DETAILED ACTION
Response to Amendments
In response to the amendment received on 12/02/2025:
• Claims 1-15 are currently pending. Claim 15 is withdrawn for being directed to a non-elected invention(s). The objection to claim 1 is withdrawn in light of the amendments to the claims. The rejection of claims 1-14 under 35 U.S.C. 112(b) are withdrawn in light of the amendments to the claims.
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 text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1-8 and 10 are rejected under 35 U.S.C. 103 as being unpatentable over Ortalano et al. (US-20150252201-A1) (hereinafter referred to as “Ortalano”) in view of Zhenova et al. (Zhenova, Anna, et al. “Solvent applications of short-chain oxymethylene dimethyl ether oligomers.” ACS Sustainable Chemistry & Engineering, vol. 7, no. 17, 29 July 2019, pp. 14834–14840, https://doi.org/10.1021/acssuschemeng.9b02895) (hereinafter referred to as “Zhenova”) and Cai et al. (US-20220112148-A1) (hereinafter referred to as “Cai”), with evidence from Kulbaba et al. (US-20200270437-A1) (hereinafter referred to as “Kulbaba”) as to the rejection of claim 2 only.
Regarding claim 1, Ortalano teaches an offset printing ink composition or an offset varnish composition (see Ortalano at para. 0003, teaching a pigment dispersion for offset printing applications), each composition containing:
• a binder component and a solvent component (see Ortalano at para. 0034, teaching the pigment dispersion as containing a binder and a solvent).
While Ortalano teaches the ink outlined above, Ortalano fails to explicitly teach the solvent component of each composition as comprising at least one oxymethylene ether according to the general formula (1): CH3[OCH2]nOCH3, wherein n is an integer of 2 to 7.
However, Zhenova teaches oxymethylene dimethyl ethers (OMEs) as solvents, where n ranges from 3-5 (see Zhenova at Abstract). Zhenova further teaches the OMEs as being bio-derived, as being cost competitive with traditional solvents, as not being mutagenic nor genotoxic, and to be broadly miscible with organic solvents (see Zhenova at Abstract, pg. 14836, left column, para. 1; pg. 14836, right column, para. 4; and pg. 14839, left column, para. 3). Moreover, Zhenova teaches OMEs as sufficiently dissolving polystyrene polymers (see Zhenova at pg. 14838, right column, last paragraph).
In general, polyoxymethylene dimethyl ethers with n ranging from 3-8 are known to suitably be used as solvents for inks (see Cai at para. 0003).
Ortalano teaches their organic solvent liquid carrier may include non-aqueous solvents, such as ethers (see Ortalano at para. 0050). Moreover, Ortalano teaches polystyrene as a suitable binder (see Ortalano at para. 0044).
Therefore, it would have been obvious for one of ordinary skill in the art before the effective filing date of the claimed invention to use an OME3-5 solvent as an ether solvent in the pigment dispersion of Ortalano. One of ordinary skill in the art would have been motivated to do so in order to use a bio-derived (i.e., green) solvent, to use a solvent that is cost competitive with traditional solvents, to use a solvent that is not mutagenic or genotoxic, to use a solvent that is broadly miscible with a multitude of organic solvents, and to use a solvent that easily dissolves a polystyrene polymer (see Zhenova at Abstract, pg. 14836, left column, para. 1; pg. 14836, right column, para. 4; pg. 14839, left column, para. 3; and pg. 14838, right column, last paragraph).
Following the above modification, the solvent component (i.e., liquid carrier) of Ortalano contains an OME3-5 solvent, which meets the claimed general formula (1).
Regarding claim 2, OME5, where n is equal to 5, has a boiling point of 242 °C, as evidenced by Kulbaba at para. 0079. This value falls within the claimed range. It is noted that while Kulbaba does not specify the temperature at which the boiling point is measured at, absent any indication, one of ordinary skill would readily assume the measurement as being performed at room temperature, which is considered by the Examiner to be close enough to the claimed 23°C value to result in the boiling point limitation to be met.
Regarding claim 3, OME5, which is one of the OME3-5 solvents taught by Zhenova, contains 6 oxygen atoms, 7 carbon atoms, and 16 hydrogen atoms, for a total molecular weight of 196 g/mol (6 • 16 + 7 • 12 + 16 • 1 = 196 g/mol); thus, modified Ortalano teaches embodiments in which the oxymethylene dimethyl ether solvent meets the claimed molecular weight range.
Regarding claims 4-5, see Ortalano at para. 0051, teaching the pigment dispersion as containing less than 80 wt% of the solvent; also see Ortalano at para. 0069, teaching the content of the pigment dispersion in the entire ink may range from 20 to 60 wt%; thus, the content of the solvent in the ink necessarily is 48 wt% or less (60% pigment dispersion maximum • 0.8 ratio of solvent in pigment dispersion = 48% solvent in ink maximum); this range of 48 wt% or less overlaps the claimed range of 5 to 90 wt%, establishing a prima facie case of obviousness, see MPEP § 2144.05; also see Ortalano at para. 0050, teaching a single liquid carrier may be used in their ink; thus, Ortalano necessarily suggests embodiments in which the liquid carrier contains 100 wt% of the oxymethylene ether solvent (i.e., the solvent is used alone), which falls within the claimed range of 20% by weight or greater; additionally, since 100 wt% of the solvent component is the oxymethylene ether solvent, the solvent component necessarily “consists of” the oxymethylene ether solvent.
Regarding claim 6, while Ortalano as modified by Zhenova and Cai teaches the ink outlined above, modified Ortalano fails to teach the solvent component as comprising 20 to 95% by weight of at least one oxymethylene ether according to formula (1) and the remainder to 100% by weight of one or more solvents being selected from the group consisting of mineral oils, vegetable oils, fatty acid esters being different from vegetable oils, alcohols, esters, ethers, glycols, cyclic or linear hydrocarbons, ketones, lactones, alkanes, aromatic hydrocarbons, aromatic compounds and arbitrary combinations of two or more of the aforementioned solvents.
However, Ortalano teaches their liquid carrier may be used as a mixture of one or more liquid carriers, and further teaches ethers and esters as suitable liquid carriers (see Ortalano at para. 0050).
Therefore, it would have been obvious for one of ordinary skill in the art before the effective filing date of the claimed invention to use an ether solvent, such as the OME3-5 solvent, together with an ester solvent as the liquid carrier in the composition of modified Ortalano, as modifed Ortalano teaches both ethers and esters as suitable liquid carriers and further teaches that two or more liquid carriers may be used in combination (see Ortalano at para. 0050). Combining two or more materials disclosed by the prior art for the same purpose to form a third material that is to be used for the same purpose has been held to be a prima facie case of obviousness. See In re Kerkhoven, 626 F.2d 846, 850, 205 USPQ 1069, 1072 (CCPA 1980). See MPEP § 2144.06.
In this case, Ortalano fails to provide explicit guidance as to the ratio of the two or more liquid carriers when used in combination; however, in general, it would have been common sense that when faced with a mixture that is undefined, one of ordinary skill in the art would be motivated to select a 1:1 ratio, absent any teaching to do otherwise. The MPEP supports the position that a patent examiner may rely on "common knowledge and common sense of [a] person of ordinary skill in the art without any specific hint or suggestion in a particular reference.” See MPEP § 2143(I)(E).
Therefore, it would have been obvious for one of ordinary skill in the art before the effective filing date of the claimed invention to set the ratio of the OME3-5 ether liquid carrier to the ester liquid carrier in the composition of Ortalano to be 50:50, since a 1:1 ratio is the most common starting point when mixing two components.
Following the above modifications, the liquid carrier (i.e., solvent) component of Ortalano contains 50% of the oxymethylene ether of formula (1) and 50% of the ester. These values fall completely within the respective claimed ranges.
Regarding claim 7, see Ortalano at para. 0044, teaching the binder may be a polystyrene; also see Ortalano at para. 0047, teaching the content of the binder in the pigment dispersion to range from 1 to 25 wt%; also see Ortalano at para. 0069, teaching the content of the pigment dispersion in the entire ink may range from 20 to 60 wt%; thus, the content of the binder in the ink necessarily ranges from 0.2 to 15 wt% (20% pigment dispersion minimum • 0.01 ratio minimum of binder in pigment dispersion = 0.2% binder in ink minimum; 60% pigment dispersion maximum • 0.25 ratio maximum of binder in pigment dispersion = 15% binder in ink maximum); this range of 0.2 to 15 wt% overlaps the claimed range of 10 to 70 wt%, establishing a prima facie case of obviousness, see MPEP § 2144.05.
Regarding claim 8, see Ortalano at para. 0034, teaching the pigment dispersion to contain a pigment as a colorant; also see Ortalano at para. 0040, teaching the content of the colorant in the pigment dispersion to be less than 80 wt%; also see Ortalano at para. 0069, teaching the content of the pigment dispersion in the entire ink may range from 20 to 60 wt%; thus, the content of the colorant in the ink necessarily is 48 wt% or less (60% pigment dispersion maximum • 0.8 ratio of pigment in pigment dispersion = 48% pigment in ink maximum); this range of 48 wt% or less overlaps the claimed range of 1 to 50 wt%, establishing a prima facie case of obviousness, see MPEP § 2144.05.
Regarding claim 10, see claim 1 analysis above, showing modified Ortalano as teaching the presence of an OME3-5 solvent, which includes an OME solvent where n is equal to 5; also see Ortalano at para. 0050, teaching a single liquid carrier may be used in their ink; thus, Ortalano necessarily suggests embodiments in which the liquid carrier contains 100 wt% of the oxymethylene ether solvent (i.e., the solvent is used alone), which falls within the claimed range of 80% by weight or greater; additionally, since 100 wt% of the solvent component is the oxymethylene ether solvent, the solvent component necessarily “consists of” the oxymethylene ether solvent.
Allowable Subject Matter
Claims 9 and 11-14 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter:
With respect to claims 9 and 12, the prior art fails to teach or suggest an offset printing ink composition or offset varnish composition containing a binder component and a solvent component, wherein the solvent component comprises at least one oxymethylene ether, wherein the solvent component comprises as oxymethylene ether at least one oxymethylene ether according to the general formula (1): CH3[OCH2]nOCH3, wherein n is an integer of 2 to 7, wherein the solvent component comprises 60 to 99% by weight of at least one oxymethylene ether according to formula (1) and remainder to 100% by weight of one or more solvents being different from oxymethylene ether, wherein the at least one oxymethylene ether according to formula (1) comprises at least 60% by weight of one or more oxymethylene ethers each having the general formula (I), wherein n is an integer of 5 to 7 (or 2 to 4, regarding claim 12).
The closest prior art includes Ortalano (US-20150252201-A1) in view of Zhenova (Zhenova, Anna, et al. “Solvent applications of short-chain oxymethylene dimethyl ether oligomers.” ACS Sustainable Chemistry & Engineering, vol. 7, no. 17, 29 July 2019, pp. 14834–14840, https://doi.org/10.1021/acssuschemeng.9b02895) and Cai (US-20220112148-A1). While modified Ortalano teaches most of the limitations as claimed (see claim 1 analysis above), modified Ortalano fails to explicitly teach the solvent component as comprising 60 to 99% by weight of at least one oxymethylene ether according to formula (1) and remainder to 100% by weight of one or more solvents being different from oxymethylene ether, wherein the at least one oxymethylene ether according to formula (1) comprises at least 60% by weight of one or more oxymethylene ethers each having the general formula (I), wherein n is an integer of 5 to 7 (or 2 to 4, regarding claim 12).
While Ortalano teaches the liquid carrier may be used in combinations of two or more (see Ortalano at para. 0050), Ortalano fails to explicitly teach the exact content ratio when two or more liquid carriers are present in the ink composition. There is no teaching or suggestion in the art to set the content of the OME3-5 solvent to fall outside a conventional 50/50 range, like claimed. Further, the prior art fails to teach or suggest the optimization of such a ratio within an ink composition, with there being no indication as to the variables impacted by such an adjustment. Consequently, claims 9 and 12 would be allowed if re-written to be in independent form.
Dependent claims 11, 13, and 14 would also be allowable (if re-written to be in independent form) for the same reasons given above.
Response to Arguments
Applicant's arguments filed 12/02/2025 have been fully considered but they are not persuasive for at least the reasons set forth below.
Applicants argue Zhenova teaches that oxymethylene dimethyl ethers are suitable for the removal of inks and coatings, and that thus, Zhenova discourages and teaches away from the use of that solvent in an ink composition, because that solvent is known to destroy or remove inks (see Applicant’s Remarks at pg. 4). Applicants further argue that nowhere does Zhenova teach the use of oxymethylene dimethyl ethers for a printing ink or varnish (see Applicant’s Remarks at pg. 4).
However, this is not found to be persuasive and so the Examiner must respectfully disagree for the following reasons.
Paint stripping and ink solvation are two sides of the same coin, namely, dissolving capacity. One of ordinary skill in the art would readily recognize the solvent’s ability to dissolve polystyrene (which in Zhenova is framed in the context of paint stripping) to support the compatibility of the solvent with the polystyrene binder taught by Ortalano (in the context as a solvent in an ink composition). Further, one of ordinary skill would readily recognize that the specific requirements of a solvent’s use in a paint stripper—which includes distinct modes of application, drying times, and concentration—would not necessarily render the solvent unsuitable for use in a printing ink context. In fact, one of ordinary skill would have a reasonable expectation of success in using the claimed solvents in an ink, given Cai explicitly teaches the use of the claimed solvent(s) in ink compositions to be known (see Cai at para. 0003). Consequently, Zhenova’s teachings do not teach away or discourage from the use of the claimed solvent in an ink composition, and in fact, one would be motivated to use the claimed solvent to obtain benefits related to toxicity, cost, and dissolving capability of polystyrene (see claim 1 rejection above).
Additionally, it is known that paint-stripping solvents may be suitably used in ink compositions. For example, see US-20120048297-A1 at para. 0006 and 0046, teaching N-methyl-2-pyrrolidone as a known paint-stripping solvent. N-methyl-2-pyrrolidone is a common solvent used in ink compositions, e.g., see Ortalano at para. 0056. Accordingly, one of ordinary skill would not necessarily be discouraged or taught away from using the solvents taught by Zhenova in an ink, given that solvents are routinely known to be interchangeable between the two contexts (paint stripping compositions and ink compositions).
Next, Applicants argue Cai does not teach polyoxymethylene dimethyl ethers as solvents for use in a printing ink or varnish (see Applicant’s Remarks at pg. 5).
However, this is not found to be persuasive and so the Examiner must respectfully disagree for the following reasons.
Cai explicitly teaches the solvents may be “applied in paints, coatings, inks, adhesives…and so on.” Thus, Cai necessarily teaches the solvents may be used in ink compositions. One of ordinary skill would recognize that “inks” as a broad category may include printing inks and offset inks as well. Accordingly, one of ordinary skill in the art would have a reasonable expectation of success in using such solvents in an ink composition like that taught by Ortalano to obtain the benefits taught by Zhenova (see claim 1 rejection above).
Next, Applicant’s briefly suggest Cai may not be prior art given its publication date of April 14th, 2022 (see Applicant’s Remarks at pg. 5). However, Cai has a foreign priority date of September 19th, 2019. Accordingly, Cai has an effective filing date of September 19th, 2019. This date of September 19th, 2019 is before Applicant’s effective filing date of December 6th, 2019. Thus, Cai is properly applied as prior art under 35 U.S.C. 102(a)(2).
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure:
Adami (US-20120048297-A1) teach a paint stripping composition (see Adami at Abstract).
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 extension fee 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 Jeffrey E Barzach whose telephone number is (571)272-8735. The examiner can normally be reached Monday - Friday; 8 am - 5 pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Amber R Orlando can be reached on 571-270-3149. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/J.E.B./
Examiner, Art Unit 1731
/AMBER R ORLANDO/Supervisory Patent Examiner, Art Unit 1731