Prosecution Insights
Last updated: July 17, 2026
Application No. 18/877,677

CYANATE ESTERS AS MONOMERS IN POLYMERIZABLE COMPOSITIONS

Non-Final OA §103§112
Filed
Dec 20, 2024
Priority
Jun 23, 2022 — AT A 60091/2022 +3 more
Examiner
YE, XINWEN
Art Unit
1754
Tech Center
1700 — Chemical & Materials Engineering
Assignee
Technische Universität Wien
OA Round
1 (Non-Final)
44%
Grant Probability
Moderate
1-2
OA Rounds
1y 6m
Est. Remaining
89%
With Interview

Examiner Intelligence

Grants 44% of resolved cases
44%
Career Allowance Rate
51 granted / 117 resolved
-21.4% vs TC avg
Strong +45% interview lift
Without
With
+45.2%
Interview Lift
resolved cases with interview
Typical timeline
3y 1m
Avg Prosecution
36 currently pending
Career history
169
Total Applications
across all art units

Statute-Specific Performance

§101
0.8%
-39.2% vs TC avg
§103
90.2%
+50.2% vs TC avg
§102
2.6%
-37.4% vs TC avg
§112
2.6%
-37.4% vs TC avg
Black line = Tech Center average estimate • Based on career data from 117 resolved cases

Office Action

§103 §112
DETAILED ACTION 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 . Priority Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55. Information Disclosure Statement The information disclosure statement (IDS) submitted on 06/17/2025 was filed in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner. 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 27 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. Claim 27 recites the limitation “for several hours and/or…for several days”. The metes and bounds of the term “several” are unclear which renders the claim indefinite. 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. This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention. Claim(s) 11-22 and 26-27 are rejected under 35 U.S.C. 103 as being unpatentable over US2019/0010343 (“Menyo et al” hereinafter Menyo) and US2022/0213245 (“Snow et al” hereinafter Snow) and US2021/0162657 (“Chartrain et al” hereinafter Chartrain). Regarding Claim 11, Menyo teaches a method of 3D printing a solid article from a polymerizable composition ([0002] and [0008]-[0023]) comprising cyanate ester monomers ([0043]), at least one polymerization initiator ([0038]), and a co-catalyst ([0042]), wherein: (a) the cyanate ester monomers comprise multifunctional cyanate esters having formula R(OCN)n, wherein R is an n-valent carbohydrate residue having up to 50 carbon atoms and n is an integer > 2 ([0043]-[0044] and Formula I); and (c) the co-catalyst comprises a compound comprising at least one acidic hydrogen atom ([0054]); the 3D printing method ([0008]-[0012])comprising: (i) a homogeneous liquid mixture ([0133], the mixture is mixed in a centrifugal mixer to yield homogeneous resin) (ii) irradiating the homogeneous mixture ([0133], the mixture is mixed in a centrifugal mixer to yield homogeneous resin) at at least the heating temperature with a wavelength suitable to activate the photoinitiator and to obtain a three-dimensional solid article ([0133], resin was formed into a three dimensional intermediate using CLIP using LED projector and cured at desired temperature to yield the desired product). Menyo fails to explicitly teaches the polymerization initiator is an organometallic polymerization initiator and (b) the organometallic polymerization initiator is an organometallic photoinitiator. However, Snow teaches the polymerization initiator is an organometallic polymerization initiator ([0007]) and (b) the organometallic polymerization initiator is an organometallic photoinitiator ([0014], a combination of at least one metallocene compound comprising, consisting essentially of or consisting of a transition metal of Group VIII of the periodic table and aromatic electron system ligands and at least one photocleavable compound which generates an acyl radical when exposed to light. [0016], the metallocene compound comprises a transition metal selected from the group consisting of iron, osmium, and ruthenium. Iron - containing metallocenes , i.e. , ferrocenes , are employed in certain aspects of the invention. Ferrocenes are a known organometallic photoinitiator). Menyo and Snow are considered to be analogous to the claimed invention because both are in the same field of preparing photocurable compositions to be used in the field of stereolithography to generated a 3D object. Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modified the polymerization initiator discloses by Menyo such that it teaches all of the above mentioned limitations as taught by Snow because utilizing one known photoinitiator material in place of another photoinitiator material also suitability in the field of stereolithography is well within the ambit of one of ordinary skill in the art. See MPEP 2144.07. The modified Menyo fails to teach initially heating the composition to a heating temperature of > 70°C to obtain liquid mixture. However, Chartrain teaches initially heating the composition to a heating temperature of > 70°C to obtain a liquid mixture ([0031], the resin is heated uniformly in the vat to an elevated temperature is about 50° C., 80° C., 100° C., or 120° C.). Menyo and Chartrain are considered to be analogous to the claimed invention because both are in the same field of preparing photocurable compositions to be used in the field of stereolithography to generated a 3D object. Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the method disclosed by the modified Menyo such that it teaches the above mentioned limitations as taught by Chartrain to avoids distortions in the optical and mechanical properties of the resin ([0031]). Since the claimed range overlaps or lies inside ranges disclosed by the prior art, a prima facie case of obviousness exists. Please see MPEP 2144.05(I) and In re Wertheim, 541 F.2d 257, 191USPQ 90 (CCPA 1976) for further details. Regarding Claim 12, the modified Menyo teaches the method according to claim 11, wherein the cyanate ester monomers comprise multifunctional aromatic cyanate esters (Menyo, [0019]-[0020]). Regarding Claim 13, the modified Menyo teaches the method according to claim 11, wherein the cyanate ester monomers comprise cyanates of bisphenol (Menyo, [0050], the cyanate ester compound is selected as cyanated bisphenol polycarbonate oligomers produced by reacting a bisphenol polycarbonate oligomer with cyanogen halide) or novolak derivatives. Regarding Claim 14, the modified Menyo teaches the method according to claim 11, wherein in the formula R(OCN)n (Menyo, Formula I and [0019]), R comprises up to 40 carbon atoms ([0019]-[0020]); and/or n=2 to 4 ([0019]-[0020]). Regarding Claim 15, the modified Menyo teaches the method according to claim 11, wherein the composition is initially heated to a temperature of 80°C to 100°C before step (ii) (Chartrain, ([0031], the resin is heated uniformly in the vat to an elevated temperature is about 50° C., 80° C., 100° C., or 120° C). Since the claimed range overlaps or lies inside ranges disclosed by the prior art, a prima facie case of obviousness exists. Please see MPEP 2144.05(I) and In re Wertheim, 541 F.2d 257, 191USPQ 90 (CCPA 1976) for further details. Regarding Claim 16, the modified Menyo teaches the method according to claim 15, wherein the composition is initially heated to a temperature of 80°C to 90°C before step (ii) (Chartrain, ([0031], the resin is heated uniformly in the vat to an elevated temperature is about 50° C., 80° C., 100° C., or 120° C). Since the claimed range overlaps or lies inside ranges disclosed by the prior art, a prima facie case of obviousness exists. Please see MPEP 2144.05(I) and In re Wertheim, 541 F.2d 257, 191USPQ 90 (CCPA 1976) for further details. Regarding Claim 17, the modified Menyo teaches the method according to claim 11, wherein the organometallic photoinitiator comprises an organometallic complex of an Al, Fe (Snow, [0007], photoinitiator consisting of transition metal Fe), Mn, Ru, Zn, Co or Cu ion. Regarding Claim 18, the modified Menyo teaches the method according to claim 17, wherein the organometallic photoinitiator comprises an organometallic complex of an Fe ion (Snow, [0007], photoinitiator consisting of transition metal Fe). Regarding Claim 19, the modified Menyo teaches the method according to claim 17, wherein the organometallic complex is a sandwich or semi-sandwich compound (Snow, [0014] and [0016], the photoinitiator may be ferrocenes, which is a known semi-sandwich compound). Regarding Claim 20, the modified Menyo teaches the method according to claim 19, wherein the organometallic complex is a sandwich compound (Snow, [0014] and [0016], the photoinitiator may be ferrocenes, which is a known semi-sandwich compound) or semi-sandwich carbonyl complex. Regarding Claim 21, the modified Menyo teaches the method according to claim 11, wherein the co-catalyst comprises a phenol derivative (Menyo, [0055], the nucleophilic co–catalyst selected from the group consisting of nonylphenol). Regarding Claim 22, the modified Menyo teaches the method according to claim 21, wherein the co-catalyst comprises nonylphenol (Menyo, [0055], the nucleophilic co-catalyst selected from the group consisting of nonylphenol) or bisphenol A. Regarding Claim 26, the modified Menyo teaches the method according to claim 11, further comprising thermal post-curing after step (ii) (Menyo, [0133], the formed material was washed and cured for 30 minutes at 140° C, 30 minutes at 160° C, 2 hours at 180° C, 1 hour at 220° C, and 1 hour at 240° C to yield the desired product). Regarding Claim 27, the modified Menyo teaches the method according to claim 26, wherein the thermal post-curing is conducted by heating to a temperature > 200°C for several hours (Menyo, [0133], the formed material was washed and cured for 30 minutes at 140° C, 30 minutes at 160° C, 2 hours at 180° C, 1 hour at 220° C, and 1 hour at 240° C to yield the desired product; Due to lack of specific definition for the term “several hours”, the Examiner is interpreting the limitation as more than one hour and Menyo discloses post heating at temperature above 200°C for two hours) and/or heating to a temperature < 200°C for several days. Claim 23 is rejected under 35 U.S.C. 103 as being unpatentable over US2019/0010343 (“Menyo et al” hereinafter Menyo) and US2022/0213245 (“Snow et al” hereinafter Snow) and US2021/0162657 (“Chartrain et al” hereinafter Chartrain) as applied to claim 11 above, and further in view of US2023/0139931 (“Boydston et al” hereinafter Boydston). Regarding Claim 23, the modified Menyo teaches the method according to claim 11, but fails to teach wherein the polymerizable composition further comprises an oxidizing agent. However, Boydston teaches the polymerizable composition further comprises an oxidizing agent ([0041], the curable compositions may also comprise a redox agent, i.e., either a reducing agent or an oxidizing agent, depending upon the type of oxidation change being induced in the metal). Menyo and Boydston are considered to be analogous to the claimed invention because both are in the same field of preparing photocurable compositions to be used in the field of stereolithography to generated a 3D object. Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modified the method disclosed by the modified Menyo such that it teaches the above mentioned limitations as taught by Boydston to induce oxidation reaction within the composition ([0041]). Claim(s) 24-25 are rejected under 35 U.S.C. 103 as being unpatentable over US2019/0010343 (“Menyo et al” hereinafter Menyo) in view of US2022/0213245 (“Snow et al” hereinafter Snow), US2021/0162657 (“Chartrain et al” hereinafter Chartrain) and US2023/0139931 (“Boydston et al” hereinafter Boydston) as applied to claim 23 above, and further in view of US2013/0084543 (“Liska et al” hereinafter Liska). Regarding Claim 24, the modified Menyo teaches the method according to claim 23, but fails to teach wherein the polymerizable composition further comprises an organic oxidizing agent. However, Liska teaches the polymerizable composition further comprises an organic oxidizing agent ([0074]). Menyo (abstract) and Liska ([0194]) are considered to be analogous to the claimed invention because both are in the same field of preparing photocurable compositions to be used in the field of stereolithography to generated a 3D object. Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modified the method disclosed by the modified Menyo such that it teaches the above mentioned limitations as taught by Liska to generates initiating of species that are capable of causing curing ([0072]). Regarding Claim 25, the modified Menyo teaches the method according to claim 24, wherein the organic oxidizing agent comprises di-tert-butyl peroxide (Liska, [0074]). Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to XINWEN (Cindy) YE whose telephone number is (571)272-3010. The examiner can normally be reached Monday - Thursday 8:30 - 17:00. 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, Susan Leong can be reached at (571) 270-1487. 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. XINWEN (CINDY) YE Examiner Art Unit 1754 /MATTHEW J DANIELS/Primary Examiner, Art Unit 1742
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Prosecution Timeline

Dec 20, 2024
Application Filed
Jun 09, 2026
Non-Final Rejection mailed — §103, §112 (current)

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Prosecution Projections

1-2
Expected OA Rounds
44%
Grant Probability
89%
With Interview (+45.2%)
3y 1m (~1y 6m remaining)
Median Time to Grant
Low
PTA Risk
Based on 117 resolved cases by this examiner. Grant probability derived from career allowance rate.

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