DETALIED ACTION
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 3/17/26has been entered.
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA . Per amendment dated 2/18/26, claims 14, 17-32 are currently pending in the application, with claims 24-26 being withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim.
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 18, 19, 27-30 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 18, 19, 27-30 depend on claim 14 and recite the limitation "weight based on the total weight of the amount of (meth)acrylic acid and C₁ to C₈ alkyl (meth)acrylates present in the mixture". It is noted that the recitation “(meth)acrylic acid and/or C1 to C8 alkyl (meth)acrylates” in claim 14 encompasses three different embodiments, i.e., (1) (meth)acrylic acid; (2) C1 to C8 alkyl (meth)acrylates, and (3) (meth)acrylic acid and C1 to C8 alkyl (meth)acrylates. Claims 18, 19, 27-30 are indefinite with embodiments (1) and (2), where only (meth)acrylic acid or C1 to C8 alkyl (meth)acrylates would be present in the mixture. However, the weight basis recited in claims 18, 19, 27-30 corresponds to the total weight of the amount of (meth)acrylic acid and C₁ to C₈ alkyl (meth)acrylates present in the mixture when embodiments (1) and (2) include only one species
For the purpose of examination, Examiner interprets the limitation in claims 18, 19, 27-30 to mean "weight based on the total weight of the amount of (meth)acrylic acid and/or C₁ to C₈ alkyl (meth)acrylates present in the mixture".
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.
Claims 14, 17-19, 22, 23, 27-32 are rejected under 35 U.S.C. 103 as being unpatentable over Bueschel et al. (WO 2007063031 A2, machine translation, of record).
Regarding claims 14, 31 and 32, Bueschel teaches mixtures of polymerizable compounds with stabilizers. Disclosed mixtures comprise: (A) at least one aromatic heterocycle of the following general formula (I), and (B) at least one polymerizable compound:
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wherein, W, X and Y independently of one another, may be for e.g., H, C1-C20 alkyl, C3-C15 cycloalkyl, C2-C20 alkylcarbonyl or OR3, wherein R3 may be H (i.e., X may be OR3=OH), and Z may be any of H, C1-C20 alkyl, C3-C15 cycloalkyl (Ab., pages 1-2, page 3-last paragraph, page 7- 5th paragraph, Examples, ref. claims).
Disclosed genus of polymerizable compound (B) includes (meth)acrylic acid and C1-C20 alkyls esters thereof (page 17- 2nd and 3rd paragraphs, pages 31-32, ref. claim 12).
Disclosed examples 1-3 are drawn to the following aromatic heterocycles (A), that are mixed with and acrylic acid (B) (page 23, TABLE 1):
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Bueschel is silent on a mixture comprising an aromatic heterocycle (A) that falls within the scope of the claimed invention, in one single embodiment as claimed.
At the outset, it is noted that in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. See MPEP § 2144.05.
Given the generic teaching on the scope of W, X, Y and Z in the aromatic heterocycle (A) of formula (I) for stabilizing (meth)acrylic acid and/or alkyl (meth)acrylates, it would have been obvious to one of ordinary skill in the art, as of the effective filing date of the claimed invention, to prepare stabilized (meth)acrylic acid and/or alkyl (meth)acrylates using any of the disclosed compounds of formula (I), including those within the scope of the claimed invention. For instance, in reference to the disclosed formula (1), Examples 1-3 teach a hydroxyl group as X group with sufficient specificity, Compound 2 teaches Y as a methyl (i.e., at claimed R7 position), and Compound 3 teaches W as a methyl (C1 alkyl, i.e., at claimed R8 position). In addition, given the teaching in the general disclosure on an alkyl as being equally suitable at both, the W and Y positions in formula (I), and the teaching on an aryl and an alkyl group to be equally suitable at Z position, i.e., equivalence of the groups, it would have been within the level of ordinary skill in the art to prepare compounds of formula (I), for e.g., by substituting the aryl groups in the exemplified compounds with alkyl groups, absent evidence to the contrary.
Regarding claim 17, Bueschel teaches (meth)acrylic acid and thus the claimed species do not necessarily limit the scope of claim 14 which recites “(meth)acrylic acid and/or C1 to C8 alkyl (meth)acrylates”. Even so, Bueschel teaches methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate etc. as polymerizable compounds (page 17-last paragraph).
Regarding claims 18, 19, 27-30, Bueschel teaches the aromatic heterocyclic compound of formula (I) (A) in an amount of 0.1 to 1000 ppm, based on the polymerizable compound (page 20-last paragraph, ref. claim 5). Additionally, regarding claims 19, 27-30, given the teaching on (meth) acrylic acid, methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate etc. as suitable polymerizable compounds (page 17), and the range prescribed for heterocyclic compound (A), a skilled artisan would have found it obvious to select any of the disclosed monomers and any amount of the aromatic heterocyclic compound, including those within the scope of the claimed invention.
Regarding claims 22 and 23, Bueschel teaches oxygen-containing gases as costabilizers during storage and transport of the mixture (page 10-1st paragraph, page 15- last paragraph, page 22-1st and 2nd paragraphs, ref. claims 6 and 7).
Claim 20 is rejected under 35 U.S.C. 103 as being unpatentable over Bueschel et al. (WO 2007063031 A2, machine translation), in view of Yamaguchi et al. (JP 2002-179617A, machine translation) (references of record).
The discussion on Bueschel from preceding paragraphs as applied to claim 14 is incorporated herein by reference.
Bueschel is silent on a mixture comprising (meth)acrylic acid and one or more of the claimed components a. to i. as claimed.
As stated in paragraph 10 above, in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists.
The secondary reference to Yamaguchi teaches high purity acrylic acid and a method of producing the same. Yamaguchi recognizes that acrylic acid is used as raw a material for various copolymers, that the content of impurities is to be strictly limited depending on the application, and that a large amount of aldehyde is inferior in polymerization and the water content is also desired to be as small as possible. Yamaguchi teaches a method that provides for that acrylic acid comprising 300 ppm or less water (reads on component a.), and 20 ppm or less aldehydes, preferably less than 1 ppm (reads on component e.), which is stable to polymerization for an year (Overview, [0010]-[0011], ref. claim 4, [0044]-[0045]).
In view of the teaching in Yamaguchi on high purity acrylic acid and advantages thereof, it would have been obvious to one of ordinary skill in the art, as of the effective filing date of the claimed invention, to prepare a mixture comprising an aromatic heterocycle (A), including those within the scope of claim 14, and a monomer comprising acrylic acid comprising 300 ppm or less water and aldehydes at less than 1 ppm, including those within the scope of the claimed invention.
Claim 21 is rejected under 35 U.S.C. 103 as being unpatentable over Bueschel et al. (WO 2007063031 A2, machine translation, of record), in view of either Takasaki et al. (US 2008/0011385 A1) or Julka et al. (MY 121680 A).
The discussion on Bueschel from preceding paragraphs as applied to claims 14 and 17 is incorporated herein by reference.
Bueschel is silent on a mixture comprising claimed (meth)acrylate esters and one or more of the claimed components a. to f.
As stated in paragraph 10 above, in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists.
The secondary reference to Takasaki teaches a method of storing alkyl esters of (meth)acrylates in carbon coated steel tanks that are less expensive and highly versatile material without losing storage stability of the stored (meth)acrylate (Ab.). Disclosed alkyl esters of (meth)acrylates include methyl ester, ethyl ester, butyl ester etc. [0015], and a tank supplied with gas including oxygen having a water content of 100 ppm or less, preferably 10 to 100 ppm, so as to suppress the corrosion of the tank made of steel material [0023]. Takasaki prescribes (meth)acrylates having a concentration of (meth)acrylic acid at 30 ppm or less, to minimize the corrosion of the carbon coated steel [0027].
Given the advantages in Takasaki on adjusting the water content and (meth)acrylic acid content in alkyl (meth)acrylates when storing, it would have been obvious to one of ordinary skill in the art, as of the effective filing date of the claimed invention, to prepare a mixture comprising an aromatic heterocycle (A), including those within the scope of claim 14, an alkyl (meth)acrylate comprising less than 100 ppm or less of (meth)acrylic acid as the polymerizable compound (B), and to utilize a gas including oxygen having a water content of 100 ppm or less, when intended to store in carbon coated steel tanks.
In the alternative, the secondary reference to Julka teaches a process for refining butyl acrylate to a purity of 99 wt.% or more, and less than 1000, preferably less than 200 ppmw, of dibutyl ether (reads on component f.), and 500 ppmw or less of butyl acetate (reads on component e.) (page 5, lines 1-11). Julka teaches that butyl acrylate of high purity is desired because dibutyl ether and butyl acetate as impurities therein can impart odor to butyl acrylate (page 3, lines 1-8).
In view of the teachings of in Julka on advantages of butyl acrylate having dibutyl ether and butyl acetate contents within the disclosed ranges, it would have been obvious to one of ordinary skill in the art, as of the effective filing date of the claimed invention, to prepare a mixture comprising an aromatic heterocycle (A), including those within the scope of claim 14, and butyl acrylate comprising less than 200 ppmw dibutyl ether and less than 500 ppmw butyl acetate as the polymerizable compound (B).
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.
Claims 14, 17-19, 22, 27-32 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 16-30 of copending Application No. 18/287317 (reference application, preliminary amendment dated 10/18/23).
Although the claims at issue are not identical, they are not patentably distinct from each other because copending claim 16 is drawn to a mixture comprising at least one compound of formula (I), and at least polymerizable compound. The compound of formula (I) falls within the scope of general formula (II) of instant claims 14, 31 and 32. Additionally, dependent copending claim 23 recites acrylic and/or methacrylic acid as the polymerizable compound, and dependent copending claim 25 recites methyl acrylate, methyl methacrylate, ethyl acrylate, n-butyl acrylate and/or 2-ethylhexyl acrylate as the polymerizable compound. Thus, mixtures of copending claims 23 and 25 fall within the scope of instant claims 14, 17 and 31. Additionally, instant claim 18 encompasses the range as recited in copending claim 26, and claims 29 and 30 are encompassed by copending claims 24 or 26.
Regarding claims 19, 22, 27 and 28, although copending claims are silent on the claimed mixture in one single embodiment, copending claim 22, in view of copending claim 23 or 25 obviates instant claim 19, copending claim 29, in view of copending claim 23 claim 25 obviates instant claim 22, while copending claim 26 obviates the claims 27 and 28. As stated in paragraph 10 above, in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists.
Regarding claim 32, although copending claims are silent on the claimed mixture in one single embodiment, noting that R1 and R3 of formula (I) of copending claim 16 overlap in scope with R6 and R8 of formula (I) of instant claim 32, and given that R2 in formula (I) of copending 16 is a homolog of the claimed R7 of formula (I) of instant claim 32, it would have been obvious to one of ordinary skill in the art that copending claim 16, in view of copending claim 23 or 25 obviates the claimed limitation. Homologs “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).
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Response to Arguments
In view of the amendment 9/11/25, the objections of record are withdrawn and rewritten relying on the art of record. Applicant’s arguments have been duly considered.
Applicant argues that a broad genus or overlapping ranges does not render a specific selection obvious unless there is a clear teaching or motivation to select those values for the same purpose, that Bueschel allows for hundreds of potential combinations for variables W through Z and there is insufficient suggestion in the Bueschel reference to lead the ordinary skilled artisan to the specific compounds claimed here in a manner sufficient to form prima facie obviousness. Referring to the as-filed specification, Applicant asserts that the evidence of unexpected effects of the compounds encompassed by the claims as amended, correspond closely to the data presented in the specification as originally filed.
In response, Examiner’s response to arguments presented in the final office action dated 11/19/25 are incorporated herein by reference. Additionally, although Beuschel’s heterocyclic compounds of formula (I) are of a broad scope, the exemplified compounds (1) to (3), in view of the scope of substituents W, Y and Z in formula (I) taught in the general disclosure, render obvious the claimed compounds. Specifically, Bueshel’s compounds of Examples (1) (2) and (3) are as follows:
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In each of these compounds, the OH group is placed at the same position and in the claimed formula (II). While Compounds (2) and (3) include a CH3 substituent on one of carbon atoms adjacent to the carbon bearing the hydroxyl (i.e., corresponding to the claimed R7 or R8 positions in claimed formula (II)), Bueschel’s general formula (I) is open to an alkyl substituent being present on both carbon atoms adjacent to the carbon bearing the hydroxyl (i.e., both R7 and R8 positions may be a CH3 as in the claimed invention). Furthermore, although the disclosed compounds include a phenyl substituent on the nitrogen atom, Bueschel teaches an alkyl and an aryl group to be equally suitable as a substituent on the nitrogen atom. Thus, a skilled artisan would have found it obvious to prepare compounds wherein, for e.g., all the substituents on the heterocyclic ring are an alkyl group, e.g., methyl, absent evidence to the contrary.
Regarding the asserted unexpected effects of the claimed invention, upon further consideration of the data in the disclosure, it is seen that the following inventive compounds (first three compounds), and the comparative compound (the last of the four, also corresponds to Example 3 of Bueschel) have stabilization properties shown below [0531]-[0532]:
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That is, the stabilization by the first two inventive compounds and that by the comparative compound (which is within the scope of Beuschel) are all comparable or marginally different and may be within the experimental error. In addition, stabilization by the third inventive compound above is inferior to the last comparative compound. Therefore, the arguments on unexpected effect lack clarity. Applicant is advised provide clarification and an analysis of the scope of the unexpected results in light of the amended claims.
Conclusion
Any inquiry concerning this communication or earlier communications from the
examiner should be directed to Satya Sastri at (571) 272 1112. The examiner can be reached Monday-Friday, 9AM-5.30PM (EST). If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Mr. Robert Jones can be reached at (571)-270-7733. The fax phone number for the organization where this application or proceeding is assigned is (571) 273 8300.
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/Satya B Sastri/
Primary Examiner, Art Unit 1762
Prosecution Insights