DETAILED ACTION
1. The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
2. This application is a 371 of App. No. PCT/US2022/019699, filed on 03/10/2022, which is entitled to and claims the benefit of priority of U.S. Provisional App. No. 63/158,929, filed 03/10/2021. The preliminary amendment filed on 12/08/2025 is entered and acknowledged by the Examiner.
3. Applicant’s election of Group I, claims 1-18 with traverse in the reply filed on 12/08/2025 is acknowledged. The traversal is on the ground that claims 19, and 28-32, 34 depend directly or indirectly from independent claim 1, therefore, claims 19, and 28-32, 34 should also be considered to be part of Group I, since it would not be unduly burdensome for the examiner to search and examine both groups of claims. This is not found persuasive because the claims are directed to different inventions, and the inventions of claim 19, and claims dependent thereon have acquired a separate status in the art due to its recognized divergent subject matter as stated in the restriction requirement of 10/06/2025, and furthermore the invention requires a different field of search, for example, searching different classes/subclasses or electronic resources, or employing different search queries and as such examination of both sets of claims would necessarily be different. Examination and prosecution of two different inventions would in fact pose an undue burden on the examiner. However, claims 19, and 28-32, 34 will be rejoined upon the allowable Group I (i.e., claims 1-18).
4. Claims 1-19, 28-32, 34 are pending. Claims 1-18 are under examination on the merits. Claims 19, 28 are amended. Claims 20-27, 33, 35 are cancelled. Claims 36-45 are previously cancelled. Claims 19, 28-32, 34 are withdrawn to a non-elected invention from further consideration.
Information Disclosure Statement
5. The information disclosure statement submitted on 09/08/2023 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the examiner has considered the information disclosure statement.
Drawings
6. The drawings are received on 09/08/2023. These drawings are acceptable.
Priority
7. Receipt is acknowledged of papers submitted on 09/08/2023 under 35 U.S.C. 119(a)-(d), which papers have been placed of record in the file.
Claim Rejections - 35 USC § 102
8. 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.
9. Claims 1-4, 11, 18 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Shah et al. (Viologen-Based Electrochromic Materials: From Small Molecules, Polymers and Composites to Their Applications, hereinafter “Shah”).
Regarding claim 1: Shah discloses a composite composition (Page 12, viologen based composite materials, 3rd para) comprising: one or more chromogenic (Page 12, 3rd para, chromophore) thiazolothiazoles (Page 6, Fig. 5, structure labeled MV2; Page 6, 1st para, thiazolothiazole bridged viologens MV2) contained in an aqueous-based (Page 16, Fig. 15 showing the viologen in an aqueous solution in the device) polyelectrolyte matrix (Page 19, 2nd para, gel/ionic liquid based electrolytes were successfully employed; Page 2, Fig. 1, showing the basic scheme of the electrochromic device wherein the viologen is contained in between the electrodes; Page 5, 2nd para, single layer all in one ECO with a polymer gel electrolyte).
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Regarding claim 2: Shah discloses the composite composition (Page 12, viologen based composite materials, 3rd para), wherein the one or more chromogenic thiazolothiazoles are soluble in the aqueous-based polyelectrolyte matrix (Page 3, 2nd para, bipyridilium viologens are soluble in the colorless state).
Regarding claim 3: Shah discloses the composite composition (Page 12, viologen based composite materials, 3rd para), wherein the one or more chromogenic thiazolothiazoles include a thiazolo(5,4-d)thiazole heterocycle structure (Page 6, Fig. 5, structure labeled MV2).
Regarding claim 4: Shah discloses the composite composition (Page 12, viologen based composite materials, 3rd para), wherein the one or more chromogenic thiazolothiazoles comprise at least two pyridinium moieties (Page 6, Fig 5, structures of various viologen derivatives with a bridging group or a spacer between two pyridyl groups).
Regarding claim 11: Shah discloses the composite composition (Page 12, viologen based composite materials, 3rd para), wherein the one or more chromogenic thiazolothiazoles are symmetric (Page 6, Fig. 5, structure labeled MV2).
Regarding claim 18: Shah discloses the composite composition (Page 12, viologen based composite materials, 3rd para), wherein the one or more chromogenic thiazolothiazoles are at least one of electrochromic, electrofluorochromic, and photochromic (Page 18, 2nd para, electrochromism using Type II material which is a thiazolothiazole as in examples shown in Figure 5).
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Claim Rejections - 35 USC § 103
10. 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.
11. Claims 5-10 are rejected under 35 U.S.C. 103 as being unpatentable over Shah et al. (Viologen-Based Electrochromic Materials: From Small Molecules, Polymers and Composites to Their Applications, hereinafter “Shah”) as applied to claim 1 above, and further in view of Zhi et al. (US Pub. No. 2020/0328479 A1, hereinafter “Zhi”).
Regarding claim 5: The disclosure of Shah is adequately set forth in paragraph 9 above and is incorporated herein by reference. Shah does not expressly teach the aqueous-based polyelectrolyte matrix comprises a hydrogel.
However, Zhi teaches an energy storage device (Page 1, [0001]) that has an active layer between two electrodes (Page 2, [0044], Fig. 1, part labeled 106 sandwiched between electrodes labeled 102 and 104; Page 3, [0091]); wherein the electrolyte is a polymer electrolyte (Page 4, [0100], polymeric electrolyte) wherein the polymeric electrolyte is a hydrogel (Page 2, [0047], hydrogel electrolyte for use in device) with benefit of providing a highly flexible polymeric electrolyte, which may be used in different energy conversion and storage devices (Page 3, [0089]).
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In an analogous art of the gel electrolyte in the making of energy storage device, and in the light of such benefit before the effective filing date of the claimed invention, it would have been obvious to a person of ordinary skill in the art to modify the aqueous-based polyelectrolyte matrix by Shah , so as to include the aqueous-based polyelectrolyte matrix comprises a hydrogel as taught by Zhi, and would have been motivated to do so with reasonable expectation that this would result in providing a highly flexible polymeric electrolyte, which may be used in different energy conversion and storage devices as suggested by Zhi (Page 3, [0089]).
Regarding claim 6: Shah teaches the composite composition (Page 12, viologen based composite materials, 3rd para), wherein the one or more chromogenic thiazolothiazoles are soluble in the aqueous-based phase of the hydrogel (Page 6, 2nd para, bipyridinium viologens are soluble in the colorless state).
Regarding claim 7: Shah teaches the composite composition (Page 12, viologen based composite materials, 3rd para), wherein the one or more chromogenic thiazolothiazoles are incorporated into polyelectrolyte of the hydrogel (Page 10, 2nd para, method of integration of viologens into the polymer main chain).
Regarding claim 8: Shah teaches the composite composition (Page 12, viologen based composite materials, 3rd para), wherein the one or more chromogenic thiazolothiazoles are incorporated into the polyelectrolyte backbone (Page 10, 2nd para, method of integration of viologens into the polymer main chain).
Regarding claim 9: Shah teaches the composite composition (Page 12, viologen based composite materials, 3rd para), wherein the one or more chromogenic thiazolothiazoles are incorporated as side chains of the polyelectrolyte (Page 9, 2nd para, incorporation of the viologen units to the side chain as a pendant).
Regarding claim 10: Shah teaches the composite composition (Page 12, viologen based composite materials, 3rd para), wherein the one or more chromogenic thiazolothiazoles are crosslinkers in the hydrogel (Page 9, 3rd para, thiophene backbone can be crosslinked with the viologens).
12. Claim 12 is rejected under 35 U.S.C. 103 as being unpatentable over Shah et al. (Viologen-Based Electrochromic Materials: From Small Molecules, Polymers and Composites to Their Applications, hereinafter “Shah”) as applied to claim 1 above, and further in view of
Sayresmith et al. (Photostable Voltage-Sensitive Dyes Based on Simple, Solvatofluorochromic, Asymmetric Thiazolothiazoles, J. Am. Chem. Soc. 2019, 141, 18780−18790, hereinafter “Sayresmith”).
Regarding claim 12: The disclosure of Shah is adequately set forth in paragraph 9 above and is incorporated herein by reference. Shah does not expressly teach the one or more chromogenic thiazolothiazoles are asymmetric.
However, Sayresmith teaches the use of asymmetric thiazolothiazoles as solvato fluorochromic voltage sensitive dyes (Page 18780, title) for use as light harvesting dyes (Page 18780, right Col., lines 1-8) with benefit of providing the asymmetric thiazolo[5,4-d]thiazole
TTz derivatives to exhibit strong solvatofluorochromism with Stokes shifts between 0.269
and 0.750 eV (2270 and 6050 cm−1) and transition dipole moments (Δμ = 13−18 D) that are among the highest reported for push−pull dyes (Page 18780, Abstract, lines 10-13).
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In an analogous art of the composite chromogenic composition, and in the light of such benefit before the effective filing date of the claimed invention, it would have been obvious to a person of ordinary skill in the art to modify the chromogenic thiazolothiazoles by Shah, so as to include the one or more asymmetric chromogenic thiazolothiazoles as taught by Sayresmith, and would have been motivated to do so with reasonable expectation that this would result in providing the asymmetric thiazolo[5,4-d]thiazole (TTz) derivatives to exhibit strong solvatofluorochromism with Stokes shifts between 0.269 and 0.750 eV (2270 and 6050 cm−1) and transition dipole moments (Δμ = 13−18 D) that are among the highest reported for push−pull dyes as suggested by Sayresmith (Page 18780, Abstract, lines 10-13).
13. Claims 13-15 are rejected under 35 U.S.C. 103 as being unpatentable over Shah et al. (Viologen-Based Electrochromic Materials: From Small Molecules, Polymers and Composites to Their Applications, hereinafter “Shah”) as applied to claim 1 above, and further in view of
Woodward et al. (Thiazolothiazole Fluorophores Exhibiting Strong Fluorescence and Viologen-Like Reversible Electrochromism, J. Am. Chem. Soc. 2017, 139, 8467−8473, hereinafter “Woodward”).
Regarding claim 13: The disclosure of Shah is adequately set forth in paragraph 9 above and is incorporated herein by reference. Shah does not expressly teach the one or more chromogenic thiazolothiazoles undergoes a first color change in response to a first electron reduction, and a second color change in response to a second electron reduction.
However, Woodward teaches the use of thiazothiazoles (Page 8467, lines 1-2) that display a first color change in response to a first electron reduction(Page 8471, Fig. 4, showing a first color for state TTz2+), and a second color change in response to a second electron
reduction (Page 8471, Fig. 4, showing a first color for state TTz1+) with benefit of providing the planar thiazolothiazole backbone exhibits good electronic communication as evidenced by two reduction peaks. These compounds show their usefulness as multifunctional, π-conjugated electron acceptor materials (Page 8471, right Col., 2nd para, lines 9-12).
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In an analogous art of the composite chromogenic composition, and in the light of such benefit before the effective filing date of the claimed invention, it would have been obvious to a person of ordinary skill in the art to modify the chromogenic thiazolothiazoles by Shah, so as to include the one or more chromogenic thiazolothiazoles undergoes a first color change in response to a first electron reduction, and a second color change in response to a second electron reduction as taught by Woodward, and would have been motivated to do so with reasonable expectation that this would result in providing the planar thiazolothiazole backbone by exhibiting good electronic communication as evidenced by two reduction peaks. These compounds show their usefulness as multifunctional, π-conjugated electron acceptor materials as suggested by Woodward (Page 8471, right Col., 2nd para, lines 9-12).
Regarding claim 14: The disclosure of Shah in view of Woodward is adequately set forth in paragraph 9 above and is incorporated herein by reference. Woodward teaches the first and second color changes are reversible via oxidation (Page 8470, right Col., 2nd para, lines 1-17; (Page 8471, Fig. 4).
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Regarding claim 15: The disclosure of Shah in view of Woodward is adequately set forth in paragraph 9 above and is incorporated herein by reference. Woodward teaches the first and second color changes occur in the visible region of the electromagnetic spectrum.
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14. Claims 16-17 are rejected under 35 U.S.C. 103 as being unpatentable over Shah et al. (Viologen-Based Electrochromic Materials: From Small Molecules, Polymers and Composites to Their Applications, hereinafter “Shah”) as applied to claim 1 above, and further in view of Alesanco et al. (US Pub. No. 2018/0371310 A1, hereinafter “Alesanco”).
Regarding claims 16-17: The disclosure of Shah is adequately set forth in paragraph 9 above and is incorporated herein by reference. Shah does not expressly teach the composite composition further comprising a redox complimentary component, wherein a ratio of the chromogenic thiazolothiazoles to the redox complimentary component ranges from 1:0.1 to 1:5.
However, Alesanco teaches a multichromic composition comprising: (a) a viologen compound of formula (I) as set forth. (b) a polymeric matrix comprising a crosslinked polymer, (c) a redox pair, and (d) a solvent, the compound of formula (I) and the redox pair being embedded in the polymeric matrix (Page 1, [0008]; Page 15, Claim 1). Alesanco teaches
the composition further comprising a redox complimentary component such as ferro/ferricyanide potassium pair, wherein a ratio of the a viologen compound of formula (I) to the redox complimentary component ranges from 1:0.1 to 1:5 (Page 11, [0147]) with benefit of providing
the multichromic composition showing a short switching time and low transmission in the most visible range, which makes it effective in blocking the whole visible radiation in smart windows (Page 1, [0008]-[0010]).
In an analogous art of the composite chromogenic composition, and in the light of such benefit before the effective filing date of the claimed invention, it would have been obvious to a person of ordinary skill in the art to modify the composite composition by Shah, so as to include
the composite composition further comprising a redox complimentary component, wherein a ratio of the chromogenic thiazolothiazoles to the redox complimentary component ranges from 1:0.1 to 1:5 as taught by Alesanco, and would have been motivated to do so with reasonable expectation that this would result in providing the multichromic composition showing a short switching time and low transmission in the most visible range, which makes it effective in blocking the whole visible radiation in smart windows as suggested by Alesanco (Page 1, [0008]-[0010]).
Examiner Information
15. Any inquiry concerning this communication or earlier communications from the examiner should be directed to Bijan Ahvazi, Ph.D. whose telephone number is (571) 270-3449. The examiner can normally be reached on Mon-Fri 9.00 A.M. -7 P.M..
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Joseph Del Sole can be reached on 571-272-1130. 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.
/Bijan Ahvazi/
Primary Examiner, Art Unit 1763
12/17/2025
bijan.ahvazi@uspto.gov
Prosecution Insights