Notice of Pre-AIA or AIA Status
The present application is being examined under the pre-AIA first to invent provisions.
DETAILED OFFICE ACTION
This Office Action is in response to the papers filed on 17 March 2026.
CLAIMS UNDER EXAMINATION
Claims 1-27 and 30-32 are pending and have been examined on their merits.
PRIORITY
Claim 1 has been amended to recite a non-polar compound is present between 0.1 and 99%. The claim has benefit to Provisional Application 61/852243, filed on 15 March 2013.
WITHDRAWN REJECTIONS
The rejection of claims 1-27 and 30-32 under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, has been withdrawn due to claim amendment.
The rejection of claims 1-27 and 30-32 under pre-AIA 35 U.S.C. 103(a) as being unpatentable over Bromley et al. (2015) has been withdrawn due to claim amendment and benefit of the 2013 priority date.
The rejection of claims 1-28 and 30-32 on the ground of nonstatutory obviousness-type double patenting as being unpatentable over claims 1-2, 5, 8, 10, 13-5, 17, 21-22 and 25 of US Patent 9861611 (09 January 2018) is withdrawn. The terminal disclaimer filed on 17 March 2026 has been approved.
The rejection of claim 28 is now moot due to cancellation.
NEW GROUNDS OF REJECTION
Independent claim 1 has been amended to recite a range of “0.1% and 99%” non-polar compound. The claim previously recited “about 0.1% and 99%”. The amendment recited in claim 1 now has benefit to the 15 March 2013 priority date. The previous rejection has been withdrawn (Bromley 2015 in view of Baogen). New grounds of rejection have been necessitated by claim amendment.
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 1-27 and 30-32 are rejected under pre-AIA 35 U.S.C. 103(a) as being unpatentable over Bromley et al. (Compositions containing non-polar compounds. US 2009/0297665) in view of Baogen et al. (previously cited; Method for separating vitamin E polyethylene glycol succinate monoester from vitamin E polyethylene glycol succinate diester. CN101721838A 2009).
Bromley teaches compositions for preparing foods and beverages that contain additives (Abstract). Bromley teaches a composition containing non-polar active ingredients, water, tocopherol polyethylene glycol succinate (TPGS; a surfactant) and a preservative (see Table 2Ai). The art identifies TPGS as a “polyalkylene glycol derivative of vitamin E” [0016]). The art teaches any known TPGS can be used ([0402]). The art identifies TPGS 400 as a derivative which can be used. Bromley teaches the amount of non-polar compound in the concentrate is between 5% and 10% by weight (w/w) ([0010]).
Bromley teaches a composition comprising:
a water-soluble vitamin E derivative; and
5-10% non-polar compound.
The art is silent regarding the presence of monomers and dimers in TPGS.
Baogen et al. disclose a Tocopheryl Polyethylene Glycol Succinate (TGPS) ester mixture comprising TPGS monoesters and diesters (See Description, page 1, first paragraph). Baogen discloses the TPGS sold on the market (hence, commercially available) is also a mixture of monoester (hence, a monomer) and diester (hence, dimer) components (page 2, second paragraph). Therefore Baogen teaches a water-soluble vitamin E derivative mixture.
Embodiment 3 of Baogen teaches TPGS-400 comprising 55.1% monoester (monomer) and 44.6% diester (dimer). These amounts read on the claimed ranges of monomer and dimer. A mixture containing 55.1% monomer and 44.6% dimer amounts to a total of 99.7%. Therefore Baogen teaches the monomer and dimer together comprise at least 70% by weight of the TPGS 1000 mixture. The art reads on a high dimer mixture.
It would have been obvious to combine the teachings of the prior art by using the Vitamin E derivative high dimer mixture taught by Baogen in the composition disclosed by Bromley. One would have been motivated to do so since Bromley teaches the use of a commercially available TPGS and Baogen discloses a TPGS comprising 55.1% monomer and 44.6% dimer. KSR Rationale A indicates that it is scientifically rational to combine prior art elements according to known methods to yield predictable results, when all of the claimed elements were known in the prior art and one skilled in the art could have combined the element as claimed by known methods with no change in their respective functions, and the combination would have yielded predictable. One would have had a reasonable expectation of success since Bromley teaches the PEG used in the tocopherol-PEG derivative can be any of a plurality of known PEG moieties and Baogen discloses TPGS 400 comprises between 55.1% monomer and 44.6% dimer. One would use a Vitamin E derivative mixture with at least 70% monomer and dimer since Baogen teaches a Vitamin E derivative mixture comprising at least 70% monomer and dimer. One would have expected similar results since both references are directed to the same vitamin E derivative. Claim 1 recites “whereby the high-dimer mixture improves the solubility of the non-polar compound(s) in the composition compared to mixtures that are not high-dimer mixtures”. Because Baogen teaches a water-soluble vitamin E derivative mixture comprising the claimed amount of monomer and dimer, it would be expected to improve as recited in claim 1. Therefore claim 1 is rendered obvious.
Bromley teaches water (supra). Water reads on claims 2-5.
Bromley teaches tocopherol polyethylene glycol succinate (supra). TPGS reads on claims 6 and 9.
Regarding claims 7-8: The art teaches TPGS-1000. As evidenced by the PG Pub of the PEG moiety of TPGS has a molecular weight of 1000 Da. Therefore claims 7-8 are rejected.
Bromley teaches D-α TPGS ([0412]). Therefore claim 10 is included in this rejection.
Regarding claim 11: The art teaches TPGS-1000 ([0402]). Claim 11 is rejected.
Baogen teaches 55.1% monomer (supra). MPEP 2144.05(I) teaches “a prima facie case of obviousness exists where the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have the same properties. Titanium Metals Corp. of America v. Banner, 778 F.2d 775, 227 USPQ 773 (Fed. Cir. 1985).” Claim 12 is rendered obvious.
Baogen teaches 44.6% dimer and 55.1% monomer. Claim 13 is included in this rejection.
Bromley teaches the amount of polar solvent in the concentrate is between 60% and 79% by weight (w/w) ([0014]). This reads on claims 14 and 18.
The amount of surfactant in the composition is between 16% and 30% by weight ([0012]). Claims 15-17 are included in this rejection.
Bromley teaches the amount of non-polar compound in the concentrate is between 5% and 10% by weight (w/w) ([0010]). Claims 19-20 are included in this rejection.
Table 2A(i) (supra) discloses a fish oil. This reads on claims 21-22. EPA is a well known omega-3 fatty acid. Claim 23 is rejected.
Bromley teaches the composition can be used to prepare beverages ([0004] [0006]). The art teaches beverages into which the composition is diluted ([0007] [0063]).This reads on the composition rendered obvious by claim 1, and a beverage base. Therefore claim 24 is included in this rejection. The art teaches fruit juice ([0223]). Claims 25-26 are included in this rejection.
Table 2A(i) (supra) discloses citric acid (an acid). Therefore claim 27 is included in this rejection.
Baogen teaches 44.6% dimer (supra). Claim 30 is included in this rejection.
Embodiment 3 of Baogen teaches TPGS-400 comprising 55.1% monoester (monomer) and 44.6% diester (dimer). These amounts read on the claimed ranges of monomer and dimer. A mixture containing 55.1% monomer and 44.6% dimer amounts to a total of 99.7%. Claim 31 is included in this rejection.
Bromley teaches the amount of non-polar compound in the concentrate is between 5% and 10% by weight (w/w) ([0010]). Therefore claim 32 is included in this rejection.
Therefore Applicant’s Invention is rendered obvious as claimed.
EXAMINER’S RESPONSE TO APPLICANT’S ARGUMENTS
The arguments made in the response filed on 17 March 2026 are acknowledged.
The Applicant directs Examiner to the previous arguments filed in the instant Application.
The Applicant argues Bromley does not mention a mixture of TPGS monomer and a high amount of dimer compared to the standard surfactant, such as Eastman TPGS used in the example in Bromley. The Applicant argues the TPGS sold by Eastman does not contain the claimed amount of dimer.
In response: The rejection above acknowledges Bromley is silent regarding the presence of monomer and dimer in the disclosed TPGS. Bromley does not require the use of Eastman TPGS. Bromley teaches “any known source of TPGS can be used” ([0179]). Claim 1 encompasses any polyalkylene glycol derivative of Vitamin E. The rejection relies on the TPGS 400 taught by Baogen, which contains the claimed amounts of monomer and dimer. Therefore the argument is not persuasive.
Arguments: The Applicant argues Baogen does not teach replacing the vitamin E source of Bromley with a high dimer mixture. The arguments state Baogen discloses two examples the comprise the claimed amounts of monomer and dimer. The Applicant argues Baogen does not teach these TPGS mixtures have improved solubilization properties.
The Applicant argues none of the references disclose dimer vitamin E derivative mixtures improve the solubility of non-polar compounds compared to compositions comprising TPGS that do not contain a high dimer mixture.
The Applicant states Baogen teaches commercially available TPGS contains diester only as a side product. The Applicant refers to a side product as “an impurity”.
The Applicant alleges Baogen teaches that any dimers present in commercially available TPGS are an undesired byproduct, in relatively low concentrations. The Applicant argues Baogen does not teach using the raw material as a surfactant, but describes that TPGS surfactant is the monoester form.
The Applicant asserts Baogen does not teach compositions containing non-polar compounds and high dimer mixtures of a vitamin E derivative (such as TPGS), nor the use of high dimer mixtures for preparing emulsions or pre-emulsion concentrates.
In response: Contrary to the Applicant’s arguments, Baogen teaches three embodiments comprising TPGS compounds comprising the claimed amounts of monomer and dimer: Example 3 (TPGS 400). The rejection relies on the teachings of Bromley in view of Baogen. Bromley teaches the use of any TPGS, including TPGS 400 ([0178]). Baogen is relied upon because it teaches a TPGS 400 mixture comprising amounts of monomer and dimer that read on the claimed amounts. Because Baogen teaches a water-soluble vitamin E derivative mixture comprising the claimed amount of monomer and dimer, it would be expected to produce a composition with the claimed characteristics.
The following is noted from the Baogen reference (see page 2, second paragraph):
However, the existing commodity TPGS on the market does not give a detailed description of its ingredients and content, mainly because it has certain difficulties in separation as a polymer. The composition of the product obtained after the reaction of vitamin E succinate with polyethylene glycol is very complex. In addition to the polymer itself having a certain distribution in molecular weight, there is also a side reaction product-vitamin E polyethylene glycol succinic acid Diester. The two differ in structure by only one vitamin E succinate functional group, coupled with a more complex molecular weight distribution, so separation is not easy. The commercial TPGS sold on the market, because of the mixture of diesters, the purity of the monoester is not high, only about 80%. The purity of monoester directly affects the effect of TPGS as a surfactant and another form of vitamin E supplementation. In many literatures, it is not mentioned that TPGS is completely separated before use. In this case, some effects of TPGS obtained are inaccurate. As another product obtained by the reaction, diesters are difficult to completely separate from monoesters. Therefore, the role of diesters and their differences from monoesters have not been well studied. Therefore, it is of great significance to separate and purify the vitamin E succinate and the mixture of polyethylene glycol reaction products.
The art teaches the TPGS on the market does not give a detailed description because the components are difficult to separate. The art teaches diester is difficult to separate from the monoester. Baogen teaches the purity of monoester affects the effect of TPGS when used as a surfactant. Baogen teaches the role of diesters and their differences from monoesters have not been well studied. Therefore, it is of great significance to separate and purify the vitamin E succinate and the mixture of polyethylene glycol reaction products.
The Examples disclosed by Baogen analyze TPGS compounds to determine the amounts of monoester (monomer) and diester (dimer) present. Baogen never refers to the diester as a “contaminant” as alleged by the Applicant. Examiner notes Baogen teaches “the TPGS mixture contains TPGS monoesters, diesters and a small amount of impurities” (see page 5, first sentence of the section titled “Separation Step”). Therefore Baogen never refers to diesters as impurities. Baogen refers to components other than monoesters and diesters as “impurities”. Baogen uses a “sample” of TPGS 1000 as a raw material for chromatographic analysis. Baogen does so because the reference teaches the components TPGS on the market have not been well studied.
Arguments: The Applicant alleges “Baogen et al. teaches that it is useful to separate and purify the monoester and diester components of the impure TPGS raw material prior to use of the monoester, for example, as a surfactant”. Examiner notes this is not stated in Baogen. Baogen teaches TPGS on the market does not give a detailed description of its ingredients and content. Baogen teaches the purity of monoester directly “affects the effect” of TPGS as a surfactant and another form of Vitamin E supplementation. While Baogen teaches the amount of monoester affects the effect as a surfactant and Vitamin E supplement, Examiner notes the art does not teach it cannot be used for Vitamin E supplementation.
The Applicant asserts Baogen cannot and does not teach compositions containing non-polar compounds and high dimer mixtures of a vitamin E derivative (such as TPGS), nor the use of high dimer mixtures for preparing emulsions or pre-emulsion concentrates. Examiner notes claim 28 does not recite an emulsion or a pre-emulsion concentrate. Therefore the arguments are not persuasive.
The Applicant argues the claimed invention has unexpected properties. The Applicant argues the advantageous properties are pronounced when dimer is present in the mixture at an amount between 29% and 69%. The Applicant states the instant application demonstrates that the solubilization properties of the polyalkylene glycol derivative of vitamin E mixtures increases as the amount of dimer form in the vitamin E derivative mixture increases, and that “this property is most pronounced when there is between about 29% and 69% dimer form in the vitamin E derivative mixture”. The Applicant refers to Example 9 of the instant specification, which uses TPGS from Eastman Chemical Company containing 11% dimer and 86% monomer.
In response: Examiner points out the experiments disclosed in the specification use TPGS from Eastman Chemical Company containing “~11%” dimer and “~86%” monomer. The rejection is not based on the use of Eastman Chemical Company’s TPGS.
The Applicant points to Example 1 of the specification and argues the advantageous properties are pronounced when dimer is present in the mixture at an amount between 29% and 69%. Examiner notes Example 1 discloses monomer between 39.35% and 60% and dimer between 29.27% and 54.90%. It is not commensurate with the scope of claim 28.
The Applicant states the instant application describes that its dimer and monomer mixture of vitamin E derivatives is prepared in such a way that increased dimer formation is favored in the mixture. The intentional mixing of two components is the opposite of the separation of two components.
In response, Examiner notes the claims are not directed to a method of making a high dimer mixture. The claims recite a high dimer mixture comprising the claimed ranges of monomer and dimer. The arguments are not persuasive.
CONCLUSION
No Claims Are Allowed
Applicant's amendment necessitated the new 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 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 date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to NATALIE MOSS whose telephone number is (571) 270-7439. The examiner can normally be reached on Monday-Friday, 8am-5pm EST.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Sharmila Landau can be reached on (571) 272-0614. The fax phone number for the organization where this application or proceeding is assigned is (571) 273-8300.
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/NATALIE M MOSS/ Examiner, Art Unit 1653
/SHARMILA G LANDAU/Supervisory Patent Examiner, Art Unit 1653
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