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 Objections
Claim 1 should be revised to include the word “content” or “concentration” after each incidence of the word “group” in the last two lines of the claim. The latter is recommended insofar as it would homogenize the subject matter of claim 1 with that of claim 7.
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.
Claim 9 is 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. The concept of one solvent having “an affinity for” another solvent is imprecise and, hence, merits a rejection under 112(b). If the above phrase means something other than fully miscible with, than Applicant should revise the claim to replace the above phrase with its intended meaning. (The Examiner is only being speculative as to whether or not “an affinity for” is equivalent to “fully miscible with”.)
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 1-13 are rejected under 35 U.S.C. 103 as being unpatentable over the article entitled “An Innovative Approach to Implementation of Organotellurium-mediated Radical Polymerization (TERP) in Emulsion Polymerization” authored by Sugihara et al., and published in Macromolecules (2015) 48, 4312-4318 (hereinafter Sugihara) in view of Umemoto, U.S. Patent Application 2019/0002620.
Sugihara is directed to the preparation of styrene polymers employing organotellurium-mediated radical polymerization in an emulsion environment utilizing a combination of particular surfactant compounds with toluene representing a component of the discontinuous phase in some permutations. The polymer products, like those claimed, will inherently feature tellurium-based moieties at one end of the polymer. The stated benefits of the method are the ability to carry out the emulsion polymerization in a single pot with good colloidal stability being observed and a resulting narrow particle size distribution (abstract).
The Examiner acknowledges, however, that there is no mention of an operation to remove and recover/isolate the tellurium present at the ends of polymer chains upon completion of the polymerization. Umemoto, which also teaches vinyl polymers obtained from organotellurium-mediated polymerization [0065+], states that the presence of tellurium-based end groups causes discoloration of the polymer product and also bestows upon the polymer inadequate thermal stability [0099] thus offering motivation to a practitioner of the invention disclosed in Sugihara to implement some means of removing/replacing the tellurium groups. Among the established ways of doing so identified in that same passage is to react the polymer material bearing reactive tellurium moieties with a reducing agent such as a thiol compound. Tin compounds are mentioned as another possible reducing agent but there are ongoing efforts to restrict the usage of tin compounds, particularly in polymer synthesis/modification where they are not easily removed, due to the documented environmental concerns associated with this class of reactant compounds. (Applicant is also directed to the review article entitled, “Precision Polymer Synthesis by Degenerative Transfer Controlled/Living Radical Polymerization using Organotellurium, Organostibine, an Organobismuthune Chain Transfer Agents” authored by Yamago and published in Chemical Reviews (2009) 109, 5051-5068, and particularly the subject matter under heading 3.5.3 End Group Transformations, where it is established that the usage of thiol compounds is a long-recognized means for replacing tellurium compounds.)
Paragraph [0099] of Umemoto continues to say that the tellurium by-product obtained upon reacting the tellurium group-terminated polymer with a thiol reducing agent is subsequently isolated from the polymer by water/solvent washing or liquid-liquid extraction, which is the operation defined by (ii) in the instantly-claimed method.
There is little further development of the concept of reacting the tellurium group-terminated polymer with a thiol reducing agent by Umemoto. More particularly, there is little guidance on what thiol compounds would be best suited for the subsequent reduction reaction. The Examiner submits though that, to the extent that water constitutes the continuous host medium of the polymerization system disclosed in Sugihara, one of ordinary skill would immediately appreciate that the thiol compound should be one that comprises moieties that render it water-soluble. Indeed, the introduction of a water-insoluble reducing agent to modify the emulsified polymer would result in the reaction being very slow and ultimate conversions low.
In the language of the claims, it is the Examiner’s position that it would be obvious to use a water-soluble thiol compound as the “reactant” to modify the emulsion polymer (polymer particles A) dispersed in water (first solvent) to remove the organotellurium group. This, of course, would yield polymer particles B have a reduced content of polymer chains terminated with said organotellurium moiety. Also, to reiterate, Umemoto also contemplates ways of isolating the organotellurium by-product from the polymer particles B as step (ii) of the claimed method requires.
Concerning claim 2, insofar as the combined teachings of the aforementioned disclosures suggest carrying out the same combination of operations set forth in claim 1, the skilled artisan has a reasonable expectation that the shapes of the particles A would be maintained.
Concerning claim 4, the reducing agent alluded to above, as adapted for the system taught by Sugihara, would contain a thiol moiety reactive with the organotellurium group and another structural attribute that is water-soluble.
As for claim 5, the Examiner takes notice that the second substituents outlined in this claim are among those most often introduced into a compound for which water solubility is necessitated.
Regarding claim 7, a method gleaned from the combined teachings of Sugihara and Umemoto addresses all aspects of the instant invention (with the acknowledged caveat that a water-soluble reducing agent, i.e. soluble in the first solvent, is not specified but nevertheless deemed obvious for reasons detailed supra). Accordingly, one of ordinary skill has at least a reasonable expectation that the particles provided following the reduction reaction will exhibit similarly smaller quantities of tellurium content.
As for claims 9-11, just as Umemoto offered few details as to what is the full scope of reducing agents that are suitable, there is also little guidance offered where appropriate solvents for washing are concerned. What is indisputable, though, is that one of ordinary skill would immediately recognize that the wash, or second, solvent must be one into which the tellurium by-product will be dissolved but the polymer particles will not.
As for claim 12, ultrafiltration is one of the separation techniques contemplated in [0099] for isolating tellurium by-product from the polymer.
Claims 15 and 16 are rejected under 35 U.S.C. 103 as being unpatentable over the article entitled “An Innovative Approach to Implementation of Organotellurium-mediated Radical Polymerization (TERP) in Emulsion Polymerization” authored by Sugihara et al., and published in Macromolecules (2015) 48, 4312-4318 (hereinafter Sugihara) in view of Umemoto, U.S. Patent Application 2019/0002620 as applied to claims 1-13 above, and further in view of the article entitled “Living Ab Initio Emulsion Polymerization of Methyl Methacrylate in Water using a Water-Soluble Organotellurium Chain Transfer Agent under Thermal an Photochemical Conditions authored by Fan et al. and published Angew Chem. Int. Ed. (2018) 57, 962-966.
The particles obtained upon carrying out the polymerization according to the teachings of Sugihara are said to have “narrow” particle size distributions with average diameters below 100 nm, and a molecular weight distribution below 1.3. See the very last passage of the document. Sugihara does not attach a meaning to narrow particle size distributions but Fan characterizes a size distribution of 0.13 as broad on page 963, right column, second full paragraph. (It is not insignificant that both Sugihara and Fan characterize the polymerization approach as TERP reactions in “ab initio emulsion polymerization” systems.) Fan, in the Examiner’s estimation, evidences that one of ordinary skill would, thus, regard a narrow particle size distribution as described by Sugihara as being less than 0.7.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MARC S ZIMMER whose telephone number is (571)272-1096. The examiner can normally be reached M-F 8:30-5:00.
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January 1, 2026
/MARC S ZIMMER/Primary Patent Examiner, Art Unit 1765