Prosecution Insights
Last updated: April 19, 2026
Application No. 18/359,148

POLYFUNCTIONALIZED MACROMOLECULAR PHOTOINITIATOR CONTAINING ALPHA-AMINOKETONE, AND PREPARATION AND APPLICATION THEREOF

Non-Final OA §103
Filed
Jul 26, 2023
Examiner
EOFF, ANCA
Art Unit
1722
Tech Center
1700 — Chemical & Materials Engineering
Assignee
Inner Mongolia Yangfan New Material Co. Ltd.
OA Round
1 (Non-Final)
80%
Grant Probability
Favorable
1-2
OA Rounds
2y 10m
To Grant
91%
With Interview

Examiner Intelligence

Grants 80% — above average
80%
Career Allow Rate
982 granted / 1230 resolved
+14.8% vs TC avg
Moderate +11% lift
Without
With
+11.3%
Interview Lift
resolved cases with interview
Typical timeline
2y 10m
Avg Prosecution
48 currently pending
Career history
1278
Total Applications
across all art units

Statute-Specific Performance

§101
0.2%
-39.8% vs TC avg
§103
47.1%
+7.1% vs TC avg
§102
20.0%
-20.0% vs TC avg
§112
20.0%
-20.0% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1230 resolved cases

Office Action

§103
DETAILED ACTION The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA. Claims 1-17 are pending. The copy foreign priority application No.202210246991.6 filed in China on March 14, 2022 has not been made of record in this application. Drawings The drawings are objected to because in fig. 5 the y-axis is not labeled and no numerical values are shown on the y-axis . Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance. 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. Claim s 1, 2, and 13-17 are rejected under 35 U.S.C. 103 as being unpatentable over Yamato et al. (EP 1 177 182 B1) in view of Temel et al. (“Synthesis of Main Chain Polymeric Benzophenone Photoinitiator via Thiol-ene Click Chemistry and Its Use in Free Radical Polymerization”). With regard to claim 1, Yamato et al. teach a photoinitiator having a vinyl group of formula: (par.0004), which is a double bond-containing a -aminoketone photoinitiator A , but fail to teach a polyfunctionalized macromolecular photoinitiator prepared from the double bond-containing a -aminoketone photoinitiator A and a polythiol compound B through thiol-ene click reaction. Temel et al. teach the synthesis of polymeric photoinitiator via thiol-ene click chemistry (abstract). Polymeric photoinitiators combine the properties of a polymer with those of low molecular weight photoinitiators. Solubility and miscibility problems often observed with coatings containing low molecular weight photoinitiators do not occur with polymeric ones since polymers are easily miscible with the resin to be cured as well as with the final cured film. Moreover, odor and toxicity problems do not occur with macrophotoinitiators owing to the low volatility of the large molecules. The low migration tendency of polymeric photoinitiators and of photoproducts means that cured coatings are less prone to yellowing (page 5306). Temel et al. further teach the reaction of bisallyl-benzophenone with a dithiol in a thiol-ene polymerization to obtain a polymeric photoinitiator: (Scheme 2 on page 5307). It would have been obvious to one of ordinary skill in the art to react with HS-CH 2 -CH 2 -SH in a thiol-ene polymerization in order to obtain a polymeric photoinitiator with good solubility and miscibility , low odor and toxicity. HS-CH 2 -CH 2 -SH is a polythiol compound B, and the polymeric photoinitiator of Yamato modified by Temel is a polyfunctionalized macromolecular photoinitiator prepared from the double bond-containing a -aminoketone photoinitiator A and a polythiol compound B through thiol-ene click reaction. With regard to claim 2, is a double-bond containing a -aminoketone photoinitiator A wherein R 1 and R 2 are C 1 alkyl groups and X is an unsubstituted alkyl group with 1 carbon atom. With regard to claims 13-16, Temel et al. teach that the polymeric initiator may be used in an amount of 1wt% in a polymerizable composition and the polymerizable compound represents 10wt% (see figure 7 on page 5310). is a derivative of , which is UV-sensible (see the attached “2-methyl-4’-(methylthio)-2-Morpholinopropiophenone”). With regard to claim 17, Temel et al. teach the use of polymeric initiator for the polymerization of HDDA (1,6-hexanediol diacrylate) (see figure 7 on page 5310), which is a monomer. Claim s 4 and 5 are rejected under 35 U.S.C. 103 as being unpatentable over Yamato et al. (EP 1 177 182 B1) in view of Temel et al. (“Synthesis of Main Chain Polymeric Benzophenone Photoinitiator via Thiol-ene Click Chemistry and Its Use in Free Radical Polymerization”) as applied to claim 1 and in further view of Yang (“Health Safety Research Progress of Photoinitiators”, made of record by the applicant on July 26, 2023). With regard to claim 4, Yamato modified by Temel teach the photoinitiator in claim 1 (see paragraph 6 above), but fail to teach that the polythiol compound B is a trithiol or tetrathiol. However, Yang teaches that a tetrathiol of formula: may be used in a thiol-ene reaction with a photo initiator comprising a double bond in order to obtain a polymeric photo initiator (see page 108). Therefore, it would have been obvious to one of ordinary skill in the art before the filing date of the claimed invention to use a tetrathiol of formula: as the polythiol in a thiol-ene reaction with of Yamato modified by Temel in order to obtain a polymeric photo initiator. The tetrathiol above meets the limitations of claim 4 . With regard to claim 5, the tetrathiol above is the compound of formula B1. Claim s 1-3 and 13-17 are rejected under 35 U.S.C. 103 as being unpatentable over Ming et al. (CN 114605572 A, with attached machine translation) in view of Temel et al. (“Synthesis of Main Chain Polymeric Benzophenone Photoinitiator via Thiol-ene Click Chemistry and Its Use in Free Radical Polymerization”). With regard to claim 1, Ming et al. teach a vinyl modified a -aminoketone photoinitiator of formula (I): (abstract ) which is a double bond-containing a -aminoketone photoinitiator A , but fail to teach a polyfunctionalized macromolecular photoinitiator prepared from the double bond-containing a -aminoketone photoinitiator A and a polythiol compound B through thiol-ene click reaction. Temel et al. teach the synthesis of polymeric photoinitiator via thiol-ene click chemistry (abstract). Polymeric photoinitiators combine the properties of a polymer with those of low molecular weight photoinitiators. Solubility and miscibility problems often observed with coatings containing low molecular weight photoinitiators do not occur with polymeric ones since polymers are easily miscible with the resin to be cured as well as with the final cured film. Moreover, odor and toxicity problems do not occur with macrophotoinitiators owing to the low volatility of the large molecules. The low migration tendency of polymeric photoinitiators and of photoproducts means that cured coatings are less prone to yellowing (page 5306). Temel et al. further teach the reaction of bisallyl-benzophenone with a dithiol in a thiol-ene polymerization to obtain a polymeric photoinitiator: (Scheme 2 on page 5307). It would have been obvious to one of ordinary skill in the art to react with HS-CH 2 -CH 2 -SH in a thiol-ene polymerization in order to obtain a polymeric photoinitiator with good solubility and miscibility, low odor and toxicity. HS-CH 2 -CH 2 -SH is a polythiol compound B, and the polymeric photoinitiator of Ming modified by Temel is a polyfunctionalized macromolecular photoinitiator prepared from the double bond-containing a -aminoketone photoinitiator A and a polythiol compound B through thiol-ene click reaction. With regard to claims 2 and 3, is a double-bond containing a-aminoketone photoinitiator A wherein R 1 and R 2 are C 1 alkyl groups (methyl groups) , and X is absent. With regard to claims 13-16, Temel et al. teach that the polymeric initiator may be used in an amount of 1wt% in a polymerizable composition and the polymerizable compound represents 10wt% (see figure 7 on page 5310). is sensitive to ultraviolet light and visible light (claim 8 of Ming et al. ). With regard to claim 17, Temel et al. teach the use of the polymeric initiator for the polymerization of HDDA (1,6-hexanediol diacrylate) (see figure 7 on page 5310), which is a monomer. Claim s 7 and 8 are rejected under 35 U.S.C. 103 as being unpatentable over Yamato et al. (EP 1 177 182 B1) in view of Temel et al. (“Synthesis of Main Chain Polymeric Benzophenone Photoinitiator via Thiol-ene Click Chemistry and Its Use in Free Radical Polymerization”) as applied to claim 1 above, and further in view of Toda et al. (US 2016/0145392) and Kapar (US Patent 3,192,224). With regard to claim 7, Yamato modified by Temel teach the photoinitiator in claim 1 (see paragraph 6 above). Temel et al. teach mixing the photoinitiator with unsaturated bonds and a polythiol compound with a molar ratio of unsaturated bonds to thiol groups of 1:1 (see Synthesis of Polymeric Photoinitiator with Thiol-ene Click Chemistry on page 3207 and Scheme 2 on page 5307). AIBN in an amount of 1-2 wt% is added to the mixture, and the reaction takes place at 85 o C for 24 hours under argon atmosphere. The reaction product is isolated by precipitation (see Synthesis of Polymeric Photoinitiator with Thiol-ene Click Chemistry on page 3207). The amount of AIBN and the reaction temperature are within the ranges in claim 7. Temel further teach that IR spectroscopic analysis is used to determine if there are any thiol groups left (right column, page 5309). This meets the limitations of claim 7 for “whether the reaction is completed or not is determined by monitoring an absorption peak of thiol by infrared spectroscopy, and when the absorption peak of thiol is absent, it indicated completion of the reaction”. Yamato et al. and Temel et al. fail to teach nitrogen atmosphere, the reaction temperature, and the recrystallization of the reaction product. However, Toda et al. teach that a thiol-ene reaction may take place under an inert gas atmosphere, such as nitrogen or argon gas (par.0135) , and Kapar teaches that reaction products may be purified by methods such as precipitation or recrystallization (column 3, lines 30-34). Therefore, it would have been obvious to one of ordinary skill in the art before the filing date of the claimed invention to have the thiol-ene reaction of Yamato modified by Temel under nitrogen atmosphere and purify the reaction product by recrystallization. Additionally, it is well-known that a reaction duration may be optimized. With regard to claim 8, is a double-bond containing a -aminoketone photoinitiator A wherein R 1 and R 2 are C 1 alkyl groups , and X is an unsubstituted alkyl group with 1 carbon atom. Claim s 7-9 are rejected under 35 U.S.C. 103 as being unpatentable over Ming et al. (CN 114605572 A, with attached machine translation) in view of Temel et al. (“Synthesis of Main Chain Polymeric Benzophenone Photoinitiator via Thiol-ene Click Chemistry and Its Use in Free Radical Polymerization”) as applied to claim 1 above, and further in view of Toda et al. (US 2016/0145392) and Kapar (US Patent 3,192,224). With regard to claim 7, Ming modified by Temel teach the photoinitiator in claim 1 (see paragraph 8 above). Temel et al. teach mixing the photoinitiator with unsaturated bonds and a polythiol compound with a molar ratio of unsaturated bonds to thiol groups of 1:1 (see Synthesis of Polymeric Photoinitiator with Thiol-ene Click Chemistry on page 3207 and Scheme 2 on page 5307). AIBN in an amount of 1-2 wt% is added to the mixture, and the reaction takes place at 85 o C for 24 hours under argon atmosphere. The reaction product is isolated by precipitation (see Synthesis of Polymeric Photoinitiator with Thiol-ene Click Chemistry on page 3207). The amount of AIBN and the reaction temperature are within the ranges in claim 7. Temel further teach that IR spectroscopic analysis is used to determine if there are any thiol groups left (right column, page 5309). This meets the limitations of claim 7 for “whether the reaction is completed or not is determined by monitoring an absorption peak of thiol by infrared spectroscopy, and when the absorption peak of thiol is absent, it indicated completion of the reaction”. Yamato et al. and Temel et al. fail to teach nitrogen atmosphere, the reaction temperature, and the recrystallization of the reaction product. However, Toda et al. teach that a thiol-ene reaction may take place under an inert gas atmosphere, such as nitrogen or argon gas (par.0135) , and Kapar teaches that reaction products may be purified by methods such as precipitation or recrystallization (column 3, lines 30-34). Therefore, it would have been obvious to one of ordinary skill in the art before the filing date of the claimed invention to have the thiol-ene reaction of Ming modified by Temel under nitrogen atmosphere and purify the reaction product by recrystallization. Additionally, it is well-known that a reaction duration may be optimized. With regard to claims 8 and 9, is a double-bond containing a -aminoketone photoinitiator A wherein R 1 and R 2 are C 1 alkyl groups (methyl groups) , and X is absent. Claims 10 and 11 are rejected under 35 U.S.C. 103 as being unpatentable over Yamato et al. (EP 1 177 182 B1) in view of Temel et al. (“Synthesis of Main Chain Polymeric Benzophenone Photoinitiator via Thiol-ene Click Chemistry and Its Use in Free Radical Polymerization”), Toda et al. (US 2016/0145392) and Kapar (US Patent 3,192,224) as applied to claim 7 above, and further in view of Yang (“Health Safety Research Progress of Photoinitiators”, made of record by the applicant on July 26, 2023). With regard to claim 4, Yamato modified by Temel, Toda and Kapar teach the method of claim 7 (see paragraph 9 above), but fail to teach that the polythiol compound B is a trithiol or tetrathiol. However, Yang teaches that a tetrathiol of formula: may be used in a thiol-ene reaction of with a initiator comprising a double bond in order to obtain a polymeric initiator (see page 108). Therefore, it would have been obvious to one of ordinary skill in the art before the filing date of the claimed invention to use a tetrathiol of formula: as the polythiol in a thiol-ene reaction with of Yamato modified by Temel, Toda and Kapar in order to obtain a polymeric initiator. The tetrathiol above meets the limitations of claim 10. With regard to claim 11, the tetrathiol above is the compound of formula B1. Allowable Subject Matter Claims 6 and 12 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims. Yamato et al. (EP 1 177 182 B1) and Ming et al. (CN 114605572 A) fail to teach the a -aminoketone-containing polyfunctionalized macromolecular photoinitiator in claim 6 and the method in claim 12. There are no prior art teachings that would motivate one of ordinary skill to modify Yamato et al. or Ming et al. and obtain the a -aminoketone-containing polyfunctionalized macromolecular photoinitiator in claim 6 and the method in claim 12 of the instant application. Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to FILLIN "Examiner name" \* MERGEFORMAT ANCA EOFF whose telephone number is FILLIN "Phone number" \* MERGEFORMAT (571)272-9810 . The examiner can normally be reached FILLIN "Work Schedule?" \* MERGEFORMAT Mon-Fri 10am-6:30pm . 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, FILLIN "SPE Name?" \* MERGEFORMAT Niki Bakhtiari can be reached at FILLIN "SPE Phone?" \* MERGEFORMAT (571)272-3433 . 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. /ANCA EOFF/ Primary Examiner, Art Unit 1722
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Prosecution Timeline

Jul 26, 2023
Application Filed
Mar 11, 2026
Non-Final Rejection — §103 (current)

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Prosecution Projections

1-2
Expected OA Rounds
80%
Grant Probability
91%
With Interview (+11.3%)
2y 10m
Median Time to Grant
Low
PTA Risk
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