ityNotice 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
Applicant’s Request for Reconsideration dated September 25, 2025 is acknowledged.
Claims 1, 6, 10, 13, 19-21, 25, 26, 43 and 49-55 are pending.
Claims 2-5, 7-9, 11, 12, 14-18, 22-24, 27-42 and 44-48 are cancelled.
Claims 1, 6 and 10 are currently amended.
Claims 51-55 are new.
Claims 25 and 26 remain withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Claims 1, 6, 10, 13, 19-21, 43 and 49-55 as filed on September 25, 2025 are under consideration.
This action is made FINAL.
37 CFR 1.121 – Manner of Making Amendments
With regard to claims 51-55, as per MPEP § 714 II C (B) any claims added by amendment must be indicated as "new" and the text of the claim must not be underlined.
Withdrawn Objections / Rejections
In view of the amendment of the claims, all previous claim rejections under 35 USC 102 by Browne are withdrawn and all previous claim rejections under 35 USC 103 over Meng are withdrawn.
Applicant’s arguments and the (second) Declaration of Michael Croix have been fully considered. Rejections and/or objections not reiterated from previous office actions are hereby withdrawn. The following rejections and/or objections are either reiterated or newly applied. They constitute the complete set presently being applied to the instant application.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on September 25, 2025 was considered.
Claim Objections
Claims 1, 53 and 54 are objected to because of the following informalities:
Claim 1, clause (a), last three lines: “a concentration of the photochromic dye” is properly “the concentration of the photochromic dye” because antecedent basis is implicit.
Claim 53: “a thickness” is properly “the thickness” and “a diameter” is properly “the diameter”.
Claim 54: “a thickness” is properly “the thickness”.
Appropriate correction is required.
New Grounds of Rejection Necessitated by Amendment
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.
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 1, 6, 10, 13, 19-21, 43 and 49-55 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 pre-AIA the applicant regards as the invention.
Claim 1 as currently amended in clause (a) recites a low vapor pressure at 100 ºC. Low is a relative term which renders the claim indefinite. The term “low” is not defined by the claim, the specification (e.g., page 19, lines 8-10) does not provide a standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the scope of the invention. Claims 6, 10, 13, 19-21, 43 and 49-55 are included in this rejection because they depend from claim 1 and because they do not remedy the noted ambiguity.
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 of this title, 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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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.
Claims 1, 6, 19-21, 43, 49-52 and 55 are rejected under 35 U.S.C. 103 as being unpatentable over Shibahashi et al. (US 2007/0082977, published April 12, 2007) in view of Browne et al. “Oxidative electrochemical switching in dithienylcyclopentenes, Part 1: effect of electronic perturbation on the efficiency and direction of molecular switching,” Chemistry – a European Journal 11:6414-6429, 2005, of record; Sako et al. (JP 08-156479, published June 18, 1996, as evidenced by the Google translation); and Morimitsu et al. (US 2010/0041551, published February 18, 2010).
Shibahashi teaches ink compositions comprising a photochromic agent containing a diarylethene photochromic compound dissolved, dispersed or suspended in a vehicle containing at least a solvent (carrier) and a binder (adhesive) (title; abstract; claims), as required by instant claim 20. The ink develops color by irradiation with UV and can return to the original color by irradiating with visible light (paragraphs [0001], [0008]). Exemplary diarylethene photochromic compounds have a basic skeleton:
PNG
media_image1.png
122
132
media_image1.png
Greyscale
such as:
PNG
media_image2.png
166
168
media_image2.png
Greyscale
which may be fluorinated or perfluorinated, however, the compounds are not limited to these examples (paragraphs [0028]-[0034]). Each group B and C may be:
PNG
media_image3.png
148
236
media_image3.png
Greyscale
(paragraphs [0039], [0040]).
The photochromic agent is a microcapsule pigment in which the diethylene photochromic compound is encapsulated (shell enclosing a cavity) or a resin powder particle (solid, polymer matrix) containing the photochromic compound (physically or chemically) (claim 3; paragraph [0045]). The microcapsule may have a diameter of 0.5 to 50 microns, of 1 to 30 microns (paragraph [0046]; Examples), as required by instant claim 51. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990). See MPEP 2144.05 I. Example 1 is drawn to encapsulation with an epoxy resin (paragraph [0090]). Example 4 is drawn to resin powder particles having an average diameter of 2 microns (paragraph [0104]).
The compositions may further comprise a non-photochromic dye or pigment (claim 4), as required by instant claim 49.
The compositions may further comprise inter alia hydroxyethyl cellulose (paragraphs [0080]-[0082]), as required by instant claims 20, 21.
The compositions may be oil-based or aqueous-based (dermatologically acceptable) (paragraph [0085]).
Regarding the limitation that the shell of embodiment (a) of claims 1 and 52 allows at least 60%, at least 80% transmittance of light in the UV and visible range, because Shibahashi teaches the ink develops color by irradiation with UV and can return to the original color by irradiating with visible light (paragraphs [0001], [0008]), it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention that the shell of the microcapsule pigment must transmit light in the UV and visible range in order reversibly develop color.
Shibahashi does not specifically teach the dye of claims 1, 19, 43, 50.
Shibahashi does not teach microcapsules comprising a cavity in which the dye is suspended in a liquid solvent in a concentration of 0.1 to 10 wt%, the liquid solvent being non-toxic, non-flammable, water immiscible, having a low vapor pressure at 100 ºC, having a boiling point higher than 160 ºC as required by claim 1.
Shibahashi does not teach the shells comprise inter alia cross-linked gelatin as required by claim 6.
Shibahashi does not teach 0.1 to 5 wt% of the dye as required by claim 55.
These deficiencies are made up for in the teachings of Browne, Sako and Morimitsu.
Browne teaches electrochemical switching in dithienylhexahydro- and dithienylhexafluoro- cyclopentenes and exemplifies solutions thereof (title; abstract; Scheme 1; Table 2):
PNG
media_image4.png
244
772
media_image4.png
Greyscale
, as required by instant claim 19. Browne illustrates the UV/Vis absorption spectra of Ho and Hc in Figure 1:
PNG
media_image5.png
730
470
media_image5.png
Greyscale
(“reactive” to UVB over UVA as defined at page 9, lines 24-28 of the instant specification).
Sako teaches a photochromic pen comprising microcapsules comprising a photochromic solution (title; abstract; claims). The solvent for forming the solution is not limited as long as it dissolves the photochromic compound, but a solvent having a boiling point of 40 to 160 ºC is preferable (page 2, 4th full paragraph). The concentration of the photochromic compound in the solution is not limited but is usually 5 to 50 wt% (page 2, 4th full paragraph), as required by instant claim 55. Various materials are used as the capsule, however, a gelatin based film material is preferable; the capsules are prepared via an emulsification process wherein the photochromic solution is emulsified with an aqueous gelatin solution after which a curing agent such as glutaraldehyde is added (cross-linked) (page 2, 6th full paragraph), as required by instant claim 6.
Morimitsu teaches photochromic media comprising diarylethene photochromes (title; abstract; claims; Scheme 1):
PNG
media_image6.png
304
856
media_image6.png
Greyscale
, as required by instant claim 50. The photochrome is dissolved in any suitable carrier such as a solvent such as non-polar hydrocarbon liquids of the ISOPAR series (non-toxic, non-flammable, immiscible with water, low vapor pressure at 100 ºC) having boiling points from about 157 to 329.4 ºC (claims 12, 13; paragraph [0033]). The photochrome solution may be provided in capsules; useful exemplary capsule materials include gelatin (claim 14; paragraph [0046]). The encapsulating material is transparent and colorless, to provide the full effect of the photochrome (paragraph [0046]).
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 photochromic agent of the capsules or/and of the resin particles of the ink compositions of Shibahashi to comprise the photochromic compounds according to Browne inclusive of the of the hexahydro embodiment because simple substitution of functionally equivalent elements yields predictable results, absent evidence to the contrary.
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 capsules of the ink compositions of Shibahashi in view of Browne to comprise 5 to 50 wt% of the photochromic agent dissolved in a solvent having a boiling point of 40 to 160 ºC as taught by Sako because such is suitable for microcapsules suitable for including within ink compositions. There would be a reasonable expectation of success because Shibahashi embraces any microcapsule pigment.
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 solvent of the core of the capsules of the ink compositions of Shibahashi in view of Browne and Sako to comprise solvents inclusive of non-polar hydrocarbon liquids of the ISOPAR series (non-toxic, non-flammable, immiscible with water, low vapor pressure at 100 ºC) as taught by Morimitsu because these solvents are suitable for diarylethene photochromes inclusive of the photochromes of Browne.
Regarding the limitation that the shell of embodiment (a) of claims 1 and 52 allows at least 60%, at least 80% transmittance of light in the UV and visible range, although Shibahashi renders transmission obvious, in the alternative, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention that the shell of the capsules of the ink compositions of Shibahashi in view of Browne, Sako and Morimitsu should be transparent and colorless as taught by Morimitsu in order to provide the full effect of the photochrome.
Regarding the property of UVB selectivity as required by claim 1, "[p]roducts of identical chemical composition can not have mutually exclusive properties." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). See MPEP 2112. In further support of this presumption, Browne illustrates the UVB selectivity of the instantly claimed dye. Alternatively, because the combined teachings of the prior art render obvious the ink compositions instantly claimed, it necessarily follows that the instantly claimed dye within the compositions rendered obvious by the combined teachings of the prior art must also possess a UVB selectivity at least 10 times more than for UVA.
Regarding claim 6, 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 shell of the capsules of the ink compositions of Shibahashi in view of Browne, Sako and Morimitsu to comprise crosslinked gelatin as taught by Sako because such is suitable for encapsulating photochromic agents and because Morimitsu exemplifies gelatin as a suitable transparent shell material.
Regarding the property of claim 43 drawn to ring-closure isomerization, "[p]roducts of identical chemical composition can not have mutually exclusive properties." In further support of inherency, page 13, line 12 through page 15, line 11 of the instant specification evidence diarylethene compounds of Formula (II) are temperature independent dyes, the color of which can be calibrated by the specific functional groups A, B and R5 and R6 .
Regarding the properties of claim 50, "[p]roducts of identical chemical composition can not have mutually exclusive properties." In further support of inherency, Morimitsu evidences the diarylethene photochrome instantly claimed is colorless in the absence of UV radiation in scheme 1.
Claims 1 and 10 rejected under 35 U.S.C. 103 as being unpatentable over Shibahashi et al. (US 2007/0082977, published April 12, 2007) in view of Browne et al. “Oxidative electrochemical switching in dithienylcyclopentenes, Part 1: effect of electronic perturbation on the efficiency and direction of molecular switching,” Chemistry – a European Journal 11:6414-6429, 2005, of record; Sako et al. (JP 08-156479, published June 18, 1996, as evidenced by the Google translation); and Morimitsu et al. (US 2010/0041551, published February 18, 2010) as applied to claims 1, 6, 19-21, 43, 49-52 and 55 above, and further in view of Pagba et al. (WO 2013/138796, published September 19, 2013).
Pagba is applied herewith on alternative embodiment (b)
The teachings of Shibahashi, Browne, Sako and Morimitsu have been described supra.
They do not teach polymers having a glass transition temperature below 25 ºC as required by claim 1.
They do not teach a polysiloxane as required by claim 10.
These deficiencies are made up for in the teachings of Pagba.
Pagba teaches silicone material having a photochrome additive; the silicone may be a silicone rubber or a polydimethylsiloxane (PDMS) (title; abstract; claims; paragraphs [0018], [0021]). Silicones can be flexible, having rubber like properties (Tg below 25 ºC) (paragraph [0006]). Silicones are largely UV resistant, meaning they can withstand long exposures to UV without degrading; this contrasts with many plastics (paragraph [0007]). PDMS is optically clear (paragraph [0029]).
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 resin of the resin particles of the ink compositions of Shibahashi or/and of Shibahashi in view of Browne to comprise a silicone material as taught by Pagba because silicones can be flexible, are largely UV resistant and are optically clear. There would be a reasonable expectation of success because silicone is a species of resin falling within the genus embraced by Shibahashi.
Claim 13 is rejected under 35 U.S.C. 103 as being unpatentable over Shibahashi et al. (US 2007/0082977, published April 12, 2007) in view of Browne et al. “Oxidative electrochemical switching in dithienylcyclopentenes, Part 1: effect of electronic perturbation on the efficiency and direction of molecular switching,” Chemistry – a European Journal 11:6414-6429, 2005, of record; Sako et al. (JP 08-156479, published June 18, 1996, as evidenced by the Google translation); and Morimitsu et al. (US 2010/0041551, published February 18, 2010) as applied to claims 1, 6, 19-21, 43, 49-52 and 55 above, and further in view of Ercole et al. “Optimizing the photochromic performance of naphthopyrans in a rigid host matrix using poly(dimethylsiloxane) conjugation,” Journal of Materials Chemistry 19:5612-5623, 2009, of record.
The teachings of Shibahashi, Browne, Sako and Morimitsu have been described supra.
They do not teach oligomer conjugation as required by claim 13.
This deficiency is made up for in the teachings of Ercole.
Ercole teaches photochemical behavior of photochromic molecules is profoundly influenced by the media in which they are incorporated; rigid media restrict the movement of the photochromic molecules thereby hindering photochromic switching (page 5612, rhc, full paragraph). Covalent attachment of oligomers directly to the dye alters the local environment and encapsules the dye within aggregates thereby improving molecular mobility and switching; attachment of PDMS (poly(dimethylsiloxane)) oligomers manifests a strong lubricating effect by introducing a local environment of low viscosity and higher mobility, effectively improving switch mobility (paragraph bridging pages 5612-5613). The oligomers have an average molecular weight of about 1200 g/mole (page 5618, lhc).
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 photochromic agent of the ink compositions of Shibahashi in view of Browne, Sako and Morimitsu to further comprise PDMS oligomers covalently attached thereto as taught by Ercole because the attachment of PDMS oligomers manifests a strong lubricating effect by introducing a local environment of low viscosity and higher mobility, effectively improving switch mobility.
Claims 53 and 54 are rejected under 35 U.S.C. 103 as being unpatentable over Shibahashi et al. (US 2007/0082977, published April 12, 2007) in view of Browne et al. “Oxidative electrochemical switching in dithienylcyclopentenes, Part 1: effect of electronic perturbation on the efficiency and direction of molecular switching,” Chemistry – a European Journal 11:6414-6429, 2005, of record; Sako et al. (JP 08-156479, published June 18, 1996, as evidenced by the Google translation); and Morimitsu et al. (US 2010/0041551, published February 18, 2010) as applied to claims 1, 6, 19-21, 43, 49-52 and 55 above, and further in view of Michael (EP 376,385, published July 4, 1990).
The teachings of Shibahashi, Browne, Sako and Morimitsu have been described supra.
Shibahashi does not teach the thickness of the shell is less than 10% of the diameter of the microcapsules as required by claim 53.
Shibahashi does not teach the thickness of the shell is 200 nm to 5 microns as required by claim 54.
These deficiencies are made up for in the teachings of Michael.
Micheal teaches perfume microcapsules having an average size from 5 to 500 microns, a liquid core, a solid thin polymeric shell having an average thickness of 0.1 to 50 microns and comprising gelatin (title; abstract; claims, in particular 1, 2).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention that the thickness of the shell of the capsules of the ink compositions of Shibahashi in view of Browne, Sako and Morimitsu is less than 50% of the diameter of the capsules as a matter of geometric necessity and it would have been obvious that that gelatin shells encapsulating an oily core may have a minimal thickness of about 0.1 microns as taught by Michael and a maximal thickness of about 50% of the diameter of 0.5 to 50 microns embraced by Shibahashi.
Response to Arguments and Declaration: Claim Rejections - 35 USC § 103
Applicant’s arguments and the (second) Declaration have been fully considered but they are substantially moot in light of the new grounds of rejection applied infra as necessitated by Applicant’s amendments.
Applicant’s position at pages 8 and 13-14 of the Remarks that Browne does not disclose a photochromic dye that is at least 10 times more reactive to UVB to UVA remains unpersuasive because Browne indisputably discloses the same photochromic dye as instantly claimed. To the extent that Applicant cites to the UV-Vis spectrum of Browne, the UV-Vis spectrum of Figure 7 of the instant specification also does not meet the claimed property, nor is there any disclosure within the instant specification demonstrating Applicant to be in possession of that which is claimed or guiding the ordinary artisan how to formulate DTE in order to achieve the newly claimed property. The (second) Declaration and Exhibit A thereof also does not demonstrate DTE possesses the newly claimed property, however, item 5 states the contrary. Therefore, for purposes of the instant Office Action the newly claimed property is presumed to be a property of DTE.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Nakanishi et al. (US 5,017,225, IDS reference filed July 20, 2021) teaches microencapsulated photochromic material and water-based ink compositions thereof (title; abstract; claims). The photochromic material is encapsulated as a solution comprising a solvent having boiling point of 40 to 160 ºC and a solubility in water at 20 ºC of 15 wt% or below (claim 2). The microcapsules consist of a crosslinked gelatin film agent (claim 3).
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ALISSA PROSSER whose telephone number is (571)272-5164. The examiner can normally be reached M - Th, 10 am - 6 pm.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, DAVID BLANCHARD can be reached on (571)272-0827. 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.
/ALISSA PROSSER/
Examiner, Art Unit 1619
/DAVID J BLANCHARD/Supervisory Patent Examiner, Art Unit 1619