Prosecution Insights
Last updated: October 02, 2026
Application No. 18/556,407

METHODS OF ATTACHING AZIDE COMPOUNDS TO SURFACES AND COMPOUNDS AND PRODUCTS THEREOF

Non-Final OA §102§103§112
Filed
Oct 20, 2023
Priority
May 20, 2021 — provisional 63/191,032 +1 more
Examiner
PEPITONE, MICHAEL F
Art Unit
1767
Tech Center
1700 — Chemical & Materials Engineering
Assignee
Vanderbilt University
OA Round
1 (Non-Final)
74%
Grant Probability
Favorable
1-2
OA Rounds
1m
Est. Remaining
96%
With Interview

Examiner Intelligence

Grants 74% — above average
74%
Career Allowance Rate
894 granted / 1201 resolved
+9.4% vs TC avg
Strong +22% interview lift
Without
With
+21.9%
Interview Lift
resolved cases with interview
Typical timeline
3y 0m
Avg Prosecution
39 currently pending
Career history
1236
Total Applications
across all art units

Statute-Specific Performance

§101
2.0%
-38.0% vs TC avg
§103
41.7%
+1.7% vs TC avg
§102
22.2%
-17.8% vs TC avg
§112
20.7%
-19.3% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1201 resolved cases

Office Action

§102 §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 . Claim Objections Claim 13 is objected to because of the following informalities: “azid.” Should be “azide.”. Appropriate correction is required. 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. Claims 7, 10, 31-32, and 40-42 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. A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claim 7 recites the broad recitation RUR is an unsaturated reactive group, and the claim also recites RUR is an alkenyl group, an alkynyl group, a carbonyl group, a ketone group, an aldehyde group, a nitrile group, or an amine group which is the narrower statement of the range/limitation. In the present instance, claim 10 recites the broad recitation halide or leaving group, and the claim also recites alkyl halide, a benzyl halide, an aryl halide, or a sulfonate ester which is the narrower statement of the range/limitation. In the present instance, claim 31 recites the broad recitation unsaturated reactive group (RUR), and the claim also recites RUR is an alkenyl group, an alkynyl group, a carbonyl group, a ketone group, an aldehyde group, a nitrile group, or an amine group which is the narrower statement of the range/limitation. In the present instance, claim 32 recites the broad recitation unsaturated reactive group (RUR), and the claim also recites RUR is an alkenyl group, an alkynyl group, a carbonyl group, a ketone group, an aldehyde group, a nitrile group, or an amine group which is the narrower statement of the range/limitation. In the present instance, claim 40 recites the broad recitation RUR is an unsaturated reactive group, and the claim also recites RUR is an alkenyl group, an alkynyl group, a carbonyl group, a ketone group, an aldehyde group, a nitrile group, or an amine group which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims. Accordingly, dependent claims 41-42 are indefinite. Claim Rejections - 35 USC § 102 In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status. 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. Claim(s) 1-3, 5, 7-10, 32 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Storti et al. (EP 3 495 040). Regarding claims 1-3, 5, 7-9, and 32: Storti et al. (EP ‘040) discloses a method of preparing surface-functionalized micro-clusters [abstract], wherein 4-vinylbenzyl azide (VBA) is crosslinked onto a styrene (St) / divinyl benzene (DVB) core to afford a shell containing azide functionality [0011-0013]. Storti et al. (EP ‘040) discloses the St/DVB core particles were produced via emulsion polymerization [0043-0044] and the VBA shell was polymerized onto the St/DVB core particles in the presence of KPS (potassium persulfate [0079]) initiator [0044-0045]. Note VBA: PNG media_image1.png 200 400 media_image1.png Greyscale [0011; 0042]. Regarding claim 10: Storti et al. (EP ‘040) discloses 4-vinylbenzyl azide (VBA) was prepared by reacting sodium azide with 4-vinylbenzyl chloride: PNG media_image2.png 232 330 media_image2.png Greyscale [0011; 0042]. Claim(s) 1-6 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Goldman, A. S.; Walther, A.; Nebhani, L.; Joso, R.; Ernst, D.; Loos, K.; Barner-Kowollik, C.; Barner, L.; Müller, A. H. E. Macromolecules, 2009, 42, 3707-3714 [IDS 10/20/23]. Regarding claims 1-6: Goldman et al. (Macromolecules, 2009, 42, 3707-3714) discloses a method of surface modifying microspheres [abstract; Scheme 2], wherein poly(divinylbenzene) microspheres (pDVB80) were reacted with 1-azido-undecan-11-thiol and AIBN (2,2’-azobisisobutyronitrile) in acetonitrile as solvent for 72 h under reflux. The resulting azide functionalized microspheres (pDVB-N3) were isolated by filtration, washed with tetrahydrofuran, ethanol and acetone, followed by Soxhlet extraction in acetonitrile to remove any unreacted compounds [§ Experimental Section]. Note pDVB-N3: PNG media_image3.png 134 354 media_image3.png Greyscale [pDVB-N3; Scheme 2]. Claim(s) 1-3, 7, 10, 13, and 32 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Delapierre et al. (US 2009/0188602). Regarding claims 1-3, 7, 13, and 32: Delapierre et al. (US ‘602) discloses a method of grafting molecules on a silicon substrate [abstract], wherein the prepared silicon surface of Ex. 4 [Ex. 4; 0106-0119] was immersed in a solution of undecenyl azide (spacer compound of Formula (I) [Ex. 1; 0084-0085]) in mesitylene and reacted for 12 h at 150 oC to afford a silicon substrate having azide functionality [Ex. 4; 010-0119; Scheme A]. Note undecenyl azide: PNG media_image4.png 66 386 media_image4.png Greyscale [Ex. 1; 0084-0085]; Scheme A: PNG media_image5.png 478 456 media_image5.png Greyscale [Ex. 4; 0109-0112; Scheme A]. Regarding claim 10: Delapierre et al. (US ‘602) discloses undecenyl azide was prepared by reacting undecenyl bromide with sodium azide [Ex. 1; 0084-0085]. Claim(s) 34-35 and 38-40 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Delapierre et al. (US 2009/0188602). Regarding claims 34-35 and 38-40: Delapierre et al. (US ‘602) discloses grafted molecules on a silicon substrate [abstract], wherein the prepared silicon surface of Ex. 4 [Ex. 4; 0106-0119] was immersed in a solution of undecenyl azide (spacer compound of Formula (I) [Ex. 1; 0084-0085]) in mesitylene and reacted for 12 h at 150 oC to afford a silicon substrate having azide functionality [Ex. 4; 010-0119; Scheme A]. Note undecenyl azide: PNG media_image4.png 66 386 media_image4.png Greyscale [Ex. 1; 0084-0085]; Scheme A: PNG media_image5.png 478 456 media_image5.png Greyscale [Ex. 4; 0109-0112; Scheme A]. 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. 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) 8-9 and 31 is/are rejected under 35 U.S.C. 103 as being unpatentable over Delapierre et al. (US 2009/0188602) as applied to claim 1 above. Regarding claims 8-9: Delapierre et al. (US ‘602) discloses the basic claimed method [as set forth above with respect to claim 1]; wherein Delapierre et al. (US ‘602) discloses the spacer compound of Formula (I) having X as C=C, Y as azide, and E as aryl radicals [0024-0035]. Delapierre et al. (US ‘602) does not specifically disclose the organic azide of instant claims 8-9. However, a prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979) [See MPEP 2144.09]. Regarding claim 31: Delapierre et al. (US ‘602) discloses the basic claimed method [as set forth above with respect to claim 1]; wherein Delapierre et al. (US ‘602) discloses the spacer compound of Formula (I) having X as C=C, Y as azide, and E as alkyl radicals having 1-20 carbon atoms [0024-0035]. Delapierre et al. (US ‘602) does not specifically disclose a polymer. However, a prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979) [See MPEP 2144.09]. Compounds which homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977) [See MPEP 2144.09]. Claim(s) 41-42 is/are rejected under 35 U.S.C. 103 as being unpatentable over Delapierre et al. (US 2009/0188602) as applied to claim 40 above. Regarding claims 41-42: Delapierre et al. (US ‘602) discloses the basic claimed material [as set forth above with respect to claim 40]; wherein Delapierre et al. (US ‘602) discloses the spacer compound of Formula (I) having X as C=C, Y as azide, and E as aryl radicals [0024-0035]. Delapierre et al. (US ‘602) does not specifically disclose the organic azide of instant claims 41-42. However, a prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979) [See MPEP 2144.09]. See attached form PTO-892. Correspondence Any inquiry concerning this communication or earlier communications from the examiner should be directed to MICHAEL F PEPITONE whose telephone number is (571)270-3299. The examiner can normally be reached on 7:00 AM - 3:30 PM. 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, Mark Eashoo can be reached on 571-272-1197. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of an application may be obtained from the Patent Application Information Retrieval (PAIR) system. Status information for published applications may be obtained from either Private PAIR or Public PAIR. Status information for unpublished applications is available through Private PAIR only. For more information about the PAIR system, see http://pair-direct.uspto.gov. Should you have questions on access to the Private PAIR system, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative or access to the automated information system, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /MICHAEL F PEPITONE/Primary Examiner, Art Unit 1767
Read full office action

Prosecution Timeline

Oct 20, 2023
Application Filed
Aug 26, 2026
Non-Final Rejection mailed — §102, §103, §112 (current)

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Study what changed to get past this examiner. Based on 5 most recent grants.

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Prosecution Projections

1-2
Expected OA Rounds
74%
Grant Probability
96%
With Interview (+21.9%)
3y 0m (~1m remaining)
Median Time to Grant
Low
PTA Risk
Based on 1201 resolved cases by this examiner. Grant probability derived from career allowance rate.

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