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
Claims 1-19 of H.J. Ahn, et al., US 18/013,528 (12/28/2022) are pending. Claims 1-5 and 16-19 are withdrawn as directed to non-elected Groups. Claims 6-15 are under examination on merits and are rejected.
Election/Restrictions
Pursuant to the restriction requirement, Applicant elected Group II (claims 6-15), without traverse, in the reply filed on 12/17/2025. Claims 1-5 and 16-19 drawn to non-elected Groups I and III are withdrawn from consideration pursuant to 37 CFR 1.142(b). The Restriction requirement is made as FINAL.
Specification Objections
The specification is objected to because the chemical structures at page 4, 8, 18 and 22 are not clear enough to be recognized, which can been seen from the Pre-Grant Pub (US20230261187A1) with several “?” marks.
Claim Objections
Claims 7-12 and 14-15 are objected to on the grounds of several of improper parentheticals, for example “(In Chemical Formula 2, . . . .)” in claim 7 and “polymethylhydrosiloxane (PMHS)” in claim 10. While Applicant may intend that the parenthetical phrase adds clarification/emphasis, it is at best superfluous and better practice is to amend so as to remove the parentheticals to avoid confusion as to whether Applicant improperly intends preferences within the claim. See MPEP § 2173.05(d). Correction of all such parenthetical throughout the claims is required.
Claims 8 and 12 are further objected to because the “the remaining Rs each independently represent. . .” is required to corrected as “the remaining R’s each independently represent. . . .” to clarify the structure of the Chemical Formula 3 in claim 8 and the claimed species in claim 12.
Claim Interpretation
Examination requires claim terms first be construed in terms in the broadest reasonable manner during prosecution as is reasonably allowed in an effort to establish a clear record of what applicant intends to claim. See, MPEP § 2111. Under a broadest reasonable interpretation, words of the claim must be given their plain meaning, unless such meaning is inconsistent with the specification. See MPEP § 2111.01. It is also appropriate to look to how the claim term is used in the prior art, which includes prior art patents, published applications, trade publications, and dictionaries. MPEP § 2111.01 (III).
Interpretation of Claim Term “Plurality of Polyhedral Oligomeric Silsesquioxane”
The instant claims recite term of “plurality of polyhedral oligomeric silsesquioxane”. The specification does not provide definition for the claimed “plurality of polyhedral oligomeric silsesquioxane”. The specification has an open-end discussion for the claimed “plurality of polyhedral oligomeric silsesquioxane”as follows:
The POSS moiety 20 may be any one or a combination of the following
compounds (1) to (6). Specifically, the compound (1) has a partial cage structure, the compound (2) has a ladder structure, and the compound (3) has a random structure. The compound (4) is a case in which n in (R-SiO1.5)n is 8, the compound (5) is a case in which n in (R-SiO1.5)n is 10, and the compound (6) has a molecular structure including one cage when n in (R-SiO1.5)n is 12.
Specification at page 17, line 3-8, emphasis added.
Prior art teaches that:
[0003] Known structures for these silsesquioxanes include random structures with no specific structure, as well as double-decker structures, ladder structures and cage structures for which the structure can be determined.
See T. Tanaka, et al. US 20210061828A1 (2021)(“Tanaka”) at page 1, [0003].
Consistent with the specification and teaching from prior art, “plurality of polyhedral oligomeric silsesquioxane” is broadly and reasonably interpreted as any organosilicon compound featuring an inorganic silica-like core (Si-O-Si bonds) with at least group one organic exterior group, forming cage, ladder, double-decker, or random polymeric structures.
Interpretation of the claimed invention
The independent claim 6 does not provide definition for the claimed reaction starting materials(linear polysiloxane polymer, POSS, aromatic compound) or the prepared product.
The specification teaches that:
As shown in the following Reaction Scheme 1, in crosslinking (hydrosilylation) between a polysiloxane polymer having a Si-H group and an organic substance (aromatic compound) having a vinyl group in the presence of a platinum catalyst, a POSS is added, and thus Si-H in a terminal of the POSS participates in the hydrosilylation of the polysiloxane polymer and the aromatic compound. As a result, as shown in FIG. 1, an aerogel-type intermediate with a structure in which an organosilicon bond is formed between the linear polysiloxane polymer and the aromatic compound and between the POSS and the aromatic compound is formed.
PNG
media_image1.png
108
643
media_image1.png
Greyscale
Specification at page 24, line 10-20, emphasis added.
The specification teaches that:
The organosilicon bond between the linear polysiloxane polymer and the aromatic compound and between the POSS and the aromatic compound may be represented by the following Chemical Formula 1.
PNG
media_image2.png
275
727
media_image2.png
Greyscale
Specification at page 20, line 19 to page 21, line 5.
The specification teaches working examples as follows:
<Preparation Example 1>
8 g of acetone, 0.8 g of polymethylhydrosiloxane (PMHS), 0.2 g of pss-octakis(dimethylsilyloxy)silsesquioxane as a POSS, and 1.6 g of divinylbenzene (DVB) were continuously mixed, a platinum catalyst was added to the mixing solution, and then stirring was sufficiently performed.
The mixing solution was input into an autoclave and heated at 120 °C for 6 hours to synthesize an intermediate in the form of an aerogel.
. . .
<Preparation Example 2>
An intermediate for preparing porous SiOC was prepared in the same manner as in Preparation Example 1, except that 0.1 g of pss- octakis(dimethylsilyloxy)silsesquioxane was used.
<Preparation Example 3>
An intermediate for preparing porous SiOC was prepared in the same manner as in Preparation Example 1, except that 0.3 g of pss- octakis(dimethylsilyloxy)silsesquioxane was used.
Specification at page 34-35, Preparation Examples 1-3, emphasis added.
Consistent with the specification, the instant claim 6 is broadly and reasonably interpreted as a method of synthesis of a hybrid comprising at least one linear polysiloxane polymer and at least one a POSS, wherein the at least one linear polysiloxane polymer and the at least one a POSS are linked by an aromatic compound having two or more terminal functional groups including a vinyl group or an acetylene as schematically indicated below.
PNG
media_image3.png
937
2226
media_image3.png
Greyscale
The claim preamble “ for preparing porous silicon oxycarbide” does not result in a structural difference of the recited active steps, therefore, it is interpreted as an intended use and does not apply prior art rejections.
Claim Rejections - 35 USC § 112(b)
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.
Pursuant to 35 U.S.C. 112(b), the claim must apprise one of ordinary skill in the art of its scope so as to provide clear warning to others as to what constitutes infringement. MPEP 2173.02(II); Solomon v. Kimberly-Clark Corp., 216 F.3d 1372, 1379, 55 USPQ2d 1279, 1283 (Fed. Cir. 2000). The meaning of every term used in a claim should be apparent from the prior art or from the specification and drawings at the time the application is filed. Claim language may not be ambiguous, vague, incoherent, opaque, or otherwise unclear in describing and defining the claimed invention. MPEP § 2173.05(a).
Claim 12 is rejected under 35 U.S.C. 112(b) as indefinite because the limited structures are not clear, for example, one ordinary skill does not know which atom is bonded by the oxygen atom in the claimed species 1’ as indicated below.
PNG
media_image4.png
339
368
media_image4.png
Greyscale
Applicant is required to provided clear chemical structure for each and every claimed compound.
Claims 8 and 12 are rejected under 35 U.S.C. 112(b) as indefinite because structure of the claimed R’ is not clear. Claim 8 defines the claimed R’ as:
. . .at least two of the 8 to 16 R's represent -OSi2HRARB involved in the hydrosilylation, . . . .
the remaining R’s each independently represent any one of a hydrogen atom, a halogen atom, a hydroxy, a C1 to C20 linear or branched alkyl, alkene, alkyne, or alkoxy, a C5 to C20 aryl, and -OSir1r2r3, . . .
It is not clear what is the structure of the moiety of -OSi2HRARB.
It also is not clearly whether -OSir1r2r3 is one alternative group, or the remaining R’s must comprise the group of-OSir1r2r3. Applicant is reminded to use the following standard language in defining a Markush grouping:
“wherein the alternative is selected from the group consisting of A, B, C and D”; or
“wherein the alternative is A, B, C or D”. See MPEP § 2173.05(h).
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.
35 USC § 103 Rejection over Shi and Sasikumar
Claims 6-7, 9-11 and 13-15 are rejected under 35 U.S.C. 103 as being unpatentable over Y. Shi, et al. 20.9 Journal of Polymer Research 245 (2013)(“Shi”) in view of P. Vallachira Warriam Sasikumar, Pradeep, et al. 99.9 Journal of the American Ceramic Society 2977-2983 (2016)(“Sasikumar”).
Y. Shi, et al. 20.9 Journal of Polymer Research 245 (2013)(“Shi”)
Shi teaches a method of preparing vulcanized (RTV) silicone rubber containing POSS units in polysiloxane main chains as indicated below..
PNG
media_image5.png
822
723
media_image5.png
Greyscale
Shi at page 3 of 11, Scheme 1
Shi teaches that two steps is conducted to prepare DOPO-PDMS form DHPO:
(i). hydrosilylating of DHPO (0.00413 mol) with
PNG
media_image6.png
140
418
media_image6.png
Greyscale
in the presence of Pt(dvs) to form an intermediate DOPO.
(ii). hydrosilylating of polymethylhydrosiloxane with DOPO in the presence of dibutyltin dilaurate to form the hybrid of DOPO-PDMS.
See Shi at page 2 of 11, Experimental, right col, Synthesis of ethyoxyl-phenyl POSS (DOPO) [Ph8Si10O14(OCH3)2Me2] and Synthesis of poly(dimethylsiloxane)s with POSS
in the polysiloxane main chain (DOPO-PDMS).
Thus, Shi teaches a method of preparation of the compound DOPO-PDMS through hydrosilylating of DHPO that is a POSS and polymethylhydrosiloxane that is a linear polysiloxane polymer with the compound of
PNG
media_image6.png
140
418
media_image6.png
Greyscale
; wherein,
PNG
media_image6.png
140
418
media_image6.png
Greyscale
forms an organosilicon bond with polymethylhydrosiloxane and DHPO respectively.
Difference between Shi and the Claims
The Shi method differs from the instant claim 6 only in that the compound of
PNG
media_image6.png
140
418
media_image6.png
Greyscale
is not an aromatic compound having two or more terminal functional groups including a vinyl group or an acetylene.
P. Vallachira Warriam Sasikumar, Pradeep, et al. 99.9 Journal of the American Ceramic Society 2977-2983 (2016)(“Sasikumar”)
Sasikumar teaches a method of cross-linking a linear polyhydridomethylsiloxane (PHMS) with divinylbenzene through a hydrosilyation reaction between the Si-H moieties of the PHMS and the CH2=CH- group of the divinylbenzene. Sasikumar at page 2978, left col. (1) Material Synthesis, emphasis added.
Obviousness Rational of the Claims 6-11 and 13-15
Claims 6 and 15 are obvious because one ordinary skill seeking enhance the stability of vulcanized (RTV) silicone rubber is motivated to modify the Shi method by replacing
PNG
media_image6.png
140
418
media_image6.png
Greyscale
with divinylbenzene as indicated below, thus arrive at a method meeting each and every limitation of claims 6 and 15, therefore, claims 6 and 15 are obvious.
PNG
media_image7.png
1495
2918
media_image7.png
Greyscale
One ordinary skill has a motivation to do so with a reasonable expectation of success because:
(i). Shi teaches that incorporation a POSS into a vulcanized (RTV) silicone rubber via chemical bonds can improve thermal stability mechanical properties of vulcanized (RTV) silicone rubber. See Shi at page 1 of 11, right col. line 1-12 and page 10 of11, right col. Conclusion, line 1;
(ii) Sasikumar teaches that divinylbenzene can be used as a cross-linking agent for polysiloxanes through a hydrosilyation reaction between the Si-H moieties of the PHMS and the CH2=CH- group of the divinylbenzene;
(iii) replacing of replacing
PNG
media_image6.png
140
418
media_image6.png
Greyscale
with divinylbenzene can conduct the two step reactions in one-pot manner because both of the proposed steps are reaction between Si-H moieties with CH2=CH- group of the divinylbenzene with the same catalyst.
Claims 7 and 10 are obvious because Shi teaches that the polymethylhydrosiloxane has a formula of
PNG
media_image8.png
172
267
media_image8.png
Greyscale
that maps the Chemical Formula 2 as both R1 and R2 are methyl groups.
Claims 9 and 14 are obvious because as indicated above that the proposed compound has organosilicon bonds formed between divinylbenzene with polymethylhydrosiloxane and DHPO respectively has a formula of:
PNG
media_image9.png
676
1348
media_image9.png
Greyscale
Which maps the Chemical Formula 1 in claim 9 and the Chemical Formula 4 in claim 14 as:
Ar is a C6 arylene
Each of Ra, Rb and Rc is hydrogen atom;
Each of Y1 and Y2 is a bond; and
Each of n and m is 1.
Claim 11 is obvious because one ordinary skill is motivated to conduct the propose method with polymethylhydrosiloxane having different polymerization degree so that can optimize the property of vulcanized (RTV) silicone rubber; the weight average molecular weight of
PNG
media_image8.png
172
267
media_image8.png
Greyscale
is between 400 and 10000 when its polymerization degree is 10.
Claim 13 is obvious because as indicated above that the DHPO has a cage structure.
35 USC § 103 Rejection over Shi, Sasikumar and Januszewski
Claims 8 and 12 are rejected under 35 U.S.C. 103 as being unpatentable over Y. Shi, et al. 20.9 Journal of Polymer Research 245 (2013)(“Shi”) in view of P. Vallachira Warriam Sasikumar, Pradeep, et al. 99.9 Journal of the American Ceramic Society 2977-2983 (2016)(“Sasikumar”) as applied above for the rejection of claim 6 further in view of D. Chen, et al. 51.17 Polymer 3867-3878 (2010)(“Chen”) and M. Grzelak, et al. 49.16 Dalton Transactions 5055-5063 (03/16/2020)(“Grzelak”).
The Combination of Shi and Sasikumar
As detail discussed above that the combination of Shi and Sasikumar teaches a method meeting each and every limitation of the instant claim 6.
Difference between the Combination and Claims 8 and 12
The method taught by the combination differs claim 8 in that the Shi DPHO does not meet the structural limitation of the Chemical Formula 3; the combination differs claim 12 in that the Shi DPHO is not one of the claimed species.
D. Chen, et al. 51.17 Polymer 3867-3878 (2010)(“Chen”)
Similar as Shi, Chen also studied on vulcanized (RTV) silicone rubber containing POSS units in polysiloxane main chains as indicated below.
PNG
media_image10.png
911
869
media_image10.png
Greyscale
Chen at page 3871, Scheme 1.
Chen teaches that:
Morphologies, thermal properties, mechanical properties and hardness of these novel RTV silicone rubbers were studied. The results exhibited significantly enhanced effects of POSS on thermal stabilities, mechanical properties and hardness as compared to the PDMS polymers prepared with the traditional tetra-functional TMOS and TEOS cross-linkers. The striking improvements in thermal properties, mechanical properties and hardness could be attributed to the synergistic effect of the increase of dimensionality of cross-linked networks in novel RTV silicone rubbers resulting from special three-dimensional structure of novel POSS cross-linkers, plasticization of self-cross-linked POSS cross-linkers and uniform distribution of POSS cross-linkers.
Chen at abstract line 6-14, emphasis added.
Thus, Chen teaches one ordinary skill that increasing of dimensionality of cross-linked networks can enhance of thermal properties, mechanical properties and hardness of vulcanized (RTV) silicone rubber.
M. Grzelak, et al. 49.16 Dalton Transactions 5055-5063 (03/16/2020)(“Grzelak”)
Grzelak teaches a octafunctionalized POSS 7 that can be hydrosilylation with -CH=CH2 with more than 99% SiH conversion and more than 91% yield as indicated below. Grzelak at page 5060, left col. Scheme 6 and Table 3.
PNG
media_image11.png
674
670
media_image11.png
Greyscale
The Grzelak compound 7 maps the Chemical Formula 3 in claim 8 as R’ is -OSiH(CH3)2 and n is 8; it is the claimed species 4’ in claim 12 wherein each of the R’ is -OSiH(CH3)2.
Obviousness Rational of the Claims 8 and 12
Claims 8 and 12 are obvious because one ordinary skill is motivated to modify the above proposed method by replacing the Shi DPHO with Grzelak compound 7 as indicated below, thus arrive at a method meeting each and every limitation of claims 8 and 12, therefore, claims 8 and 12 are obvious.
PNG
media_image12.png
1983
2466
media_image12.png
Greyscale
One ordinary skill is motivated to do so with a reasonable expectation of success because by replacing the Shi DPHO with Grzelak compound 7 will increase the cross-linking density of the proposed vulcanized RTV silicone rubber as Chen teaches that increasing of dimensionality of cross-linked networks can enhance of thermal properties, mechanical properties and hardness of vulcanized (RTV) silicone rubber.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to FRANK S. HOU whose telephone number is (571)272-1802. The examiner can normally be reached 6:30 am-2:30 pm Eastern on Monday to Friday.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at (571)2705241.
The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/FRANK S. HOU/Examiner, Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692