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
Applicant’s claim amendments and remarks filed October 8, 2025 are entered and have
been fully considered. Applicant has amended the claims to overcome the objections and 112b rejection, therefore the 112b rejections and objections are withdrawn. Claims 1-8 and 13-20 have been cancelled. Applicant has amended the claims to overcome the double patenting rejections, therefore they are withdrawn.
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.
Claims 9-12, 21-24, and 29-35 are rejected under 35 U.S.C. 103 as being unpatentable over Takezawa et al, US20180163015A1 in view of the ACS article, “Highly Oriented Liquid Crystalline Epoxy Film: Robust High Thermal Conductive Ability,” by Tanaka et al further in view of Roh et al, WO2019146990 (use US20210091293 for translation and paragraph numbers).
Regarding claims 9-10, Takezawa teaches a composition comprising a liquid crystalline epoxy compound which comprises a monomer that contains the structure of applicant’s M-1 of instant claim 21 ¶[0020], and a curing agent (abstract). It is further taught the epoxy resin further comprises filler particles of the size 0.1µm-100µm ¶[0068]. Takezawa also teaches coating a metal substrate with at least one cured layer of the resin composition, ¶[0202], which reads on the claimed primer layer.
Takezawa does not teach applying the LC epoxy composition to a substrate with a surface free energy (SFE) of 50 mN/m or higher and with a surface roughness (Ra) of the substrate facing the primer layer is 1-25 µm.
Tanaka discloses a composition comprising a liquid crystalline monomer with a structure that corresponds to applicant’s (M-2) of instant claim 21, and a curing agent, see abstract and section 2.3, Fig. 1. It is disclosed that a smectic phase with homeotropic alignment is formed on the glass substrates that have surface free energies of 71.3 mN/m and 72.7 mN/m, but only forming a planar alignment on substrates with SFE 46.3 mN/m, (abstract). These surface energies of the substrates are accomplished by surface treatment, section 2.2. This homeotropic alignment resulted in remarkable thermal conductivity measurements compared to thermosetting polymers and ceramic glass, which allows the LC epoxy resin to be applied to high-thermal conductive adhesives (which is a type of primer) and packaging materials in electrical and electronic devices, (abstract).
Roh discloses a thermoelectric element comprising a metal substrate and a resin layer on the metal substrate, abstract. The thermoelectric elements are used in electronic components ¶[0005]. The resin layer can be a mesogenic crystalline epoxy with a curing agent, ¶[0081]. The epoxy resin further contains a first inorganic filler ¶[0010]. The metal substrate has a first region and a second region, where the second region has a higher surface roughness than the first, and the epoxy resin layer is disposed onto the second region, ¶[0009]. Roh further discloses that the surface roughness (Ra) of the second region is 1.05-1.5 times greater than the particle size of the first inorganic filler ¶[0011-0012]. This causes the epoxy resin and filler to be disposed in the grooves formed due to surface roughness, ¶[0016], and the adhesion between the resin layer and the metallic substrate is increased ¶[0092].
Applying the recommended surface roughness to the composition of Takezawa, the boron nitride particles of Takezawa are 0.1-100µm as stated above, therefore the surface roughness of the metal substrate can be (0.1x1.05)= 0.105 µm minimum to (100x1.5)= 150 µm maximum, which encompasses the claimed range. Takezawa states that the preferable particle size is 0.1-20 µm ¶[0068], which means the preferable surface roughness is 0.105 µm to (20x1.5)= 30 µm, which also encompasses the claimed range.
Takezawa and Tanaka are analogous to the claimed invention because both are in the field of liquid crystalline epoxy resin compositions.
Roh is analogous to the claimed invention because it is in the field of substrates bonded to epoxy resins for use for electronic devices/components.
It would have been obvious to a person having ordinary skill in the art at the time the invention was filed to practice the invention of Takezawa but surface treating the metal substrate to have a surface free energy of 71.3 or 72.7 mN/m because Tanaka teaches that surfaces treated to have the above surface energies produce homeotropic alignment of the LC epoxy monomers and remarkable thermal conductivity is produced, and further forming a surface roughness (Ra) on the metal substrate of 0.105 µm-150 µm (preferably 0.105 µm- 30 µm) because the epoxy resin and filler will be disposed in the grooves and increase the adhesion between the resin and substrate as disclosed by Roh.
Regarding claims 11 and 12, the difference between claims 9-10 and 11-12 is the addition of the insulating member over the primer layer.
Takezawa teaches that the composition is used as a heat dissipation material for heat-generating electronic components such as integrated circuit (IC) chips or printed circuit boards, ¶[0157], which are types of semiconductor devices. Takezawa teaches a printed circuit board comprising a wiring layer, a metal plate, and at least one cured layer formed from the LC epoxy composition in the form of a resin layer, a B-stage sheet (semi-cured) or a prepreg disposed between the metal substrate and the wiring layer, ¶[0213]. The LC epoxy resin has boron nitride particles which have an insulating property ¶¶[0003, 0008].
The cured layers, such as the B-stage sheet, of the LC epoxy resin disposed between the metal plate and the circuit board act as an electrical insulator, ¶[0172]. Because multiple layers of the different forms of the LC epoxy resin can be used, the initial layer acts as a primer for the next layer which is the insulating member for the semi-conductor device.
Regarding claims 21-24, 29-35, Takezawa teaches a composition comprising a liquid crystalline epoxy compound and a curing agent (abstract). The liquid crystalline (LC) epoxy comprises a monomer represented by formula (I), below, ¶[0020], which includes the structure of applicant’s (M-1).
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Also, in example 1, ¶[0221], the LC epoxy monomer (4-{4-(2,3-epoxypropoxy)phenyl}cyclohexyl-4-(2,3-epoxypropoxy)benzoate is exemplified, which is exemplified by applicant in ¶[0039] of the instant specification as a preferred example including the structure M-1. In example 6, ¶[0252], the LC monomer (1-(3-methyl-4-oxiranylmethoxyphenyl)-4-(oxiranylmethoxyphenyl)-1-cyclohexane) is exemplified, which is exemplified by applicant in ¶[0039] of the instant specification as a preferred example including structure M-2.
Takezawa further teaches that the curing agent is an amine or phenol curing agent ¶[0137], with a phenol curing agent and triphenylphosphine accelerator being exemplified in the examples, ¶[0221]. The LC epoxy resin forms a smectic domain (periodic structure) after reacting with the curing agent, ¶[0058], and also see Table 2 on page 16, where the examples 1-7 all have the presence of the smectic domain (periodic structure), with a 2.5 nm cycle length. An alcohol solvent such as isobutyl alcohol may be added to the LC epoxy composition, ¶¶[0145-0146]. And the LC epoxy resin is applied to a metal substrate, ¶¶0001, 0038-0041].
Claims 25-28, are rejected under 35 U.S.C. 103 as being unpatentable over Takezawa et al, US20180163015A1 in view of the ACS article, “Highly Oriented Liquid Crystalline Epoxy Film: Robust High Thermal Conductive Ability,” by Tanaka et al further in view of Roh et al, WO2019146990 (use US20210091293 for translation and paragraph numbers) further in view of Takezawa et al, WO2017122350 (referenced as Takezawa-2).
Regarding claims 25-26, Takezawa modified by Tanaka and Roh teach the invention according to claims 9 and 21, as explained above. Modified Takezawa teaches the general prepolymer process of reacting LC epoxy monomer with curing agent to create an LC epoxy prepolymer of Claim 3 ¶[0121] but does not exemplify this process and does not list the specific curing agent phenol compounds recited by Claim 3. Modified Takezawa exemplifies a phenol curing agent (See Example 1) but does not teach any of the phenol compounds of Claim 3. The examples utilize triphenylphosphine as a curing accelerator to finish curing the resin ¶[0221].
Takezawa-2 discloses an epoxy resin composition comprising a liquid crystalline epoxy monomer and a curing agent ¶[0050]. The composition also has high thermal conductivity and a highly ordered structure, ¶[0051], similar to modified Takezawa. Takezawa-2 in ¶[0062] teaches the same prepolymer process as modified Takezawa. Takezawa-2 lists specific phenol curing agents such as hydroquinone ¶[0073]. When a phenolic curing agent is used, an accelerator is also used to sufficiently cure the resin ¶[0075]. Takezawa-2 further discloses the curing accelerator as triphenylphosphine in example 1 ¶[0140].
Takezawa and Takezawa-2 are analogous to the claimed invention because both are in the field of liquid crystalline epoxy compositions.
Therefore it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to practice the invention of modified Takezawa (2018) by using a prepolymer of the LC epoxy monomer which is reacted with the curing agent to be partially polymerized because modified Takezawa (2018) teaches this in ¶[0121] and choose the curing agent for this prepolymer to be hydroquinone because Takezawa-2 teaches such a phenol curing agent compound for use in the same prepolymer process as Takezawa. One of ordinary skill in the art would have been motivated to choose phenol curing agents such as hydroquinone because Takezawa exemplifies that category of curing agent.
Regarding claims 27-28, Modified Takezawa further teaches the LC epoxy resin forms a smectic domain (periodic structure) after reacting with the curing agents, ¶[0058], and also see Table 2 on page 16, where the examples 1-7 all have the presence of the smectic domain (periodic structure), with a 2.5 nm cycle length. An alcohol solvent such as isobutyl alcohol may be added to the LC epoxy composition, ¶¶[0145-0146].
Claims 9-12, 21-22, 24-26, 28-29, 31, 34-35 are rejected under 35 U.S.C. 103 as being unpatentable over Takezawa et al, WO2017122350A1 in view of the ACS article, “Highly Oriented Liquid Crystalline Epoxy Film: Robust High Thermal Conductive Ability,” by Tanaka et al further in view of Roh et al, WO2019146990 (use US20210091293 for translation and paragraph numbers).
Regarding claims 9-10, Takezawa teaches a composition comprising a liquid crystalline epoxy compound and a curing agent ¶[0006] (see ¶[0007] of original document for structure). It is taught the epoxy resin further comprises filler particles of the size 0.1µm-100µm ¶[0037]. Takezawa also teaches coating a metal substrate with at least one cured layer of the resin composition, ¶[0117, 0122], which reads on the claimed primer layer.
Takezawa does not teach applying the LC epoxy composition to a substrate with a surface free energy (SFE) of 50 mN/m or higher and with a surface roughness (Ra) of the substrate facing the primer layer is 1-25 µm.
Tanaka discloses a composition comprising a liquid crystalline monomer with a structure that corresponds to applicant’s (M-2) of instant claim 21, and a curing agent, see abstract and section 2.3, Fig. 1. It is disclosed that a smectic phase with homeotropic alignment is formed on the glass substrates that have surface free energies of 71.3 mN/m and 72.7 mN/m, but only forming a planar alignment on substrates with SFE 46.3 mN/m, (abstract). These surface energies of the substrates are accomplished by surface treatment, section 2.2. This homeotropic alignment resulted in remarkable thermal conductivity measurements compared to thermosetting polymers and ceramic glass, which allows the LC epoxy resin to be applied to high-thermal conductive adhesives (which is a type of primer) and packaging materials in electrical and electronic devices, (abstract).
Roh discloses a thermoelectric element comprising a metal substrate and a resin layer on the metal substrate, abstract. The thermoelectric elements are used in electronic components ¶[0005]. The resin layer can be a mesogenic crystalline epoxy with a curing agent, ¶[0081]. The epoxy resin further contains a first inorganic filler ¶[0010]. The metal substrate has a first region and a second region, where the second region has a higher surface roughness than the first, and the epoxy resin layer is disposed onto the second region, ¶[0009]. Roh further discloses that the surface roughness (Ra) of the second region is 1.05-1.5 times greater than the particle size of the first inorganic filler ¶[0011-0012]. This causes the epoxy resin and filler to be disposed in the grooves formed due to surface roughness, ¶[0016], and the adhesion between the resin layer and the metallic substrate is increased ¶[0092].
Applying the recommended surface roughness to the composition of Takezawa, the boron nitride particles of Takezawa are 0.1-100 µm as stated above, therefore the surface roughness of the metal substrate can be (0.1x1.05)= 0.105 µm minimum to (100x1.5)= 150 µm maximum, which encompasses the claimed range. Takezawa states that the preferable particle size is 0.5-50 µm ¶[0037], which means the preferable surface roughness is (0.5x1.05)=0.525 µm to (50x1.5)= 75 µm, which also encompasses the claimed range.
Takezawa and Tanaka are analogous to the claimed invention because both are in the field of liquid crystalline epoxy resin compositions.
Roh is analogous to the claimed invention because it is in the field of substrates bonded to epoxy resins for use for electronic devices/components.
It would have been obvious to a person having ordinary skill in the art at the time the invention was filed to practice the invention of Takezawa but surface treating the metal substrate to have a surface free energy of 71.3 or 72.7 mN/m because Tanaka teaches that surfaces treated to have the above surface energies produce homeotropic alignment of the LC epoxy monomers and remarkable thermal conductivity is produced, and further forming a surface roughness (Ra) on the metal substrate of 0.105 µm-150 µm (preferably 0.525-75 µm) because the epoxy resin and filler will be disposed in the grooves and increase the adhesion between the resin and substrate as disclosed by Roh.
Regarding claims 11 and 12, the difference between claims 9-10 and 11-12 is the addition of the insulating member over the primer layer.
Takezawa teaches that the composition is used as a heat dissipation material for heat-generating electronic components such as integrated circuit (IC) chips or printed circuit boards, ¶[0086], which are types of semiconductor devices. Takezawa teaches a printed circuit board comprising a wiring layer, a metal plate, and at least one cured layer formed from the LC epoxy composition in the form of a resin layer, a B-stage sheet (semi-cured) or a prepreg disposed between the metal substrate and the wiring layer, ¶[0134]. The LC epoxy resin has boron nitride particles which have an insulating property ¶¶[0003, 0051].
The cured layers, such as the B-stage sheet, of the LC epoxy resin disposed between the metal plate and the circuit board act as an electrical insulator, ¶[0098]. Because multiple layers of the different forms of the LC epoxy resin can be used, the initial layer acts as a primer for the next layer which is the insulating member for the semi-conductor device.
Regarding claims 21-22, 24-26, 28-29, 31, 34-35, Takezawa teaches a composition comprising a liquid crystalline epoxy compound that comprises the structure of general formula (1) and a curing agent ¶[0006] (see ¶[0007] of original document for structure).
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The LC epoxy monomers that conform with general formula (I) are (4-{4-(2,3-epoxypropoxy)phenyl}cyclohexyl-4-(2,3-epoxypropoxy)benzoate and 1-(3-methyl-4-oxiranylmethoxyphenyl)-4-(oxiranylmethoxyphenyl)-1-cyclohexane) ¶[0060]. Each of which is exemplified by applicant in ¶[0039] of the instant specification as a preferred example including the structure M-1 and M-2 respectively.
The LC epoxy monomer is partially polymerized with a curing agent to form a prepolymer ¶[0062]. The pre-polymerization curing agent is hydroquinone ¶¶[0073-0074]. Then a hardening accelerator (additional curing agent) is added to finish curing the epoxy resin, the accelerators are imidazole (cyclic amine) ¶[0075] or triphenylphosphine ¶[0140].
Solvents such as isobutyl alcohol may be added to the composition ¶[0078]. The epoxy resin composition is applied to a metal substrate ¶¶[0086, 0114, 0115, 0117].
Claims 23, 27, 30, 32-33 are rejected under 35 U.S.C. 103 as being unpatentable over Takezawa et al, WO2017122350A1 in view of the ACS article, “Highly Oriented Liquid Crystalline Epoxy Film: Robust High Thermal Conductive Ability,” by Tanaka et al, further in view of Roh et al, WO2019146990 (use US20210091293 for translation and paragraph numbers), as evidenced by Takezawa et al, US20180163015A1.
Regarding claims 23, 27, 30, 32-33, Modified Takezawa teaches the invention according to claims 9 and 21 as explained above. Modified Takezawa does not explicitly teach that the LC epoxy monomers form a smectic domain in the cured resin, but it is stated that the LC epoxy monomer has a mesogenic group ¶[0050], which means it exhibits liquid crystalline behavior and modified Takezawa exemplifies the same monomers as in US20180163015, which does state they form smectic domains, therefore the LC epoxy monomers of modified Takezawa also form smectic domains.
The epoxy resin composition of modified Takezawa has a periodic structure with one period having a length of 2nm to 3nm ¶[0066].
Response to Arguments
Applicant’s arguments with respect to claims 1-20 have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
The double patenting rejections are withdrawn in light of the amendments.
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.
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/V.L.S./Examiner, Art Unit 1766
/RANDY P GULAKOWSKI/Supervisory Patent Examiner, Art Unit 1766