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 .
Applicant’s preliminary amendment dated 2 June 2023 is acknowledged. Claims 1-20 as amended are pending.
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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.
Claim(s) 1, 3, 4, 9, 12, 13, and 15-17 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Liu et al., “Bismaleimide-diamine copolymers containing phthalide cardo structure and their modified BMI resins,” High Performance Polymers 30(5), 527-538 (2018) (“Liu”).
As to claim 1, Liu teaches a resin having the structure
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(p. 529, 2nd col.). This resin is a bismaleimide compound meeting Formula (1) where T is a divalent binding unit containing a cardo moiety, Ra and Rb are each a binding unit containing an aromatic moiety, R1 and R2 are hydrogen, and n is 1.
As to claim 3, the resin of Liu meets formula 1. X, a moiety of formula 2, is optional under claim 1.
As to claim 4, the resin of Liu has Ra and Rb being an aromatic moiety having 13 carbon atoms.
As to claim 9, the resin of Liu has Ra and Rb being an aromatic moiety having 13 carbon atoms. Rc is optional under claim 1.
As to claim 12, Liu teaches curing the resin (p. 528, 2nd col. – 529, 1st col.).
As to claim 13, Liu teaches curing with other monomers (Liu, p. 529, 1st col.).
As to claim 15, Liu teaches curing to a polymer (p. 529, 1st col.).
As to claim 16, Liu teaches curing to a polymer (p. 529, 1st col.). Having the same structure, it is presumed to be dielectric.
As to claim 17, Liu teaches curing to a polymer (p. 529, 1st col.). Having the same structure, it is presumed to be dielectric. The double bonds of the maleimide units are presumed to be the reactive groups (see Liu, p. 531, 1st col., discussing maleimide double bonds required for curing), and therefore it is reasonable to expect that the resulting polymer retains the structure of formula (12).
Claim(s) 1, 3-5, 8, 9, 12, 15-17, and 20 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Xiong et al., “New chain-extended bismaleimides with aryl-ether-imide and phthalide cardo skeleton (I): Synthesis, characterization and properties,” Reactive and Functional Polymers 129, 29-37 (2018) (“Xiong”).
As to claim 1, Xiong teaches a bismaleimide compound having the general structure
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and specifically a species where n = 2. (Xiong, p. 31, MPEIBMI-1.5). For n is 2, the structure meets Formula (1) of claim 1 where n = 1 as recited, T is a divalent unit comprising a cardo moiety, Ra and Rb are each a cardo moiety, R1 and R2 are hydrogen.
As to claim 3, as discussed with respect to claim 1, Xiong teaches a structure of Formula (1). X is a moiety of Formula (2) and therefore optional under claim 1.
As to claim 4, the compound of the above formula with n = 2 corresponds to a compound of Formula (1) where Ra and Rb are each a cardo moiety having 34 carbon atoms.
As to claim 5, the compound of the above formula with n = 2 corresponds to a compound of Formula (4) where T1 is a substituted cardo moiety having 80 carbon atoms and n = 1, and Ra and Rb are each a substituted cardo moiety having 34 carbon atoms.
As to claims 8 and 20, as discussed with respect to claim 5, Xiong teaches a structure of Formula (4). X1 is a moiety of Formula (5) and therefore optional under claim 5.
As to claim 9, the compound of the above formula with n = 2 corresponds to a compound of Formula (1) where Ra and Rb are each a cardo moiety having 34 carbon atoms. Rc is a moiety of formula (2) and therefore optional under claim 1.
As to claims 12, 15, and 16, Xiong teaches curing a formulation of the bismaleimide compound (p. 33, section 2.3). It is presumed the result is a dielectric polymer material.
As to claim 17, Xiong teaches curing a formulation of the bismaleimide compound (p. 33, section 2.3). It is presumed the result is a dielectric polymer material. Since the starting material had the repeating unit of formula (12), the resulting polymeric material is presumed to have that structure.
Claim(s) 1-4, 9-12, and 15-17 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by JP H03-192121 A (“Suga”).
A partial machine translation is enclosed.
As to claim 1, Suga teaches a prepolymer that is obtained from the reaction of an excess of a bismaleimide and a diamine compound. Specifically, example 4 (translation, p. 9) teaches a reaction of 313.9 g of 9,9-bis-(N-4-maleimidophenyl)fluorene with 86.1 g of α,α-bis-(4-aminophenyl)fluorene. The molar ratio is 2.5 parts of the bismaleimide to 1 part of the diamine compound. While not explicitly stated, the addition of these two compounds would be expected to result in a prepolymer having excess maleimide groups, at least some portion, given the stoichiometric ratio, of Formula (1), where n = 1, T is a group derived from the fluorene diamine, therefore having a cardo moiety, Ra and Rb each being a divalent binding unit having a fluorene, thus cardo, moiety, and R1 and R2 being hydrogen.
As to claim 2, the moiety T would be expected to come from α,α-bis-(4-aminophenyl)fluorene, and therefore meet structure of Formula (3b).
As to claim 3, the prepolymer of example 4 is expected to meet formula (1). X is optional under claim 1.
As to claim 4, the Ra and Rb moiety are derived from 9,9-bis-(N-4-maleimidophenyl)fluorene, and therefore are a cardo moiety having 24 carbon atoms.
As to claim 9, the Ra and Rb moiety are derived from 9,9-bis-(N-4-maleimidophenyl)fluorene, and therefore are a cardo moiety having 24 carbon atoms. Rc is optional under claim 1.
As to claims 10 and 11, the Ra and Rb moiety are derived from 9,9-bis-(N-4-maleimidophenyl)fluorene, and therefore meet Formula (9) were p is 0, GR is a single bond, and R is Formula (10d) of claim 10 and Formula (11c) of claim 11.
As to claim 12, Suga teaches curing the prepolymer (translation, p. 8).
As to claims 15 and 16, Suga teaches a cured product ( translation, p. 8). It is presumed to have dielectric properties, being the same material as recited. Given that the prepolymer is maleimide functional, it is reasonable to presume the product is polymeric.
As to claim 17, Suga teaches a cured product (translation, p. 8). It is presumed to have dielectric properties, being the same material as recited. Given that the prepolymer is maleimide functional, it is reasonable to presume the product is polymeric. It is reasonable to presume that the product would have the same prepolymer linkage of Formula (12).
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, 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 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.
Claim(s) 14 and 18 are rejected under 35 U.S.C. 103 as being unpatentable over JP H03-192121 A (“Suga”).
As to claim 14, the discussion of Suga with respect to claim 12 is incorporated by reference. While not exemplified, Suga teaches that the prepolymer may include fillers when curing (translation, p. 7), and as such, inorganic filler is an obvious additive suggested by Suga.
As to claim 18, the discussion of Suga with respect to claim 15 is incorporated by reference. While not exemplified, Suga teaches that the prepolymer has good electrical properties, and may be used as IC sealant, which is an electronic device (translation, p. 4). As such, the use of the resin for such purpose is an obvious modification suggested by Suga.
Claim(s) 19 is rejected under 35 U.S.C. 103 as being unpatentable over JP H03-192121 A (“Suga”) as applied to claim 18, further in view of US 2020/0185346 (“Venkatadri”).
As to claim 19, Suga teaches a cured product of dielectric properties, but does not teach the recited type of device. However, it is known that insulating repassivation layers are required on redistribution layers in chip packages (Venkatadri, para. 0017). Given that Suga teaches dielectric (insulating) material suitable for electronic purposes, the use of such material as a repassivation layer is an obvious end use as taught by Venkatadri.
Claim(s) 1-9, 12, 13, 15-18, and 20 are rejected under 35 U.S.C. 103 as being unpatentable over US 2020/0041903 (“Takemura”).
As to claims 1 and 9, Takemura teaches a polyimide compound that is formed by one of a diamine of the following diamines
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and one of the following dicarboxylic anhydrides
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(abstract) where Z is a cyclic structure bound to one C atom, and thus a cardo structure. The resulting polyimide resin has one of the following structures
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(para. 0153). This structure meets Formula 1 where Ra is a divalent binding unit that is aromatic, and T is a divalent unit having a cardo moiety.
Takemura does not explicitly teach a range for n in Formula (1). Takemura teaches that the preferred molecular weight is 7000 to 30000 (para. 0174). For example, using the recited diamines in combination with the dianhydride
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(para. 0264), would provide a resin having approximately 9 to 40 units. Given the monomers taught by Takemura and preferred molecular weight, the recited polymer length is an obvious modification.
Takemura does not exemplify the end units; however, Takemura teaches the utility of endcapping the resin with either monoamines or monoanhydrides, the monoanhydride, the monoanhydride may be maleic anhydride (paras. 0175-0178). Blocking the ends of an amine terminated polymer unit with maleic anhydride would provide the recited structure having the recited Ra and Rb units as required by claims 1 and 9 (substituted aromatic moiety of the recited carbon atoms), with R1 and R2 being hydrogen. As such, blocking the ends of the resin with maleic anhydride, thus forming a bismaleimide, is an obvious modification shown to be useful in controlling molecular weight.
As to claim 2, as one example, Takemura teaches the use of the dianhydride
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(para. 0264), which meets the formula 3b.
As to claim 3, as discussed with respect to claim 1, Takemura discloses a structure of Formula (1). X is optional under claim 1.
As to claim 4, referring to the structures discussed above with respect to claim 1, Takemura as modified suggests Ra and Rb being a substituted aromatic moiety in the recited range.
As to claim 5, the resin structures of formula 7 and 8 discussed with respect to claim 1, when capped with maleic anhydride, provide a bismaleimide resin of formula (4) where T1 is a cardo moiety, and Ra is a substituted aromatic moiety of the recited number of carbon atoms.
As to claim 6, the resin structure of formula 7 and 8 discussed with respect to claim 1 meet T1 where each GT is a single bond and T is formula 3a. Other formula of para. 0264 exemplify different claimed structures.
As to claims 7, 8, and 20, as discussed above, Takemura as modified suggests Formula (4) of claim 5. X1 is optional under claim 5.
As to claims 12, 15, and 16, Takemura teaches forming a resin composition of the polymer (para. 0187) and curing (para. 0228). Being the same material, it is presumed to form a dielectric polymeric material.
As to claim 13, Takemura teaches crosslinking agents (para. 0189), which are presumed to react with the resin (via the hydroxyl groups) (para. 0189).
As to claim 17, Takemura teaches forming a resin composition of the polymer (para. 0187) and curing (para. 0228). Being the same material, it is presumed to form a dielectric polymeric material, and presumed to have structures of Formula (12).
As to claim 18, Takemura teaches the use of this composition for electronic devices (para. 0002).
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-20 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-3, 5, 7-9, 11, and 13-20 of copending Application No. 18/280,081 (reference application).
Copending claim 1 recites Formula (1) which meets the structure of recited Formula (1) when A contains a cardo center, and therefore claim 1 is an obvious modification of copending claim 1. Formula (2) of copending claim 1 meets Formula (1) of claim 1 when A is a cardo moiety. Copending claim 2 teaches B and Z moieties, corresponding to X of recited Formula (2) as required by claim 3. Copending claim 3 meets the recitation of Ra and Rb of claim 4. Copending claim 5 teaches Formula 3a and 4a which meet recited formula (4) and (5) of claim 5 when A1 is a cardo/spiro moiety.
Copending claims 7 and 8 teaches moieties for B1 and Z1 which meet recitation for X1 in claims 7, 8, and 20. The structures of claim 8 also meet the formulae of claim 2. Copending claim 9 recites structures of claim 9. Copending claim 11 recites structures meeting Formula 9 of claims 10 and 11. Copending claims 13-20 recite the additional limitations required by claims 12-19, respectively. Given that the copending claims teach a structure meeting recited structures including a cardo spiro moiety, modifying the claims to use a cardo/spiro group is an obvious modification.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Conclusion
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/KREGG T BROOKS/Primary Examiner, Art Unit 1764