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 .
DETAILED ACTION
1. Claims 1-20 are pending in the current application.
2. This application is a CON of PCT/EP2021/072590 08/13/2021 FOREIGN APPLICATIONS EP 20191681.4 08/19/2020.
Response to Restriction Election
3. Applicant’s election of group I in the reply filed on November 20, 2025 is acknowledged. The election was made with traverse and the examiner finds the arguments unpersuasive. The traversal is on the grounds of no search burden. There is a serious search burden given the substantial generic structure and the diverse subject matter. The literature for synthesizing compounds is found in the non-patent literature and patent literature of organic chemistry while that for using crosslinkers and making polymers is found in the polymer literature. It is necessary to search for one of the inventions in a manner that is not likely to result in finding art pertinent to the other invention(s). The compounds must be evaluated for novelty and obviousness independent of their method of making and use and are found in the STN database REGISTRY, disparate chemical catalog space, public chemical databases including but not limited to PUBCHEM, (PubChem is an open chemistry database at the National Institutes of Health (NIH)), CHEMSPIDER (ChemSpider is a free chemical structure database providing fast text and structure search access to over 100 million structures from hundreds of data sources), ZINC (ZINC is a free database of commercially-available compounds for virtual screening. ZINC contains tens of millions of purchasable compounds in ready-to-dock, 3D formats. ZINC is provided by the Irwin and Shoichet Laboratories in the Department of Pharmaceutical Chemistry at the University of California, San Francisco (UCSF)), dissertation databases and repositories around the world (Proquest, DART-Europe, Shodhganga, JAIRO, DiVA, CiNii Dissertations, NARCIS, TESEO, Helveticat, EThOS, Tez Merkezi, RENATI, RCAAP, eLABa ETD, BASE, Deutsche Nationalbibliothek, Tesis Doctorales en Red, Theses France, DOKS, BicTel/e, Trove, Central Asian Thesis Repository, HKUTO) and patent databases maintained by the United States Patent and Trademark Office and patent offices worldwide (ESPACE, WIPO, JPO, KIPO, SIPO). The literature for synthesizing compounds is found in the substantial non-patent literature and patent literature of organic chemistry and specialized reaction databases (CAPLUS, Beilstein, REAXYS, CASREACT, SYNTHLINE, Houben-Weyl’s Science of Synthesis).
It is noted that the election of the genus on page 4-5, species election grouping B, is non-responsive. As explained in the requirement arguing that “all claims are generic is considered nonresponsive unless accompanied by an election.” [Restriction Requirement of September 24, 2025 page 6 at 6. ¶ 3] However, a species election was made of compounds under the heading C on page 5 where R1 is methoxy and R is methoxy, methyl, phenyl or vinyl (Examples 1-4). This is taken as evidence that the species Examples 1-4 are not patentably distinct. [Restriction Requirement of September 24, 2025 page 7 ¶ 1] “In either instance, if the examiner finds one of the species unpatentable over the prior art, the evidence or admission may be used in a rejection under 35 U.S.C. 103(a) of the other species.” No explanation as to which claims read on the elected species was given, which could be held non-responsive, however in the interest of advancing prosecution the examiner has determined which claims read on the elected species. As best as can be understood, the compounds are those of Formula IA claim 2, where R6, R7, and R8 are H, m is 1, X is S, q is 0, R1 is methoxy, n is 2), R4 is alkyl, vinyl or phenyl. According to applicants’ representative claims 1-10, 20 read on the elected species. As detailed in the following rejections, the elected species was not found patentable. The search and examination was continued until prior art was found that anticipated or rendered obvious the elected species that falls within the scope of the generic Markush claim reading on the elected species. As per MPEP 803.02 II. C. “[T]he examiner must continue to search the species of the claim unless the claim has been found to be unpatentable over prior art.” The examiner “need not continue to search the claim if the claim is rejected over prior art”. [ibid. D.] Therefore, the search and examination was not extended unnecessarily and was restricted to the claims reading on the elected species, and claims not reading on the elected species will be held withdrawn.
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.
4. Claim 1-10, 20 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. Claim 1 has R2 defined as H, or various hydrocarbon groups, however only a single bond is present. Assuming the attachment to the hydrocarbon groups was solely through a double bond and this was a substituted vinyl, there is no interpretation of H that makes any chemical sense, as this would require two bonds to hydrogen.
Claim 2 recites the limitation
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in claim 1 there is no provision for the cyclic structure being substituted and no list of the substituents R6-R8. There is insufficient antecedent basis for this limitation in the claim since the cyclic structure does not have substituents.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
5. Claims 2-6 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 1 defines R4 and claim 3 defines R6, R7 and R8 respectively as “a linear or branched, substituted or unsubstituted hydrocarbon group having 1 to 20 caron atoms” however dependent claims, 3-6 define R4, R6, R7 and R8 as cyclic compounds including “C4 to C8 cycloalkyl”, “C6 to C20 aryl,” “C5 to C20 aryl” “C5 to C12 aryl”, phenyl or pyridinyl and groups. The terms ”linear or branched” refer only to alkyl or other noncyclic alkyl compounds and referring and cyclic structures do not fall under either of the descriptions linear or branched. The specification explains that this terminology applies to only alkyl or alkenyl groups as discussed on page 4 at paragraphs [0015] and [0016], respectively. Since claim 1 and 3 do not embrace cyclic structures, the dependent claims are in improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Claim 6 lists R4 as a pyridinyl and according the special definition in the specification on page 4-5 at paragraph [0017] pyridinyl is an aryl group which means in the lexicographical paradigm of this application aryl also includes heteroaryl. Pyridine also lacks antecedent basis and fails to limit claim 1.
Claim 2 recites the limitation
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in claim 1 there is no provision for the cyclic structure being substituted and no list of the substituents R6-R8. Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
6. Claim(s) 1-10, 20 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by George US 2,640,833. George discloses anticipatory compounds including but not limited to
methyl(2-thienyl)dichlorosilane at col. 3 line 45; methyl di-(2-thienyl)chlorosilane at col. 3 lines 59-60; dimethyl(2-thienyl)chlorosilane at col 3. line 72, col. 4 lines 3-4; phenyl(2-thienyl)dichlorosilane at col. 4 line 9; methyl 2-thienyldiethoxysilane, col. 4 lines 29-31; phenyl 2-thienyldiethoxysilane col. 4 lines 33-35; dimethyl 2-thienyl-ethoxysilane col. 4 lines 59-61; and compounds at col. 5 lines 4-27: ethyl 2-thienyl dichlorosilane, ethyl 2-thienyldibromosilane, di propyl 2-thienylchlorosilane, diamyl 2-thienyl chlorosilane, didecyl 2-thienylbromosilane, phenyl 2-thienyldibromosilane, chlorophenyl 2-thienyl dichlorosilane, phenyl 2-(chlorothienyl) dichlorosilane, diphenyl 2-thienylchlorosilane, naphthyldi-(2-thienyl) chlorosilane, phenyl di- (2-thienyl)chlorosilane, benzyl 2-thienyldichlorosilane, tolyl-2-thienyldichlorosilane, vinyl 2-thienyldichlorosilane, allyl-2-thienyldichlorosilane, methyl 2-(methylthienyl)dibromosilane, ethyl-2-thienyldiethoxysilane, ethyl-2-thienyldibutoxysilane, dipropyl-2-thienylpropoxysilane, diamyl 2-thienylethoxysilane, didecyl 2-thienylbutoxysilane, phenyl 2-thienyldibutoxysilane, diphenyl 2-thienylhexoxysilane, naphthyl di-(2-thienyl)ethoxysilane, phenyl di-(2-thienyl)ethoxysilane, benzyl-2-thienyldiethoxysilane, tolyl 2-thienyldiethoxysilane, vinyl 2-thienyldiisobutoxysilane, and allyl 2-thienyldiethoxysilane . These compounds read on claim 2 Formula I-A and claim 1 vis-à-vis claim 2 where R1 is various hydrolysable groups including halogen (Br, Cl) and alkoxy (ethoxy, butoxy, propoxy, hexoxy), which is listed in claim 4, R4 is alkyl (methyl, ethyl, propyl, amyl, benzyl [substituted alkyl or aralkyl]), C5 to C20 aryl (phenyl, tolyl, benzyl, napththyl), C2 to C12 alkyenyl (vinyl, allyl) R6, R7 and R8 are H or methyl, X is S, q is 0, R5 is any definition since q is 0, n is 1 or 2, m is 1 or 2, k is 0 or 1, the sum of n, m and k being 4. The compounds are used in curable compositions, meeting the limitation of claim 9, to make polysiloxanes as discussed at col. 1 lines 32 ff.:
The hydrolyzable thienyl-substituted silanes described above in the foregoing formulas may be employed for rendering materials water repellent which were originally water-non-repellent and may also be used as intermediates in the preparation of thienyl-substituted polysiloxanes.
“Rendering materials water repellent” would involve “end capping” any exposed residues on the surface of materials, meeting the limitation of claim 10. With regard to the claim 20, a product by process claim. By applicants’ admission the elected species and the compounds of claim 1 meet the structural limitations of claim 20. Patentability is based on the product itself, not the method by which it is made. Since the claims are directed to the product of claim 1, and are the same material anticipation is met. See MPEP 2113 for a discussion of Product by Process claims: "[E]ven though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process." The claimed compound having the group R1 that is hydrolysable which makes it inherently moisture curable.
7. Claim(s) 1-10, 20 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by
Khananashvili, L. M.; “Synthesis and properties of thienylorganosilanes and -siloxanes.” International Journal of Polymeric Materials, 1992, 17(3-4), 195-203. Khananashvili discloses anticipatory compounds including but not limited to the compounds of formula RR’SiCl2, and RR’Si(OCOCH3)2 of Formula (I), (III) and (III) on page 197, which read Formula I-A and claim 1 vis-à-vis claim 2 where R1 is various hydrolysable groups including halogen (Cl) and acetoxy, which is listed in claim 4, R4 is alkyl (methyl), C5 to C20 aryl (phenyl), R6, R7 and R8 are H or methyl, X is S, q is 0, R5 is any definition since q is 0, n is 2, m is 1 or 2, k is 0 or 1 the sum of n, m and k being 4. These compounds were part of a curable composition, “Methylthienyldihydroxysilane and a,w-dihydroxymethylthienylsiloxanes were obtained by hydrolysis reaction of methylthienyldichlorosilane and a,w-dichlororomethylthienylsiloxanes at low temperatures in the presence of an acceptor of HCl- aniline.” [Page 197 2nd to last paragraph] Other condensations are described on page 199, “ Thienyl-containing organocyclosiloxanes with different organic radicals at the silicon atom were obtained by the method of heterofunctional condensation.” The condensations are hydrolytic as discussed on page 200, “Thus, hydrolytic condensation of methylthienyldiacetoxysilans was conducted at different temperatures…” and page 203, “Hyrolytic[sic] condensation of thienylmethyldichlorosilanes and diacetoxysilanes yielded, correspondingly, a,w-dihydroxymethylthienylsiloxanes and thienylmethylcyclosiloxanes. By the method of heterofunctional condensation of methylthienyldichlorosilane (or siloxane) with dihydroxyorganosiloxanes, six- and eight-membered organocyclosiloxanes, with one or two methylthienylsiloxy rings in the cycle, have been synthesized.”
8. Claim(s) 1-10, 20 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by
CN 103374083 A (cited on the IDS with EPO machine translation). Khananashvili discloses anticipatory compounds including but not limited to the elected species at page 15 of the translation at [0082] phenyl thiophenedimethoxysilane, of Formula I-A claim 2, where R6, R7, and R8 are H, m is 1, X is S, q is 0, R1 is methoxy, n is 2, k is 1, R4 is phenyl. The compound was made into a curable composition with propylene at paragraph [0085] and [0091] page 15-16. Other compounds are also disclosed which anticipate including n-propyl thiophenedimethoxysilane (page 10 [0048]), n-butyl thiophenedimethoxysilane (page 14 [0071]), which also read on the claims as above except where R4 is alkyl (n-propyl, n-buytl).
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 claims at issue 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); and 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 a nonstatutory double patenting ground provided the reference application or patent either is shown to be commonly owned with this application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The USPTO internet Web site contains terminal disclaimer forms which may be used. Please visit http://www.uspto.gov/forms/. The filing date of the application will determine what form 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 http://www.uspto.gov/patents/process/file/efs/guidance/eTD-info-I.jsp.
9. Claims 1-10, 20 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1- 15 of copending Application No. 18/798,973 in view of Barry Arkles “Silane Coupling Agents Connecting Across Boundaries” 2014, Gelest Inc pages 1-72. Although the claims at issue are not identical, they are not patentably distinct from each other because the curable composition claim while broader embraces the unit (B) of the instant claim 9, moreover the compositions of the ‘973 application require the compounds of the instant claims and could not be made without them. Claims 7-15 are drawn to the same substructure of claim 1. In addition using silanes to modify polymers is known in the art as disclosed in Arkles. Arkles explains that “Coupling agents find their largest application in the area of polymers.” [page 7], applications of silane modified polymers are disclosed on pages 7-10. It would be obvious to mix the silanes claimed with polymers in a composition as suggested by Arkles.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Rejections Under the Judicially Created Doctrine of Improper Markush Grouping
10. Claims 1-10 and 20 are rejected on the judicially-created basis that it contains an improper Markush grouping of alternatives. See In re Harnisch, 631 F.2d 716, 721-22 (CCPA 1980) and Ex parte Hozumi, 3 USPQ2d 1059, 1060 (Bd. Pat. App. & Int. 1984). The improper Markush grouping includes species of the claimed invention that do not share both a substantial structural feature and a common use that flows from the substantial structural feature. The members of the improper Markush grouping do not share a substantial feature and/or a common use that flows from the substantial structural feature for the following reasons: The only non-variable atoms in Formula I are a carbon and silicon atom. This structure is insubstantial to the disclosure of the compounds in the specification. According to the specification the compounds are silanes used to modify polymers.
The specification discloses only 4 compounds. These compounds are homogenous. The compounds all have a thiophene ring, at least two methoxy groups, and three simple hydrocarbon groups attached to the silicon atom (phenyl, vinyl and methyl). The claims are drawn to non-cyclic compounds and compounds where X is any heteroatom, not just S. The rings embraced by the X structure in claim 2 Formula I-A would include not just S but also N, P, Fe, As, and a large number of diverse elements. The arsoles claimed where X is As, have not been prepared. “The field of functional materials also suffered from the decline of organoarsenic chemistry. Heteroles, five-membered heterocyclopentadiene, have increasingly attracted attention in such fields. However, investigations of “arsoles” from the view-point of materials science remain to be performed, although some arsole derivatives were synthesized up to the 1960s.[4–8] If studies on pnictogen-type heteroles are performed by experimental means, pyrrole,[9–13] phosphole,[14–17] stibole,[18, 19] and bismole[20–22] derivatives are prepared, but their arsenic analogues tend to be excluded.” Imoto “The Dawn of Functional Organoarsenic Chemistry” Chem. Eur. J. 2019, 25, 1883 – 1894. “There is potential interest in arsole derivatives, as shown above, but the absence of practical synthetic methods has restricted further progress.” Assuming some could be prepared there is no expectation that such diverse compounds would have the same or similar properties. It is well known that molecular structure is correlated with physical properties and in particular in heterocyclic chemistry the change from one ring to another often results in dramatic changes in properties. Pozharskii et. al. Heterocycles in Life and Society Wiley, 1997, pgs. 1-6: "It is rumored that the Russian scientist Beketov once compared heterocyclic molecules to jewelry rings studded with precious stones. Several carbon atoms thus make up the setting of the molecular ring, while the role of the jewel is played by an atom of another element, a heteroatom. In general, it is the heteroatom which imparts to a heterocycle its distinctive and sometimes striking properties..." Remarkably the claims are broader since they also include X in any non-ring, as well and thousands of other entirely unsupported prophetic recitations. All of the compounds, have a very specific structure absent from the instant claims. In response to this rejection, Applicant should either amend the claim(s) to recite only individual species or grouping of species that share a substantial structural feature as well as a common use that flows from the substantial structural feature, or present a sufficient showing that the species recited in the alternative of the claims(s) in fact share a substantial structural feature as well as a common use that flows from the substantial structural feature. This is a rejection on the merits and may be appealed to the Board of Patent Appeals and Interferences in accordance with 35 U.S.C. §134 and 37 CFR 41.31(a)(1) (emphasis provided).
Conclusion
11. Any inquiry concerning this communication or earlier communications from the examiner should be directed to DAVID K O'DELL whose telephone number is (571)272-9071. The examiner can normally be reached on Monday - Friday 9:30 - 7:00 PM.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Clinton Brooks can be reached on 571-270-7682. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/DAVID K O'DELL/Primary Examiner, Art Unit 1621