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 and Claim 14 have been amended to narrow the scope of monomer (b) to a single alkyl chain length (variable “m” in formula (2) is 21). New dependent Claims 17, 18, and 19 have been added. No new subject matter has been added.
Response to Arguments
Applicant’s arguments, see remarks filed 2025-10-27 alongside amendments, with respect to the rejections of claims 1 - 16 under 35 U.S.C. §103 have been fully considered and are persuasive. Therefore, the rejection has been withdrawn. However, upon further consideration, new rejections are made over Nagaoka et al (US PGP 2020/0379363) in view of Nakajima (US PGP 2019/0317419) and Shimano et al (US PGP 2017/0052465) (see rejections below).
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 – 9, 11, and 15 - 19 are rejected under 35 U.S.C. 103 as being unpatentable over Nagaoka et al (US PGP 2020/0379363) in view of Hashimoto et al (US PGP 2019/0384193).
Nagaoka teaches a toner comprising a toner particle, which comprises a binder resin and inorganic fine particles (Abstract). The binder resin comprises a polymer A (analogous to resin A of the instant application), which includes a first monomer unit, and a second monomer unit, which is different than the first. The first monomer unit of polymer A is derived from a first polymerizable monomer, which is an alkyl (meth)acrylate having an alkyl group of 18 – 36 carbons ([0017]), such that the first monomer unit of polymer A reads on formula (1) of the instant application. Nagaoka’s polymer A is a crystalline resin ([0100]).
Nagaoka teaches that the content of the first monomer unit in polymer A is preferably 5 – 60% by moles ([0169]). Nagaoka does not appear to teach a preference regarding the content of the first monomer in polymer A on a parts-by-mass basis. However, Nagaoka’s example Toner 1 (page 23, Table 2) has a polymer A produced by incorporating 67% by mass of behenyl acrylate. Example toners 16 and 18 (page 24, Table 2 continued) possess behenyl acrylate contents by mass in polymer A of 30% and 80%, respectively. Example toners 1, 16, and 18 (page 24, Table 3) possess behenyl acrylate contents by mol % in polymer A of 28.88 mol %, 8.42 mol %, and 43.63 mol %, respectively, all of which lie inside Nagaoka’s preferred range (see above). Therefore, the content by mass parts of the first monomer unit (analogous to monomer unit (a) of the instant application) in Nagaoka’s polymer A (analogous to Resin A of the instant application) may have a value in a range which encompasses that claimed in the instant application.
Nagaoka teaches a preferred content of polymer A in the binder resin ([[0235]), but does not appear to teach a preferred content in the toner particle as a whole. However, Nagaoka does teach a preferred content of the inorganic fine particles contained in the toner particle of 20 – 150 parts by mass with respect to 100 parts of binder resin ([0121]). Toner example 35 has 50 parts of inorganic fine particles, 100 parts of polymerizable monomer mixture (page 24, Table 2-continued), as well as 10 parts of release agent and 0.7 parts of charge control agent ([0378] – [0385], [0393]). That example toner particle has a polymer A content of 62.2% by mass. Example 36 has only 30 parts of inorganic fine particles, giving a polymer A content of 71.1% by mass. Finally, a toner particle prepared in the same way and having Nagaoka’s minimum preferred content of inorganic fine particles of 20 parts would possess a polymer A content of 76.5% by mass. Therefore, the content of polymer A as a mass % may lie in a range (that is, below 60% to above 76%) significantly overlapping that stated in Claim 1.
Nagaoka teaches that the preferred melting point of polymer A is preferably 50 - 80°C ([0087]), overlapping the range stated in Claim 1. Nagaoka does not appear to teach an endothermic amount of the endothermic peak derived from polymer A, but since the amount of the first monomer present in polymer A taught by Nagaoka overlaps the amount specified in the pending claim, the resin of Nagaoka would necessarily satisfy the range for endothermic amount stated in Claim 1.
Nagaoka does not appear to teach a second binder resin in the toner particle reading on resin B.
Hashimoto teaches a toner comprising a binder resin which comprises a polymer A, having a first monomer unit and a second monomer unit (Abstract). The first monomer unit is a (meth)acrylate having an alkyl chain of 18 – 36 carbons ([0013]), and behenyl (meth)acrylate is pointed out ([0061], [0062]), reading on instant monomer unit (b) of resin B. Hashimoto does not appear to teach a preferred content of the first monomer unit in polymer A on a mass basis, but does teach a preferred content of 5 – 60% by moles ([0014]). Hashimoto discloses a preparative example in which polymer A contains behenyl acylate in an amount of 7% by moles, corresponding to 25% by mass (page 17, Table 2 continued, example 27). Where Hashimoto teaches that the content of the first monomer unit may be as low as 5% by moles, that would correspond to a content of roughly 18% by weight, overlapping the range stated in Claim 1.
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Hashimoto teaches that including the first monomer in polymer A in the stated amount imparts good low-temperature fixability and good charge rising properties ([0059]). Hashimoto also teaches that toners having crystalline vinyl resins as their binder resins possess slow charge rising ([0007]).
In preparing the toner of Nagaoka, one of ordinary skill in the art would have been motivated to improve the charge rising properties and low-temperature fixability of the toner by incorporating the polymer A taught by Hashimoto (analogous to instant resin B). 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 Nagaoka having a binder resin which also includes the polymer A of Hashimoto, resulting in a toner described by Claim 1.
Where the long-chain (meth)acrylates taught by both Nagaoka and Hashimoto may both be behenyl (meth)acrylate, the difference in the length of the alkyl groups may be 0, reading on Claim 2.
Nagaoka teaches a second monomer unit (analogous to monomer unit (c) of the instant application), different than the first monomer unit (analogous to monomer unit (a) of the instant application), is included in polymer A ([0179]). The second monomer unit may be derived from, for example, acrylonitrile or methacrylonitrile ([0180]). As seen on Table 5-2 of the instant application (Specification, page 63), the difference between the SP values of behenyl acrylate and methacrylonitrile is 7.7 units, lying in the range stated in Claim 4. Nagaoka gives a preference for the content of the second monomer unit in polymer A in terms of mol % ([0171]), but does not appear to teach a preference in terms of mass %. However, Table 2 of Nagaoka (pages 23 and 24) shows polymerizable monomer contents as weight parts of the binder resin. Nagaoka’s Toner 1 has 22 mass % of methacrylonitrile, Toner 17 has 26 mass % of acrylonitrile, Toner 21 has 32 mass % of acrylonitrile, Toners 15 and 16 have 35 mass % of acrylonitrile, and Toner 23 has 80 mass % of acrylonitrile. These values overlap the range stated in Claim 4.
As mentioned in the discussion of Claim 4 above, Nagaoka’s second monomer unit (analogous to monomer unit (c) of the instant application) may be acrylonitrile or methacrylonitrile, satisfying Claim 5.
Hashimoto teaches that the weight-average molecular weight of the THF soluble portion of polymer A (analogous to instant resin B) as measured by GPC is preferably in the range of 10,000 – 200,000, reading on the range stated in Claim 6, Claim 15, and Claim 16.
Hashimoto teaches that the acid value of polymer A (analogous to instant resin B) is preferably 0 – 30 mg KOH/g, reading on the range stated in Claim 7. Nagaoka discloses the preparation of polymer A0, which contains behenyl acrylate, methacrylonitrile, and styrene ([0346] – [0347]). The reported acid value for this polymer is 0.0 mg KOH/g ([0348]). Therefore, acid value of Hashimoto’s polymer A may be greater than that of Nagaoka’s polymer A by a margin of more than 5 mg KOH/g, satisfying the inequality stated in Claim 7.
As mentioned in the discussion of Claim 7 above, Nagaoka’s polymer A0 (analogous to resin A of the instant application) has an acid value of 0.0 mg KOH/g, satisfying Claim 8.
Nagaoka teaches preferred SP values for monomer units included in polymer A, but does not appear to teach a preference for or report SP values for polymer A. Hashimoto teaches preferred SP values for first and second monomers, but not for the polymer A. However, Nagaoka’s polymer A, being able to conform to the composition required of instant resin A, and Hashimoto’s styrene-acrylic resin, able to conform to the composition required of instant resin B, would together inherently possess SP values such that the difference between the two satisfies the inequality stated in Claim 9.
As discussed above, the first monomer unit (which may be behenyl acrylate) of Hashimoto’s polymer A (analogous to instant resin B) may be included in an amount as low as ~18% by mass, reading on the range stated in Claim 11.
As discussed above, Hashimoto’s first polymerizable monomer contained in polymer A may be behenyl acrylate. In addition, Hashimoto teaches that two or more kinds of second polymerizable monomer may be used in combination to prepare polymer A ([0082]). Specifically pointed out are acrylonitrile ([0083]) and methacrylic acid ([0089]). Hashimoto teaches that a third polymerizable monomer is also preferably used ([0120]), which may be styrene ([0123]). Therefore, Hashimoto’s polymer A (analogous to instant resin B) may read on the copolymer described by Claim 17.
As discussed above, Nagaoka’s first polymerizable monomer contained in polymer A may be behenyl acrylate. In addition, Nagaoka teaches that two or more second polymerizable monomers may be used in combination to prepare polymer A ([0179]). Specifically pointed out is methacrylonitrile ([0180]). In addition, the second polymerizable monomer also preferably contains a unit described by formula (E) ([0190]). Where R8 of formula (E) may represent a group of -CO2CH2CH3 ([0192] – [0195]) and where R10 may represent a methyl group ([0199]), ethyl methacrylate would conform to formula (E). Nagaoka teaches that polymer A may further contain a third monomer unit ([0215]), which may be styrene ([0221] – [0222]). Therefore, Nagaoka’s polymer A (analogous to instant resin A) may read on the copolymer described by Claim 18.
The monomers mentioned in the discussion above of Claims 17 and 18 allow the polymers of Nagaoka and Hashimoto to read on the copolymers described by Claim 19.
Claims 1, 3, 10, 12, and 13 are rejected under 35 U.S.C. 103 as being unpatentable over Nagaoka et al (US PGP 2020/0379363) in view of Nakajima (US PGP 2019/0317419).
The above discussion of Nagaoka is incorporated herein.
Nakajima teaches a toner comprising a binder resin ([0098]), which contains an amorphous resin and a crystalline resin ([0099]). The amorphous resin is preferably an amorphous vinyl polymer ([0100]). The amorphous vinyl polymer is preferably a styrene-acrylic resin, and behenyl acrylate is pointed out as a preferable monomer included in the resin ([0107]), reading on instant monomer unit (b) of resin B. Nakajima teaches that incorporation of such a monomer unit into the amorphous vinyl resin contributes to improved low-temperature fixability and thermal resistivity of the toner ([0108]). Nakajima also teaches that inclusion of the amorphous vinyl resin alongside a crystalline binder resin improves document offset properties ([0111]). Nakajima does not appear to teach preferred contents of various monomer units in the amorphous vinyl resin.
In preparing the toner of Nagaoka, one of ordinary skill in the art would have been motivated to include the amorphous vinyl resin of Nakajima into the binder resin of the toner in order to improve the low-temperature fixability, thermal resistivity, and document offset properties of the toner. Where Nagaoka teaches that higher content of a monomer unit having a long-chain alkyl group (such as behenyl acrylate) contributes to increased crystallinity of a polymer ([0053]), one of ordinary skill in the art would have understood that the content of long-chain (meth)acrylates (such as behenyl acrylate) in the amorphous vinyl resin would need to be less than 50% by mass. 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 Nagaoka, incorporating the amorphous vinyl resin of Nakajima having a content of behenyl acrylate reading on the range stated in Claim 1.
Nakajima teaches that document offset properties are improved by the inclusion of the amorphous vinyl resin in the toner particles in an amount of 10 – 90% by mass, overlapping the range stated in Claim 3.
Nakajima describes a hybrid resin comprising a segment of amorphous styrene-acrylic resin ([0129]), and that this is preferably the same kind of resin as the previously described amorphous resin used in the binder resin ([0160]). Nakajima teaches that the glass transition temperature of such a segment is preferably 30 - 80°C ([0158]). The amorphous vinyl resin previously described, being the same kind of resin, would thus possess a glass transition temperature in the same range, reading on the range recited in Claim 10.
In addition, Nakajima teaches monomer units other than behenyl acrylate which may be incorporated in the amorphous vinyl resin, in combination of two or more ([0102]), including styrene ([0102]-(1)), methacrylonitrile, and methacrylic acid ([0102]-(7)). Selecting among these monomer units, being the same as those used in almost all examples of instant resin B, the amorphous vinyl resin of Nakajima would inherently possess a similar glass transition temperature to those resins. The instant examples of resin B all possess values for the glass transition temperature lying in the range stated in Claim 10 (Specification, Table 1), and so the amorphous vinyl resin of Nakajima would also necessarily possess a value for the glass transition temperature lying in the range stated in Claim 10.
Where, as described above, Nagaoka’s polymer A (analogous to instant resin A) may have a content in the binder resin of greater than 76% by mass, and, as described above, the amorphous vinyl resin of Nakajima (analogous to instant resin B) may be included in the toner in an amount as high as 90% by mass, the two resins together would be able to make up a portion by mass of the binder resin of at least 80%, satisfying Claim 12.
As mentioned above, Nagaoka’s polymer A (analogous to instant resin A) is a crystalline vinyl resin, and Nakajima’s amorphous vinyl resin (analogous to instant resin B) is an amorphous resin, satisfying Claim 13.
Claim 14 is rejected under 35 U.S.C. 103 as being unpatentable over Nagaoka et al (US PGP 2020/0379363) in view of Nakajima (US PGP 2019/0317419), further in view of Shimano et al (US PGP 2017/0052465).
The above discussions of Nagaoka and Nakajima are incorporated herein.
Nagaoka teaches the suspension polymerization method of toner production ([0272]), but does not appear to teach a method of including another resin in the monomer mixture for the main component of the binder resin.
Shimano teaches a toner comprising a toner particle having a core-shell structure, wherein the core contains an amorphous resin A and a crystalline resin (Abstract). Shimano teaches that the crystalline resin is considered the binder resin of the toner particle ([0030], [0039]). Shimano teaches that suspension polymerization is the preferred method of producing the toner ([0063]). In this method, a monomer composition is prepared, which includes at least the crystalline resin (a minor component of the core) and the polymerizable monomers which will form the amorphous resin A (main component of the binder resin and core) ([0064]). The monomer mixture is then suspended in an aqueous medium ([0065] – [0066]), and the monomers are polymerized to yield toner particles ([0067]). Shimano discloses a preparative example in which the crystalline resin is included in the vinyl monomer composition which is used to polymerize amorphous resin A ([0143] – [0144]).
In preparing the toner taught by Nagaoka as modified with the amorphous vinyl resin of Nakajima, one of ordinary skill in the art would have looked to the prior art for guidance as to an appropriate method of achieving suspension polymerization of the main component of the binder resin of the toner particle, wherein the binder resin also contains another resin as a minor component. Motivated by Shimano’s method, which includes the minor component resin, already polymerized, into the monomer composition for the suspension polymerization of the main component, it would have been obvious to one of ordinary skill in the art before the effective filing date of the instant application to include the styrene-acrylic resin of Nakajima (minor component) in the monomer composition for the polymer A of Nagaoka (main component), and to then polymerize the monomer composition to yield a toner particle. These steps read on the method disclosed in Claim 14.
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 12/2/2025