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 .
Response to Amendment
Claim 1 has been amended to narrow the range of the content of a monomer unit according to formula (1) in the vinyl resin; widen the range of the loss elastic modulus G”; and to reflect the limitation of Claim 9, which is accordingly canceled. New Claim 11 has been added. Claims 1, 2, 4 – 7, 10, and 11 are pending in the present application. No new subject matter has been added.
Response to Arguments
Applicant's arguments filed 2026-05-26 have been fully considered but they are not persuasive.
Applicant argues that the invention as described by the presently amended claims is not obvious over the combination of Matsushima, Washino, Hashimoto, and Kadonome, cited in the previous office action (non-final rejection dated 2026-02-24), since Matsushima does not teach a hybrid resin in which a vinyl resin and a polyester resin are bonded. However, as discussed in the treatment of Claim 9 in the previous office action, and in the updated rejection below, that deficiency is remedied by Hashimoto.
Applicant also argues that the hybrid resin of the present invention is not taught by Sugawara (cited in combination with Washino in the previous office action), since Sugawara does not disclose a preparative example of a hybrid resin having a monomer unit derived from lauryl (meth)acrylate. However, the disclosure of a preparative example is not required for the teaching of a prior art reference to be understood by a person of ordinary skill in the art. Applicant also asserts that Sugawara does not disclose a preferred content of (meth)acrylate monomers in the styrene-acrylic segment of the hybrid resin, or the monomer units comprised in the crystalline polyester resin. However, the treatment of Sugawara in the previous office action points out those very teachings by Sugawara, and they are repeated in the updated rejection below.
Finally, Applicant argues that the invention as described by the presently amended claims achieves unexpected results in the evaluations of low-temperature fixability, heat-resistant storability, the number of prints before appearance of streaks in durability testing, and fogging after durability testing. However, as pointed out in Applicant’s remarks, only instant Example 5 satisfies all requirements of amended Claim 1.
From MPEP 716.02(d):
II. DEMONSTRATING CRITICALITY OF A CLAIMED RANGE
To establish unexpected results over a claimed range, applicants should compare a sufficient number of tests both inside and outside the claimed range to show the criticality of the claimed range. In re Hill, 284 F.2d 955, 128 USPQ 197 (CCPA 1960).
A single preparative example satisfying the claim limitations is not sufficient (that is, not a sufficient number of tests inside the claimed range) to show criticality of those limitations.
In addition, as discussed in the previous office action, Matsushima teaches the control of several toner parameters aimed at improving low-temperature fixability and improving thermal-resistant storage property. Kadonome teaches the improvement of cleaning properties of the toner. As also discussed in that office action, several examples from Table 5 of the instant application achieve suppression of fogging following a durability test, despite not possessing all the features of Claim 1. Therefore, the results achieved by the present invention do not represent unexpected results.
For these reasons, the updated rejections below are not withdrawn.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
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, 2, 4, 5, and 11 are rejected under 35 U.S.C. 103 as being unpatentable over Matsushima et al (US PGP 2019/0094732) in view of Washino (US PGP 2019/0056678), further in view of Hashimoto et al (US PGP 2021/0181647).
Matsushima teaches a toner comprising a binder resin, which contains a polyester resin and a vinyl resin ([0009]). Matsushima teaches that the binder resin preferably contains an amorphous polyester resin as a main component (meaning greater than 50% by mass) ([0073]). Matsushima teaches phthalic acid, isophthalic acid, and terephthalic acid as polyvalent carboxylic acids which may be used as monomers in the amorphous polyester ([0078]). In addition, Matsushima teaches bisphenol A (BPA) and ethylene oxide or propylene oxide adducts thereof as polyvalent alcohols which may be used as monomers in the amorphous polyester ([0083]). Both of these groups constitute monomers having a cyclic structure. Matsushima teaches that the weight-average molecular weight of the amorphous polyester resin is preferably 5,000 – 100,000 ([0088]). The amorphous polyester of Matsushima, being the main component of the binder resin and having a cyclic structure, would therefore constitute at least 51% by mass of the THF-soluble fraction of the toner having a molecular weight of at least 2,000. Matsushima teaches that the vinyl resin is preferably a styrene-acrylic resin ([0039]), and gives several examples of styrenes as monomers ([0042]). Also taught are alkyl (meth)acrylates, and lauryl (meth)acrylate is specifically pointed out ([0044]), reading on formula (1) of the instant application.
Matsushima teaches that the binder resin of the toner may contain a crystalline polyester resin in addition to the amorphous polyester ([0069] – [0070]). Matsushima also teaches a preference for inclusion of a crystalline polyester resin ([0093]). In describing diols that may be used to form the crystalline polyester resin, Matsushima teaches ethylene glycol ([0100]), which results in a monomer unit of formula (A) of Claim 1. In describing dicarboxylic acids that may be used to form the crystalline polyester, Matsushima teaches succinic, adipic, pimelic, azelaic, sebacic, nonane dicarboxylic, dodecanedioic, undecane dicarboxylic, and dodecane dicarboxylic acids ([0097]), all of which read on formula (B) of Claim 1.
Matsushima teaches a preferred circularity of the toner of 0.92 – 1.00 ([0166]), encompassing the range stated in Claim 1. The optionality of a core-shell structured toner is taught ([0155]), but Matsushima does not appear to teach a preferred material for a shell layer.
Washino teaches a toner having a core-shell structure ([0012]). Washino teaches that the shell layer preferably contains a thermosetting resin, from the viewpoint of making the shell sufficiently hard ([0035]). Particular preference is given to a thermosetting resin which is a vinyl copolymer containing at least 2-vinyl-2-oxazoline and related derivatives ([0036]). Such a resin would constitute a vinyl resin having an oxazoline group.
Neither Matsushima nor Washino appears to teach preferred contents for the various monomers which make up the vinyl resin.
Hashimoto teaches a toner having a binder resin, which comprises a first crystalline resin and a second amorphous resin (Abstract). The second amorphous resin may be a vinyl resin or a vinyl-hybrid resin ([0125]). Hashimoto further teaches that the content of such a resin should not be more than 70% by mass ([0130]), allowing the hybrid resin to represent the main component of the toner particle. Hashimoto teaches monomers which may be incorporated into the amorphous vinyl resin, which include styrenes ([0133]) and acrylates, including dodecyl (lauryl) acrylate ([0134]). In describing the styrene-based monomers which may be contained in the vinyl resin, Hashimoto teaches that their content should not exceed 95% by weight of the vinyl resin monomers ([0149]), allowing the content of a styrene monomer unit in the vinyl resin to encompass the range stated in Claim 1. Therefore, the content of other monomers, including the acrylate esters (including lauryl acrylate), may be at least as low as 5% by weight, reading on the range stated in Claim 1. In addition, Hashimoto exemplifies as a second resin a styrene-acrylic resin having 10% by mass of lauryl acrylate (Page 22, Table 4, Example #20), reading on the range stated in Claim 1.
In preparing the toner of Matsushima as modified by Washino, and lacking guidance as to preferred contents of monomers in the vinyl resin, a practitioner of ordinary skill in the art would have looked to the prior art for a workable vinyl resin, which comprises long-chain (meth)acrylates and is incorporated as a minor component into a binder resin alongside a crystalline resin. The practitioner would thus be motivated to prepare a vinyl resin as taught by Hashimoto, which may be bonded to the amorphous polyester to form a hybrid amorphous resin. Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the instant application to prepare the toner of Matsushima having the shell taught by Washino, wherein the vinyl resin is bonded to the amorphous polyester resin, and comprises lauryl acrylate with a content, as taught by Hashimoto.
In the course of routine experimentation, one of ordinary skill in the art would arrive at a toner comprising a toner particle substantially similar to instant example 5 of the instant application (Specification, page 48, Table 3). This example possesses a value for loss elastic modulus G’’ of 4.0 x 107 Pa. Therefore, the toner of Matsushima having the shell taught by Washino and the hybrid amorphous polyester and vinyl resin composed as taught by Hashimoto would necessarily possess a roughly similar value for G’’, reading on the range stated in Claim 1.
Matsushima teaches that the vinyl resin should make up 0 – 50% by mass of the binder resin, depending on whether it is used in a color toner or a black toner ([0062]), encompassing the range stated in Claim 2.
Matsushima teaches that the toner contains a release agent ([0115]), and specifically points out behenyl behenate as an example ([0116]), reading on formula (4) of Claim 4.
As reported in the instant application, lauryl acrylate has a value for SP of 18.72 (J/cm3)1/2 (Specification, Table 1). This would be the value of SPm for the toner of Matsushima modified by the shell of Washino as described above, satisfying the range of SPm required by Claim 5. In addition, behenyl behenate has a value for SP of 17.56 (J/cm3)1/2 as reported in the instant application (Specification, Table 2). This would be the value of SPw for the toner of Matsushima modified by the shell of Washino as described above. Therefore, the difference between SPm and SPw for such a toner would be 1.16, satisfying formula (a) of Claim 5.
As discussed above, the amorphous polyester resin is preferably the main component of the binder resin, or at least 51% by mass. This would allow the amorphous polyester to comprise an amount of the fraction having a molecular weight of 2,000 or more lying in the range stated in Claim 11. Further, Matsushima teaches a preferred average circularity of the toner particles of 0.920 – 1.000, encompassing the range stated in Claim 11.
Claims 6, 7, and 10 are rejected under 35 U.S.C. 103 as being unpatentable over Matsushima et al (US PGP 2019/0094732) in view of Washino (US PGP 2019/0056678), further in view of Hashimoto et al (US PGP 2021/0181647), further in view of Kadonome et al (US PGP 2017/0307991).
The above discussions of Matsushima, Washino, and Hashimoto are incorporated herein. Matsushima teaches that an external additive to the toner may be organic particles, but does not appear to teach the type or preparation of such ([0149]).
Kadonome teaches a toner having an external additive (Abstract). Among the particles that may serve as an external additive, organic fine particles are mentioned. Kadonome teaches that these serve to improve charging performance, fluidity, or the cleaning properties of the toner ([0154]). Kadonome teaches that the organic fine particles may be composed of a styrene-acrylic resin ([0192]). One of the externally added organic fine particles exemplified by Kadonome is “large-diameter external additive E5” ([0302]), which is a “crosslinked vinyl-based resin” particle composed of monomers including methyl methacrylate, styrene, and divinylbenzene ([0303]), the same monomers which compose the particles of the instant application. Kadonome exemplifies a toner having these particles as an external additive ([0324] and page 22, Table 4, toner #12).
In preparing the toner of Matsushima modified with the shell of Washino and having the vinyl resin composed as taught by Hashimoto, a practitioner of ordinary skill would have been motivated to incorporate the externally added organic particles as taught by Kadonome, which impart improved charging performance, fluidity, and cleaning properties to the toner. Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the instant application to prepare the toner of Matsushima having the shell taught by Washino, and externally added with the organic particles of Kadonome, which are fine particles of crosslinked styrene-acrylic resin, resulting in a toner satisfying Claims 6 and 7.
Where Kadonome does not appear to teach preferred contents of specific monomer units in the crosslinked styrene-acrylic resin fine particles, it would have been obvious to one of ordinary skill in the art, through routine experimentation, to adjust the content ratios of various monomer units, arriving at a content of styrene in the particles lying in the range stated in Claim 10.
Claims 1, 2, and 11 are rejected under 35 U.S.C. 103 as being unpatentable over Sugawara et al (US Patent 10,732,532) in view of Washino (US PGP 2019/0056678).
Sugawara teaches a toner comprising toner base particles which include at least a binder resin. The binder resin includes a hybrid resin having a polyester segment and a styrene-acrylic segment (Abstract). Sugawara describes the components of the polyester segment of the hybrid resin (col. 6, line 21), and points out alkylene oxide adducts of BPA as preferable diol components of the polyester (col. 6, lines 30 – 44). Phthalic acid and its isomers are pointed out as preferable dicarboxylic acid components of the polyester (col. 7, lines 6 – 17). Thus, the polyester segment of the hybrid resin would have a cyclic structure in its main chain.
Sugawara describes the components of the styrene-acrylic (a type of vinyl resin) segment of the hybrid resin (col. 7, line 59), and states a preference for incorporation of (meth)acrylate ester monomers in the vinyl segment (col. 8, lines 30 – 37). Dodecyl (meth)acrylate is pointed out as a preferable monomer (col. 8, lines 47 – 51), reading on formula (1) of Claim 1. Sugawara teaches that the content of (meth)acrylic monomers to be polymerized in the styrene-acrylic resin is preferably 5 – 50% by mass (col. 8, lines 57 – 60), resulting in a monomer unit content overlapping the range stated in Claim 1. Further, Sugawara teaches that the content of styrene-based monomers (which may be styrene) to be polymerized in the styrene-acrylic resin is preferably 50 – 95% by mass (col. 8, lines 5 – 9), encompassing the range stated in Claim 1.
Sugawara teaches that another resin besides the hybrid resin may be included in the toner particle (col. 12, lines 22 – 24), and states a preference for a polyester resin (col. 12, lines 47 – 49). A crystalline polyester resin is described (col. 14, line 26), and monomer units including adipic acid, suberic acid, azelaic acid, sebacic acid, 1,9-nonanedicarboxylic acid, 1,10-decanedicarboxylic acid, 1,12-dodecanedicarboxylic acid, and 1,14-tetradecanedicarboxylic acid are pointed out as examples of dicarboxylic acid monomers which may be included in the crystalline polyester (col. 14, lines 35 – 40), which read on formula (B) of Claim 1. Ethylene glycol is pointed out as an example of a diol which may be used in the crystalline polyester resin (col. 14, lines 60 – 61), reading on formula (A) of Claim 1. Sugawara teaches that the content of the crystalline resin relative to the whole binder resin is preferably 2 – 40% by mass.
Sugawara teaches that the toner preferably has an average circularity of 0.91 – 0.98 (col. 18, lines 61 – 63), encompassing the range stated in Claim 1.
Sugawara teaches that the toner particles may have a core-shell structure, for the purpose of reducing gloss non-uniformity (col. 18, lines 22 – 34), but does not appear to teach a preferred material for the shell layer.
Washino teaches a toner having a core-shell structure ([0012]). Washino teaches that the shell layer preferably contains a thermosetting resin, from the viewpoint of making the shell sufficiently hard ([0035]).
In preparing the toner of Sugawara, a practitioner of ordinary skill in the art would have looked to the prior art for guidance as to an appropriate shell layer for the toner. The practitioner would therefore be motivated to incorporate the shell layer as taught by Washino, for the purpose of having a sufficiently hard shell layer. Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the instant application to prepare the toner of Sugawara having the shell layer taught by Washino. In the course of routine experimentation, one of ordinary skill in the art would arrive at a toner comprising a toner particle substantially similar to instant example 5 (Specification, page 48, Table 3). This example possesses a value for loss elastic modulus G’’ of 4.0 x 107 Pa. Therefore, the toner of Sugawara having the shell taught by Washino would necessarily possess a similar value for G’’ lying in the range stated in Claim 1.
Sugawara teaches that the styrene-acrylic copolymer portion of the hybrid resin should make up 10 – 60% by mass of the total of the hybrid resin (col. 9, lines 61 – 67). This would allow the amount of styrene-acrylic copolymer (analogous to vinyl resin) to represent an amount in the total of the binder resin having a molecular weight of 2,000 or more lying in the range stated in Claim 2.
Sugawara teaches that the polyester portion of the hybrid resin should make up 40 – 95% by mass of the total of the hybrid resin (col. 9, lines 54 – 60). This would allow the amount of amorphous polyester resin to represent an amount in the total of the binder resin having a molecular weight of 2,000 or more lying in the range stated in Claim 11. In addition, Sugawara teaches that the toner particles preferably have an average circularity of 0.91 – 0.98, encompassing the range stated in Claim 11.
Claims 4 and 5 are rejected under 35 U.S.C. 103 as being unpatentable over Sugawara et al (US Patent 10,732,532) in view of Washino (US PGP 2019/0056678), further in view of Matsushima et al (US PGP 2019/0094732).
The above discussions of Sugawara et al, Washino, and Matsushima et al are incorporated herein. While Sugawara teaches that a release agent may be an ester-based wax, such as a fatty acid ester (col. 15, line 64 – col. 16, line 3), neither of Sugawara or Washino appears to teach ester compounds according to instant formula (2), formula (3), or formula (4).
Matsushima teaches a wax which serves as a release agent ([0115]). Behenyl behenate is given as an example of an ester wax ([0116]), which reads on instant formula (4).
In preparing the toner of Sugawara having the shell layer taught by Washino, one of ordinary skill in the art would have been motivated to look to the prior art for a suitable ester wax-based release agent. Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the instant application to prepare the toner of Sugawara having the shell layer taught by Washino, and incorporating the ester wax (behenyl behenate) taught by Matsushima, resulting in a toner satisfying Claim 4.
As reported in the instant application, lauryl acrylate has a value for SP of 18.72 (J/cm3)1/2 (Specification, Table 1). This would be the value of SPm for the toner of Sugawara having the shell layer taught by Washino and the ester wax of Matsushima as described above, satisfying the range of SPm required by Claim 5. In addition, behenyl behenate has a value for SP of 17.56 (J/cm3)1/2 as reported in the instant application (Specification, Table 2). This would be the value of SPw for the toner of Sugawara having the shell layer taught by Washino and the ester wax of Matsushima as described above. Therefore, the difference between SPm and SPw for such a toner would be 1.16, satisfying formula (a) of Claim 5.
Claims 6, 7, and 10 are rejected under 35 U.S.C. 103 as being unpatentable over Sugawara et al (US Patent 10,732,532) in view of Washino (US PGP 2019/0056678), further in view of Kadonome et al (US PGP 2017/0307991).
The above discussions of Sugawara et al, Washino, and Kadonome et al are incorporated herein. Sugawara teaches that the toner may comprise an external additive (col. 19, lines 15 – 17), which may be resin particles (col. 19, lines 39 – 44). Neither of Sugawara or Washino appears to teach crosslinked resin fine particles as an external additive.
Kadonome teaches a toner having an external additive (Abstract). Among the particles that may serve as an external additive, organic fine particles are mentioned. Kadonome teaches that these serve to improve charging performance, fluidity, or the cleaning properties of the toner ([0154]). Kadonome teaches that the organic fine particles may be composed of a styrene-acrylic resin ([0192]). One of the externally added organic fine particles exemplified by Kadonome is “large-diameter external additive E5” ([0302]), which is a “crosslinked vinyl-based resin” particle composed of monomers including methyl methacrylate, styrene, and divinylbenzene ([0303]), the same monomers which compose the particles of the instant application. Kadonome exemplifies a toner having these particles as an external additive ([0324] and page 22, Table 4, toner #12).
In preparing the toner of Sugawara having the shell layer taught by Washino, a practitioner of ordinary skill would have been motivated to incorporate the externally added organic particles as taught by Kadonome, which impart improved charging performance, fluidity, and cleaning properties to the toner. Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the instant application to prepare the toner of Sugawara having the shell layer taught by Washino, and externally added with the organic particles of Kadonome, which are fine particles of crosslinked styrene-acrylic resin, resulting in a toner satisfying Claims 6 and 7.
Where Kadonome does not appear to teach preferred contents of specific monomer units in the crosslinked styrene-acrylic resin fine particles, it would have been obvious to one of ordinary skill in the art, through routine experimentation, to adjust the content ratios of various monomer units, arriving at a content of styrene in the particles lying in the range stated in Claim 10.
Conclusion
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 Grant S Seiler whose telephone number is (571)272-3015. The examiner can normally be reached 9:30 - 5:30 Pacific.
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/GRANT STEVEN SEILER/Examiner, Art Unit 1734
/PETER L VAJDA/Primary Examiner, Art Unit 1737
06/17/2026
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