Prosecution Insights
Last updated: October 27, 2026
Application No. 18/820,612

POLYIMIDE ADHESIVE COMPOSITION COMPRISING MALEIMIDE MOIETIES AND AMINE COMPOUND, ARTICLES AND METHODS

Final Rejection §103§112
Filed
Aug 30, 2024
Priority
Sep 16, 2022 — provisional 63/407,299 +1 more
Examiner
FREEMAN, JOHN D
Art Unit
1787
Tech Center
1700 — Chemical & Materials Engineering
Assignee
3M Innovative Properties Company
OA Round
2 (Final)
46%
Grant Probability
Moderate
3-4
OA Rounds
1y 8m
Est. Remaining
53%
With Interview

Examiner Intelligence

Grants 46% of resolved cases
46%
Career Allowance Rate
346 granted / 756 resolved
-19.2% vs TC avg
Moderate +7% lift
Without
With
+7.1%
Interview Lift
resolved cases with interview
Typical timeline
3y 10m
Avg Prosecution
24 currently pending
Career history
806
Total Applications
across all art units

Statute-Specific Performance

§101
0.3%
-39.7% vs TC avg
§103
45.4%
+5.4% vs TC avg
§102
16.2%
-23.8% vs TC avg
§112
33.3%
-6.7% vs TC avg
Black line = Tech Center average estimate • Based on career data from 756 resolved cases

Office Action

§103 §112
DETAILED ACTION Claim Rejections - 35 USC § 112 Claims 7, 8, and 17 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 applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention. Claim 7 recites “the adhesive layer comprises up to 5, [etc.] or 50 wt. % of moieties comprising an aliphatic moiety”. The claim is indefinite because it is not clear what is meant or encompassed by this phrase. A moiety refers to a part of a molecule. It is not clear how one would measure or calculate a weight percentage of moieties in an overall “adhesive layer”. Claim 8 recites “the adhesive layer comprises up to 5, 10, or 15 wt. % of polyether moieties”. The claim is indefinite because it is not clear what is meant or encompassed by this phrase. A moiety refers to a part of a molecule. It is not clear how one would measure or calculate a weight percentage of moieties in an overall “adhesive layer”. Claim 17 recites the limitation "the adhesive layer" in line 5 of the claim. There is insufficient antecedent basis for this limitation in the claim. Claim 17 recites “the adhesive layer comprises up to 5, 10, or 15 wt. % of polyether moieties”. As noted above, “the adhesive layer” lacks antecedent basis, which renders the claim indefinite; however, even if the claim were clarified that the “adhesive composition” comprises the claimed amount of “polyether moieties”, the claim would still be indefinite because it would not be clear what is meant or encompassed by the claim. A moiety refers to a part of a molecule. It is not clear how one would measure or calculate a weight percentage of moieties in an overall “adhesive composition”. Claim Rejections - 35 USC § 103 Claim(s) 1-3, 5-7, 10, 12-13, 15, 19, and 23 is/are rejected under 35 U.S.C. 103 as being unpatentable over Takeuchi et al. (US 2018/0009195) in view of Oka et al. (JP 2002-280688) or Motobe et al. (US 2006/0216495) as evidenced by the Technical Data Sheet for BMI-3000 (2020). Regarding claims 1-2 and 19: Takeuchi discloses a bonding sheet comprising a resin film of a resin composition for use in printed circuit boards (PCBs) [abstract; 0001; 0006-0008]. The sheet can be bonded to metal substrates and insulating layers [0112-0123]. The composition comprises a bismaleimide resin and a curing agent [0008; 0019]. The bismaleimide resin comprises a polyimide resin comprising maleimide moieties [0056-0058]. The resin is used in amount of 50% by mass or more [0024]. The curing agent comprises amines having two or more functional groups and is used in an amount of at least 2% by mass [0059-0062]. Example 1 discloses a resin composition comprising 80 g of bismaleimide resin (polyimide resin comprising maleimide moieties) commercially available as BMI-3000, 16g of a bismaleimide as a curing agent, 2 g of an aromatic diamine as a curing agent, and 2 g of peroxide, which is formed into a resin film [0138-0139]. The diamine is 2% by mass of solids of the composition. Takeuchi further discloses preparing a laminate comprising a LCP laminated product comprising a copper foil, the resin film, and a liquid crystal polymer film (insulating resin layer) [0142-0143]; and preparing a polyimide laminate comprising a copper foil, the resin film, and a polyimide film [0144-0145]. The present claims require two alternative requirements: a conductive metallic substrate having a particular surface roughness and/or an insulating resin layer comprising epoxy resin. With regard to the first alternative requirement, Takeuchi is silent with regard to the arithmetic surface roughness (Ra) of the copper layer. Surface roughness values of a copper layer within the claimed range were known in the art to have utility. For example, Oka discloses a copper foil having an adhesive for use in PCBs [abstract; 0001]. The copper has a surface roughness Ra of less than or equal to 0.5 µm to provide improved electrical properties [0004-0008]. Before the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to use Ra values of less than 0.5 µm to provide improved electrical properties as known in the art. With regard to the second alternative requirement, Takeuchi is silent with regard to an insulating layer comprising epoxy resin. This feature was known in the art to have utility. For example, Motobe discloses an epoxy resin composition for forming insulating layers in PCBs [abstract; 0001; 0095]. The composition comprises epoxy and silica filler [0009]. Before the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to use an insulating layer comprising epoxy to provide an insulating layer having desirable properties as known in the art. Regarding claim 3: Takeuchi discloses providing the conductor layer as a conductive pattern (trace) [0126-0130]. Regarding claim 5-6: Takeuchi discloses compounds within the scope of the present formula [0056-0058]. Additionally, the bismaleimide resin BMI-3000 has a structure within the scope of the present formula and comprises a pyromellitic dianhydride as the group Q as evidenced by the product’s datasheet. Regarding claim 7: See the rejection of the present claim under 35 USC 112. Takeuchi discloses a bonding sheet as previously explained. Additionally, the resin component has aliphatic hydrocarbon groups, which provides improved handling properties and strength [0040; 0049-0058]. Also see the formula disclosed in the datasheet for bismaleimide resin BMI-3000. Furthermore, the curing agent comprises aromatic amines or aliphatic amines [0061]. As noted above, the amount of resin is at least 50% by weight and the amount of curing agent is at least 2% by weight. Takeuchi is silent with regard to a weight percentage of moieties comprising an aliphatic moiety. Before the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to select from the disclosed resins and curing agents, including those having aliphatic components having a number of carbon atoms within the claimed range, and further vary the relative amount of the components over the disclosed ranges, including those that result in an amount of moieties within the claimed range, to provide a bonding sheet in accordance with Takeuchi’s teachings having the properties desired for a given end use. Regarding claim 10: Takeuchi teaches uniformly dispersing the components of the resin [0103]. Regarding claim 12: Takeuchi teaches thermal reaction initiators, e.g., peroxides, and inorganic fillers [0079-0083]. Regarding claim 13: As noted above, Takeuchi discloses the optional use of inorganic fillers, including silica and boron nitride [0082-0087]. Given that the use of such fillers is optional, the reference teaches amounts of 0% by weight of the fillers, which is an amount encompassed by the presently claimed range. Alternatively, Takeuchi teaches the amount of filler is 3-70% by volume [0085], but is silent with regard to a weight amount of inorganic filler. Before the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to vary the amount of filler, including over amounts falling within the claimed range, to provide the desired properties (e.g., curing, formability, etc.) for a given end use. Regarding claim 15: Takeuchi is silent with regard to an insulating layer comprising siliceous filler. Such features were known in the art to have utility. For example, Motobe discloses an epoxy resin composition for forming insulating layers in PCBs [abstract; 0001; 0095]. The composition comprises epoxy and silica filler [0009]. The silica is used in amounts of 3-80% by weight to provide improved viscosity properties which provides improved appearance in addition to improved thermal expansion, etc. [0006-0007; 0032-0039]. As set forth in MPEP 2144.05, in the case where the claimed range “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). Before the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to use an insulating layer comprising epoxy and silica, including wherein silica is used in amounts falling within the claimed range, to provide an insulating layer having desirable properties as known in the art. Regarding claim 23: Takeuchi discloses the use of aliphatic amines having at least two amine groups [0060-0061]. Although Takeuchi is silent with regard to a fatty diamine (i.e., dimer diamine) as the curing agent, the reference teaches such compounds were known in its discussion of the formation of the bismaleimide [0039]. Additionally, the structure of bismaleimide resin BMI-3000 indicates it is made from dimer diamine. Takeuchi teaches the resin component has aliphatic hydrocarbon groups, which provides improved handling properties and strength [0040; 0049-0058]. Therefore, before the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to use a dimer diamine (fatty diamine) as the aliphatic amine curing agent to provide the desired aliphatic groups, and thereby arrive at the claimed invention. Claim(s) 8-9 and 22 is/are rejected under 35 U.S.C. 103 as being unpatentable over Takeuchi et al. (US 2018/0009195) in view of Oka et al. (JP 2002-280688) or Motobe et al. (US 2006/0216495) as applied above, and further in view of Kuboki et al. (US 2021/0261736). Regarding claims 8-9: See the rejection of present claim 8 under 35 USC 112. Takeuchi discloses a bonding sheet as previously explained. The curing agent can be any compound having two or more functional groups that can react with the bismaleimide, and examples include aromatic, aliphatic, and alicyclic amines [0059-0061]. The amount thereof is at least 2% by mass of the composition [0062]. Takeuchi is silent with regard to a polyether component or a polyether amine. Such compounds were known in the art to have utility. For example, Kuboki discloses a maleimide resin composition useful for PCBs [abstract; 0001]. The composition comprises a bismaleimide resin and a curing agent [0014-0016; 0026-0028]. Kuboki teaches the curing agent comprises amino groups which can react with the maleimide groups, and includes conventionally known amine compound, such as polyoxypropylene diamine and polyoxypropylene triamine (i.e., polyether polyamines) [0071-0075]. Before the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to use polyether polyamines for the curing agent of Takeuchi because they were known to have utility as conventional curing agents as taught by Kuboki. Furthermore, before the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to vary the amount of such a curing agent, including over amounts that result in an amount of polyether moieties within the claimed range, to provide a bonding sheet in accordance with Takeuchi’s teachings having the properties desired for a given end use. Regarding claim 22: Takeuchi discloses the use of aliphatic amines having at least two amine groups [0060-0061]. Takeuchi is silent with regard to the number of carbon atoms in the amines. Compounds having a number of carbon atoms in the claimed range were known to have utility. For example, Kuboki discloses a composition as explained above. The reference discloses aliphatic amine compounds that are suitable as curing agents, including trimethylhexamethylenediamine, methylpentamethylenediamine, 1,3-bisaminomethylcyclohexane, etc. [0075]. Before the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to use any of the disclosed aliphatic amines for the curing agent of Takeuchi, including those having a number of carbon atoms falling within the claimed range, because they were known to have utility as conventional curing agents as taught by Kuboki. Claim(s) 11 is/are rejected under 35 U.S.C. 103 as being unpatentable over Takeuchi et al. (US 2018/0009195) in view of Oka et al. (JP 2002-280688) or Motobe et al. (US 2006/0216495) as applied above, and further in view of Abe et al. (US 2019/0281697). Regarding claim 11: Takeuchi discloses a bonding sheet as previously explained. The reference teaches silane coupling agents can be used with the metal foil to improve adhesion [0113]. Also see additional discussion of coupling agents with respect to the use of fillers [0086-0087]. Takeuchi is silent with regard to a concentration of an amine compound at the interface of the metal foil and the bonding sheet. Silane coupling agents having amino groups were known to have utility in the art. Abe discloses compositions comprising maleimide resin and a curing agent [abstract; 0001; 0013-0014]. The reference teaches the use of silane coupling agents, including amino-functional compounds, in amounts of 0.01-5 parts by mass or 0.1-20 parts by mass relative to 100 parts of resin to improve adhesion between adherends [0080-0083; 0121-0122]. Such compounds react with the substrate surface to create the “coupling” property. Before the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to use amino-functional silane coupling agents, including in amounts within the presently claimed range, to provide improved adhesion between the bonding sheet and the metal foil, and thereby provide a concentration of the amine compound at the interface of the two layers. Claim(s) 17 is/are rejected under 35 U.S.C. 103 as being unpatentable over Takeuchi et al. (US 2018/0009195) in view of Kuboki et al. (US 2021/0261736). Regarding claim 17: See the rejection of present claim 17 under 35 USC 112. Takeuchi discloses a bonding sheet comprising a resin film of a resin composition for use in printed circuit boards (PCBs) [abstract; 0001; 0006-0008]. The sheet can be bonded to metal substrates and insulating layers [0112-0123]. The composition comprises a bismaleimide resin and a curing agent [0008; 0019]. The bismaleimide resin comprises a polyimide resin comprising maleimide moieties [0056-0058]. The resin is used in amount of 50% by mass or more [0024]. The curing agent can be any compound having two or more functional groups that can react with the bismaleimide, and examples include aromatic, aliphatic, and alicyclic amines [0059-0061]. The amount thereof is at least 2% by mass of the composition [0062]. Takeuchi is silent with regard to a polyether component or a polyether amine. Such compounds were known in the art to have utility. For example, Kuboki discloses a maleimide resin composition useful for PCBs [abstract; 0001]. The composition comprises a bismaleimide resin and a curing agent [0014-0016; 0026-0028]. Kuboki teaches the curing agent comprises amino groups which can react with the maleimide groups, and includes conventionally known amine compound, such as polyoxypropylene diamine and polyoxypropylene triamine (i.e., polyether polyamines) [0071-0075]. Before the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to use polyether polyamines for the curing agent of Takeuchi because they were known to have utility as conventional curing agents as taught by Kuboki. Furthermore, before the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to vary the amount of such a curing agent, including over amounts that result in an amount of polyether moieties within the claimed range, to provide a bonding sheet in accordance with Takeuchi’s teachings having the properties desired for a given end use. Response to Arguments Applicant's arguments filed 7/28/2026 have been fully considered but they are not persuasive. Applicant states “As shown in the examples of the application under examination, the presence of the amine compound or reaction product thereof provides good adhesion to both, the metallic substrates (e.g. copper substrates) and the insulating resin layers (e.g. comprising epoxy resin)” (p7). Given that this is the only description provided, the examiner respectfully submits Applicant has failed to point out which data in particular is relied upon and has failed to explain the data provided as evidence of non-obviousness, which burden is placed upon Applicant. See MPEP 706.02(b). The examiner notes that Takeuchi already teaches the required use of an amine compound or reaction product thereof and so meets this required feature of the claimed invention. Applicant argues Takeuchi does not disclose metallic substrates having a surface roughness of less than 2 microns or an insulating resin layer comprising epoxy resin (p7). Applicant further argues Takeuchi discloses metallic substrates “must be roughened to achieve sufficient bonding” and therefore teaches away from the claimed surface roughness (p7). While the examiner agrees Takeuchi is silent with regard to a conductive metallic substrate having a particular surface roughness and an insulating resin layer, the examiner submits such features were recognized in the art as having utility as demonstrated by previously cited Oka and Motobe. Furthermore, the examiner notes independent claim 17 requires neither of these features noted by Applicant. With respect to Applicant’s argument that Takeuchi teaches away from the claimed surface roughness, the examiner first notes the claimed surface roughness is alternatively claimed. Regardless of Takeuchi’s implied surface roughness, the combination of Takeuchi in view of Motobe meets the alternatively claimed requirement of an insulating resin layer comprising epoxy resin, and so does not need to meet the claimed surface roughness. Additionally, however, the examiner does not agree with Applicant that Takeuchi teaches away from the claimed surface roughness. The reference at paragraph [0113] discloses “To increase the adhesion force with the resin film 11, the surface of the metal foil may be mechanically or chemically treated by chemical roughening; plating; and a treatment using aluminum alcoholate, aluminum chelate, a silane coupling agent or the like” [emphasis added by examiner]. The reference further discloses examples at paragraphs [0141], [0143], and [0145] discloses a “roughened surface of the copper foil” used therein. Nowhere does the reference require a particular surface roughness in terms of Ra of 2 or more microns. Furthermore, paragraph [0113] teaches any roughening is optional (“may be”), not a requirement. One of ordinary skill in the art would recognize the benefits of low surface roughness including values below 0.5 micron to provide improved electrical properties as taught by Oka. Therefore, the examiner maintains the claimed invention would have been obvious in view of Takeuchi and Oka. 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 JOHN D FREEMAN whose telephone number is (571)270-3469. The examiner can normally be reached Monday-Friday 11-8PM 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, Callie Shosho can be reached at 571-272-1123. 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. /JOHN D FREEMAN/Primary Examiner, Art Unit 1787
Read full office action

Prosecution Timeline

Aug 30, 2024
Application Filed
May 06, 2026
Non-Final Rejection mailed — §103, §112
Jul 28, 2026
Response Filed
Oct 13, 2026
Final Rejection mailed — §103, §112 (current)

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Prosecution Projections

3-4
Expected OA Rounds
46%
Grant Probability
53%
With Interview (+7.1%)
3y 10m (~1y 8m remaining)
Median Time to Grant
Moderate
PTA Risk
Based on 756 resolved cases by this examiner. Grant probability derived from career allowance rate.

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