxide in the first block), instant “m” (units of lactone reacted with the first block) and instant “n” (units of alkylene oxide reacted with the lactone block), the person having ordinary skill in the art would have been motivated to select any number of alkylene oxide units for the formation of Dixon’s first block within Dixon’s disclosed range of 1 to 100, any number of lactone units for reaction with the first block within Dixon’s disclosed range of at least 2, and any number of alkylene oxide units for reaction with the block formed from lactone within Dixon’s disclosed range of at least 3, in order to provide a copolymer having desired properties such as biodegradability, foaming, and cloud point temperature (see Examples [0032-37]), and suitable for use as a surfactant, emulsifier, lubricant etc… (see [0002]). It would have been obvious to the person having ordinary skill in the art, therefore, to have selected any number of alkylene oxide units for the formation of Dixon’s first block within Dixon’s disclosed range of 1 to 100, including 1 to 5 alkylene oxide units (meeting instant “p”), any number of lactone units for reaction with the first block within Dixon’s disclosed range of at least 2, including 2 to 10 (meeting instant “m”), and any number of alkylene oxide units for reaction with the block formed from lactone within Dixon’s disclosed range of at least 3, including 3 to 100 (meeting instant “n”), thereby arriving at a residue according to instant residue IIa (within which are residues according to instant formulas IIb and IIc). Case law has established that a prima facie case of obviousness is established where the claimed ranges overlap the ranges disclosed by the prior art. See MPEP 2144.05.
As to claims 6, 17 and 18, Dixon suggests an alkoxylated polyamine according to claim 3, as set forth above, wherein both amine groups of the ethylenediamine are attached to residues according to instant formula IIa (i.e., a residue according to IIa accounts for 100 wt% of all residues, meeting the presently claimed ranges).
As to claim 7, Dixon suggests an alkoxylated polyamine according to claim 2, as set forth above. The alkoxylated polyamine suggested by Dixon meets instant claim 7 for at least the reason that ethylenediamine has a molecular weight of 60 g/mol, which falls within the claimed range of 50 to 10,000 g/mol.
As to claim 10, Dixon does not teach quaternization of nitrogen atoms, and therefore suggests an alkoxylated polyamine according to claim 1 wherein 0% of the nitrogen atoms are quaternized (which falls within the presently claimed range of up to 100%).
As to claims 19 and 20, Dixon suggests an alkoxylated polyamine according to claim 1, as set forth above. The alkoxylated polyamine suggested by Dixon meets instant claims 19 and 20 for at least the reason that Dixon discloses carrying out the polymerization of alkylene oxide (corresponding to instant step a) in the presence of a catalyst, particularly potassium hydroxide (i.e., a base catalyst) [0025].
Claim(s) 8 is/are rejected under 35 U.S.C. 103 as being unpatentable over Dixon et al (US 2004/0068091) in view of Ebert et al (US 2016/0222160).
The rejection above over Dixon is incorporated here by reference.
Dixon suggests an alkoxylated polyamine according to claims 1 and 2, as set forth above. As established, Dixon teaches a variety of types of polyfunctional initiator compounds in [0023-24], including ethylenediamine. However, Dixon fails to teach a polyalkylene imine initiator.
Ebert teaches that polyamines modified with alkyleneoxy units are known in the art to be suitable as soil dispersants in cleaning compositions [0002, 0006, 0007] and as breakers for crude oil emulsions [0005]. Like Dixon, Ebert names diamines (including ethylenediamine) as an example of a polyamine which can be reacted with alkylene oxide [0030]. Ebert also teaches that the polyamine backbone can comprise primary, secondary and tertiary amine nitrogen atoms [0026], i.e., a polyalkyleneimine having a molecular weight from 250-5000 g/mol [0032]. Ebert discloses a general formula (I) which encompasses both alkoxylated polyamines such as ethylenediamine (see [0011], wherein R can be C2 alkylene [0012] and y and z can be 0 [0024]), and, alkoxylated polyalkyleneimines (see [0011], wherein y and z are each 0 to 150 [0019], R can be C2-12 alkylene, and B is a continuation of polyalkyleneimine by branching [0012-15]). Polyethyleneimine (i.e., PEI, wherein R is ethylene) having a MW of 600 g/mol is utilized in Ebert’s examples [0107]; PEI600 has a structure according to instant formula I recited in claims 2 and 8 wherein R is ethylene, and (in view of the molecular weight being 600 g/mol) the PEI must have a total of y+z units within the recited range of 9 to 120.
Considering Ebert’s disclosure, polyalkyleneimines (such as PEI) and polyamines (such as ethylenediamine) were both known in the art as polyamine backbones suitable for modifying by alkoxylation. Given Dixon’s broad disclosure with regard to suitable polyfunctional initiator compounds, the person having ordinary skill in the art would have been motivated to substitute the ethylenediamine initiator named by Dixon for any appropriate polyfunctional initiator compound known in the art to be likewise suited for modifying by alkoxylation. One would have had a reasonable expectation of success in doing so given that both initiators are taught to be suitable by Ebert, and, the person having ordinary skill in the art would have been motivated to substitute ethylenediamine for an initiator such as polyethyleneimine in order to provide a polyfunctional initiator (as taught by Dixon) having an increased number of functional groups available for initiation of block formation. It would have been obvious to the person having ordinary skill in the art, therefore, to have modified a polyfunctional initiator by reaction with alkylene oxide and lactone, as suggested by Dixon, by utilizing polyethyleneimine (as taught/exemplified by Ebert) as Dixon’s polyfunctional initiator, thereby arriving at the presently claimed subject matter.
Double Patenting
Claims 1-12 and 17-20 stand provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over the claims of copending Application No. 18/257633 (reference application). The reasons for rejection are the same as previously set forth in the action mailed on 11/20/2025.
Claims 1-9, 11, 12 and 17-20 stand rejected on the ground of nonstatutory double patenting as being unpatentable over the claims of U.S. Patent No. 12545857 Although the claims at issue are not identical, they are not patentably distinct from each other. The reasons for rejection are the same as previously set forth in the provisional nonstatutory double patenting rejection over application No. 18/338406, which is now US Patent No. 12545857.
Response to Arguments
Applicant's arguments filed 1/12/2026 have been fully considered.
Applicant argues (p 12) that the rejection over Dixon fails due to a “cardinal error in its analysis.” Applicant argues (p 13) that in Dixon, the organic initiator (e.g., the ethylenediamine) does not otherwise become part of the block polymer. Applicant argues that Dixon’s initiator merely initiates the polymerization process and is possibly incorporated at the very end of a polymer, while the claimed polyamine “is an integral monomer subunit of the synthesized novel polymer.”
However, the polyamine or polyalkyleneimine reacted in step (a) of instant claim 1 functions as an initiator, just like the polyamine (ethylenediamine) in Dixon. When a ring opening polymerization of an alkylene oxide and/or lactone monomer is initiated utilizing a monofunctional initiator with a single reactive hydrogen (e.g., an initiator containing a single OH or single NH group), a single polymer chain grows from the reactive hydrogen of the initiator, such that the initiator is incorporated at one end of the polymer. However, when utilizing a polyfunctional initiator having at least two reactive hydrogens as taught by Dixon in [0023] (and as recited in step (a) of claim 1), a polymer chain grows from each reactive hydrogen on the initiator, such that the initiator becomes centrally incorporated in the synthesized polymer. Both the polyamine recited in step (a) of claim 1 and the ethylenediamine disclosed by Dixon are polyfunctional initiators which become centrally incorporated: each of the amino groups on the polyamine has a reactive hydrogen which initiates a ring opening alkoxylation of alkylene oxide. There is no fundamental difference between the ethylenediamine polyfunctional initiator disclosed by Dixon and the polyamine initiator recited in step (a) of claim 1.
Applicant further argues (p 13) that the term “alkoxylated” does not appear in Dixon even once. The fact that the specific term “alkoxylated” does not appear in Dixon, in and of itself, is not sufficient to establish that an alkoxylated initiator (e.g., alkoxylated polyamine) is not formed by reacting an alkylene oxide and initiator (see Dixon [0020]). Moreover, after naming preferred initiators, including ethylenediamine, as examples of polyfunctional initiators in [0023-4], Dixon states “Such compounds may also be ethoxylated.” This means that the named initiators can be reacted with ethylene oxide (i.e., an alkylene oxide) such that they become “ethoxylated” (i.e., alkoxylated).
Applicant further argues (p 13) that Dixon’s ethylenediamine does not possess a plurality of nitrogen atoms. This argument is unpersuasive for at least the reason that ethylenediamine possesses two nitrogen atoms, which is a plurality. Further note that the term “polyamine” recited in instant claim 1 (as well as the structural formula (I) further limiting the “polyamine” recited in instant claim 2) encompasses ethylenediamine.
As to the double patenting rejections: Applicant's request for abeyance is acknowledged to the extent that Applicant's lack of response to the cited rejections will not be treated as non-responsive under 37 CFR 1.111(b). However, since the rejections are considered proper they will be maintained until such time as a complete response to them is filed or conditions appropriate for removal of the rejections are present. See MPEP 804(I)(B)(1).
Conclusion
Applicant's amendment necessitated the modified ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL KAHN whose telephone number is (571)270-7346. The examiner can normally be reached Monday to Friday, 8-5.
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/RACHEL KAHN/ Primary Examiner, Art Unit 1766
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