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 .
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.
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.
Claims 33-41 and 43-46 are rejected under 35 U.S.C. 103 as being unpatentable over Roeger-Goepfert et al. US 9,011,666 B2 and in view of Grove et al. US 2018/0201733 A1.
Roeger-Goepfert discloses a leveling agent composition derived from alkoxylated polyalkanolamine for metal electroplating (col 2, lines 25-28).
Reference Grove teaches a quick-setting polymeric coating composition derived from amine and epoxy compounds (title and abstract), used to coat a metal surface (para [0052]).
Regarding claim 33, Roeger-Goepfert teaches (reference claims 1 and 3), a leveling agent which is obtained by condensing a trialkanolamine of formula (1a) N(R1-OH)3 , to obtain a polyalkanolamine (II). Roeger-Goepfert further discloses alkoxylation of the polyalkanolamine (II) with either a C2-C12 alkylene oxide or glycidyl ether. Roeger-Goepfert discloses (col 16, Example 1) condensation of triethanolamine (corresponding to formula (I), where A1, A2, A3 are linear C1 alkylene, where R1, R1*, R2, R2* are H, and where R3 is # -C(R4 R4*OH), where R4 and R4* are H, and where the resulting leveling agent polytriethanolamine, has a hydroxy number of 611.5 mg KOH/g, which corresponds to applicant’s required intermediate Q.
Roeger-Goepfert further utilizes the generated polytriethanolamine of Example 1 in an alkoxylation reaction (col 17, Example 6) where the moles of hydroxy groups of polytriethanolamine, corresponding to intermediate Q = (611.5/56,100) moles/g x 202.1g=2.2 moles, and which is reacted with 128 g of propylene oxide = 128/58.08 =2.2 moles; resulting in the ratio of moles of hydroxy-group of intermediate Q to moles of propylene oxide of 1:1. Per Roeger-Goepfert’s disclosure (claim 3), it would be obvious to have utilized a glycidyl ether instead of propylene oxide in Example 6. Roeger-Goepfert’s only indicates glycidyl tert-butyl ether as an example of glycidyl ethers (col 7, line 66), but does not limit the use of other glycidyl ethers conforming with Formula (II).
Reference Grove who also teaches closely related polymer adducts to Roeger-Goepfert’s alkoxylated polyalkanolamine, recognizes the equivalence of t-butyl glycidyl ether and 2-ethyl hexyl glycidyl ether (para [0038]), where 2-ethyl hexyl glycidyl ether corresponds to the required glycidyl ether of formula (II), were R9 is a branched octyl.
Since it is prima facie obvious to substitute art recognized equivalents known for the same purpose (MPEP 2144.06 II). An obvious polymer composition P derived from the teaching of Roeger-Goepfert in view of Grove would be wherein Example 6 (as discussed above), 2.2 moles of propylene oxide is substituted with 2.2 moles of 2-ethyl hexyl glycidyl ether (409.9g) and reacted with 2.2 moles of hydroxy groups of polytriethanolamine (202.1g), to obtain an alkoxylated polytriethanolamine corresponding to polymer P. The ratio of moles of hydroxy-group of intermediate Q to moles of 2-ethyl hexyl glycidyl ether corresponding to formula (II) would still be 1:1, and the amount of triethanolamine of formula (I) would be 202.1/(202.1 +409.9) x 100 ≈ 33 wt% and the 2-ethyl hexyl glycidyl ether of formula (II) would be 67 wt%, based on the total weight of polymer P.
It would have been obvious to one of ordinary skilled in the art before the effective filing date of the invention to have substituted propylene oxide in Roeger-Goepfert with the 2-ethyl hexyl glycidyl ether as taught by Grove for the same application of creating a polymeric leveling agent.
Regarding claims 34-38, 40-41 and 45, as discussed when addressing claim 33, Roeger-Goepfert discloses (col 16, Example 1) condensation of triethanolamine (corresponding to 100% of formula (Ia)), where A1, A2, A3 are methylene, where R1, R1*, R2, R2* are H, and where R3 is # -C(R4 R4*OH), where R4 and R4* are H.
Regarding claims 39 and 46, Roeger-Goepfert discloses (col 21, reference claim 10) triisopropanolamine, making the claimed requirement obvious.
Regarding claim 43, Roeger-Goepfert is silent on the use of diglycidyl ether, however reference Grove teaches multi-functional epoxy compounds such as propylene glycol diglycidyl ether (Grove para [0037]), which corresponds to Formula (IIa), to manage the molecular weight of the polymeric adduct, to tailor its storage stability and fast setting property (para [0036]).
It would have been obvious to one of ordinary skilled in the art before the effective filing date of the invention to have modified the embodiment of Roeger-Goepfert and Grove, as discussed when addressing claim 1, and utilize propylene glycol diglycidyl ether along with n-hexyl glycidyl ether, as taught by Grove for the same application of creating a polymer adduct with desired molecular weight. An artisan skilled in the art would incorporate small amount of the diglycidyl ether conforming with the claimed requirement in order to prevent polymer gelling.
Regarding claim 44, as discussed when addressing claim 1, condensation of triethanolamine to generate the required intermediate Q is disclosed by Roeger-Goepfert. Reference Grove teaches n-dodecyl glycidyl ether, which corresponds to R9 requirement of dodecyl(Grove para [0038]), thus making the claimed requirement obvious.
Claims 47-48 are rejected under 35 U.S.C. 103 as being unpatentable over Roeger-Goepfert and in view of Grove, as applied to claims 33-46 above, and further in view of Chung et al. US 4,596,842 and European patent application No. 07120393, cited within Roeger-Goepfert (Equivalent reference Misske et al. US 2010/0234631 is utilized for the rejection below).
Regarding claims 47-48, Roeger-Goepfert teaches (reference claim 3) at least one glycidyl ether as an alkoxylating agent, thus implying that more than one glycidyl ether can be utilized as the alkoxylating agent. Both Roeger-Goepfert and Grove are silent on the glycidyl ether conforming with Formula IIp and IIq. Analogous reference Chung also teaches alkanolamine hydroxy-capped epoxy for cathodic electrocoat (title), and teaches monoepoxides such as dodecyl glycidyl ether and tetradecyl glycidyl ether corresponding to Formula IIp and IIq respectively (Chung col 6, line 49). Advantageously, Chung provides the motivation to utilize the monoepoxides to improve the electrical insulating, flexibility and corrosion resistance properties of the coating resin composition (Chung col 6, lines 62-68).
Roeger-Goepfert discloses the condensed triethanolamine (reference claim 10), corresponding to intermediate Q, but does not provide a range of hydroxyl number values of the self-condensed polyalkanolamine in the general disclosure. Roeger-Goepfert however cites European patent application No. 07120393 (col 2, line 6) to provide additional details of the polyalkanolamine. Reference Misske (para [0058]) notes the hydroxyl number of the condensation product, corresponding to intermediate Q, to be 200 to 1500 mg(KOH)/g, which overlap the claimed requirement. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990). In the instant case, in the absence of showing of the criticality of the claimed range and owing to the closeness of the materials disclosed, the overlapping range of the prior art is sufficient to support an obviousness rejection.
As discussed, when addressing claim 1, obvious embodiment of Roeger-Goepfert and Grove utilizes 2-ethyl hexyl glycidyl ether, which corresponds to glycidyl ether Formula IIr.
It would have been obvious to one of ordinary skilled in the art before the effective filing date of the invention to have further modified Roeger-Goepfert and Grove with dodecyl glycidyl ether and tetradecyl glycidyl ether as taught by Chung for the same application of creating a polymer coating composition with improved electrical insulating, flexibility and corrosion resistance properties.
Response to Arguments
Applicant's arguments filed on 07/07/2026 have been fully considered, please see the response below.
Applicant submits that the rejection of claims 33-46 under 35 U.S.C. § 103 over Roeger-Goepfert in view of Grove does not establish that a person of ordinary skill in the art would have selected the presently claimed long-chain R9 residues in the amended range, together with the amended molar ratio, with a reasonable expectation of arriving at the claimed polymer P.
In response, as discussed in the rejection the primary reference Roeger-Goepfert teaches t-butyl glycidyl ether and secondary reference recognizes 2-ethyl hexyl glycidyl ether as equivalents. Both t-butyl glycidyl ether and 2-ethyl hexyl glycidyl ether share close structural similarity and a skilled artisan understands that the compounds similar in structure will have similar properties and thus similar utility, and a person of skill in the art, reading the reference would at once envisage the claimed R9 residue. Additionally, the required molar ratio is achieved by substitution of propylene oxide with identical moles of 2-ethyl hexyl glycidyl ether in the embodiment of Roeger-Goepfert, which would be immediately recognizable option available to one of ordinary skill in the art. Applicant is reminded that “It is prima facie obvious to substitute equivalents, motivated by the reasonable expectation that the respective species will behave in a comparable manner or give comparable results in comparable circumstances. In re Ruff, 256 F.2d 590, 118 USPQ 340 (CCPA 1958). The express suggestion to substitute one equivalent for another need not be present to render the substitution obvious. In re Fout, 675 F.2d 297, 213 USPQ 532 (CCPA 1982).”
Applicant submits that secondary reference Chung utilized to teach dodecyl and tetradecyl glycidyl ethers is non analogous since Chung uses monoepoxides to improve electrical insulating, flexibility, and corrosion- resistance properties of a resin. Applicant adds that Chung’s teaching is directed to a different context than the presently claimed polymers and their use as wetting agents and defoamer components for coating systems, and Chung does not supply a reason to modify the asserted Roeger-Goepfert/Grove combination in the manner required by amended claims 47 and 48.
In response to applicant's argument, Roeger-Goepfert and Grove are useful for surface coating compositions for metals. Reference Chung also teaches coating compositions for metal surfaces. Thus, references Roeger-Goepfert, Grove and Chung belong to the same field of endeavor, which are pertinent to applicant’s compositions where the required polymer P are also used for coating compositions for metal substrate (instant specification page 47, line 20, 35 and page 50, line 9). Chung provides appropriate motivation to utilize the required monoepoxides to improve flexibility and corrosion-resistance properties of a coating resin composition.
Applicant's arguments do not clearly point out the patentable novelty which the claims present in view of the state of the art disclosed by the references cited. Further, they do not show how the amendments avoid such references or objections. Applicant arguments against reference combination of Roeger-Goepfert and Grove (and Chung) are not convincing and the prior art references continue to provide the support for maintaining the rejection of the amended claims.
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.
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/S.M.D./
Examiner, Art Unit 1765
/JOHN M COONEY/Primary Examiner, Art Unit 1765
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