DETAILED ACTION
This office action follows a reply filed on April 27, 2026. Claim 16 has been amended. Claims 16, 20 and 32-33 are currently pending and under examination.
The texts of those sections of Title 35 U.S. Code are not included in this section and can be found in a prior Office action.
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claim Rejections - 35 USC § 103
Claims 16, 20 and 32-33 are rejected under 35 U.S.C. 103 as being unpatentable over WO 2016/193237, in view of JP 2018-048217 and JP 2017-141387, and further in view of Reichert (US 2017/0051166).
WO ‘237 teaches the following:
PNG
media_image1.png
276
308
media_image1.png
Greyscale
PNG
media_image2.png
58
614
media_image2.png
Greyscale
PNG
media_image3.png
160
596
media_image3.png
Greyscale
When n=3, X=O-C2H4-O-C2H4-O-C2H4-O-CH3. This meets applicants’ claimed formula (Ib) when R16 is (CH2CH2O)n1CH2CH2R19, when n1=2 and R19 is OCH3.
WO ‘237 teaches the claimed pigments for use in a solvent based printing ink, teaching the mean particle size as 15-1000 nm, but does not teach the claimed particle size distribution or D90, as claimed.
JP ‘217 teaches kneading and polishing an infrared absorber so that the average particle size is 10-100 nm, preferably 30-60 nm, teaching that when the size is less than 100 nm, the visible transparency is excellent, but if the particle size is too small, the dispersion stability in the solvent will be deteriorated (p. 8). Salt milling by way of a kneader is taught as a suitable method for adjusting the particle size of the infrared absorber. The average particle size of JP ‘217 is described as the 50% diameter, where the average particle size is measured as the arithmetic average of the primary particle diameters for 400 primary particles (p. 39). JP ‘217 does not limit the type of near-infrared absorbing organic pigment and teaches that they include naphthalocyanine compounds (p. 24).
As to the D90, JP ‘387 teaches an ink composition and teaches that when the D90 is less than 100 nm, the aggregation tendency of a pigment can be further reduced, and storage stability and ejection stability of the ink are further improved. Salt milling by way of a kneader is described as a possible method for reducing the particle size.
Therefore, preparing the pigments of WO ‘237 to have an average particle size of 20-60 nm and a D90 of less than 100 nm is prima facie obvious.
As to the standard deviation, JP ‘217 teaches a coefficient of variation of preferably 20-30%, which is determined by the following: (standard deviation/arithmetic average value)x100 (p. 8). A pigment with a particle size of 20-60 nm and a coefficient of variation of 20-30% results in a standard deviation of 4-18 nm, which is much less than the claimed 25 nm.
Reichert exemplifies Ga-naphthalocyanine chromophores with short chain alkoxy axial substituents, and their use as almost colorless IR absorbers for optical filter applications (Abstract). Reichert exemplifies preparing Propoxy-Ga Naphthalocyanine and Butoxy-Ga-naphthalocyanine, which are subject to pigment finishing methods, such as kneading, teaching that when the pigment is subjected to pigment finishing, the remission values are reduced, which as evidenced by the instant specification, is an indication of higher IR absorbance, providing additional motivation to subject the naphthalocyanines of WO ‘237 to pigment finishing methods such as kneading, as WO ‘237 clearly desires a high IR absorbance.
Therefore it would have been obvious to one of ordinary skill in the art at the time the invention was filed to have carried out pigment finishing techniques on the pigments of WO ‘237, as Reichert teaches that these can provide a pigment with a higher IR absorbance.
WO ‘237 in view of JP ‘217, ‘387 and further in view of Reichert is prima facie obvious over instant claims 16 and 32-33.
As to claim 20, WO ‘237 teaches that the metal center of the naphthalocyanine can be Ga-O(C2H4O)nCH3, where n=1-6. When n=1, Ga-O-C2H4-OCH3 is present and meets applicants’ compound 1a.
Response to Arguments
Applicant's arguments filed April 27, 2026 have been fully considered but they are not persuasive.
Applicants argue unexpected results when using particles with the claimed “finely tuned” particle size.
Applicants have not shown the criticality of the claimed range, by showing the effects of the particle sizes inside and outside of the claimed range, as applicants have only prepared one example that falls within the claimed scope of the invention and compared it to only one example outside of the claimed range.
MPEP 716.02(d) Unexpected Results Commensurate in Scope with Claimed Invention: “…the showing of unexpected results must be reviewed to see if the results occur over the entire range.”
Applicants argue that the effect provided by the claimed particles is not merely a result of routine optimization.
The examiner did not argue routine optimization, as three supporting references are provided above to give motivation to choose the claimed particle size.
Applicants argue that JP '217 does not relate to gallium phthalocyanine compounds.
JP '217 teaches producing a pigment dispersion, where a near-infrared organic pigment is kneaded and polished, where JP '217 specifically teaches the near-infrared organic pigment to include any organic pigment having a maximum absorption wavelength in the near-infrared region, and lists naphthalocyanine compounds as suitable near-infrared organic pigments (p. 4).
Applicants have not provided any evidence that the claimed particle size is only critical for the claimed pigments and not any organic pigment having a maximum absorption wavelength in the near-infrared region, as suggested by JP ‘217.
Applicants argue that JP ‘217 states the average particle size is 10-100 nm, and teaches a coefficient of variation of 20-30%, but then states that “concrete values for average particle size, standard deviation, and D90 are missing.”
JP ‘217 teaches average particle size and a coefficient of variation, which can be used to calculate the standard deviation. D90 is taught by JP ‘387.
Applicants argue that JP ‘387 does not relate to the claimed pigments.
The pigments of both JP ‘387 and WO ‘237 are both insoluble in the solvent medium, both used for printing inks, and WO ‘237 teaches that the pigments can be used in oil-based printing inks, which are similarly used in JP ‘387. JP ‘387 does not limit the pigments to only those listed, and one of ordinary skill in the art would expect the claimed pigment with the claimed D90 to possess a reduction in aggregation and an improvement in stability, as suggested by JP ‘387.
Applicants argue that JP ‘983 does not teach the claimed particles size; however, this reference was not used in the above rejection.
Applicants argue that Reichert teaches Ga-naphthlocyanines with short alkoxy axial substituents, which are not within the scope of the pending claims.
While the examiner agrees, the compounds of Reichert are in the same field of endeavor and shows that by carrying out a pigment finishing method, such as kneading or milling, the remission values are reduced. Note that Reichert is a common inventor with WO '237. JP '217 teaches the method of kneading and milling. Reichert provides additional motivation for carrying out the method of kneading of JP '217, as the remission values of the near infrared absorbing pigment would be expected to be reduced, which is evidenced of a higher absorbance, which would similarly be desired by WO '237.
Conclusion
THIS ACTION IS MADE FINAL. 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 BRIEANN R JOHNSTON whose telephone number is (571)270-7344. The examiner can normally be reached Monday-Friday, 8:00 AM - 4:00 PM EST.
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, Randy Gulakowski can be reached at (571)272-1302. 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.
/Brieann R Johnston/Primary Examiner, Art Unit 1766
Prosecution Insights