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 .
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 02/09/2024 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Priority
Acknowledgment is made of applicant’s claim for foreign priority submitted on 03/21/2024 under 35 U.S.C. 119 (a)-(d). The certified copy has been placed of record in the file.
Claim Analysis
Summary of Claim 1:
A resin composition, comprising:
(A) 100 parts by weight of a copolymer, the copolymer having
a structural unit formed by a monomer of Formula (1)
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in Formula (1), R1 to R5 are each independently selected from a hydrogen atom, a C1 to C3 alkyl group, a C2 to C3 alkenyl group, a phenyl group, a phenyl group substituted by a C1 to C3 alkyl group, a phenyl group substituted by a C2 to C3 alkenyl group and a C2 to C3 alkenyl phenyl C1 to C3 alkylene group;
and a structural unit formed by a monomer of Formula (2),
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in Formula (2), R6 to R9 are each independently selected from a hydrogen atom, a C1 to C3 alkyl group and a C2 to C3 alkenyl group, and at least one of R6 to R9 is a C2 to C3 alkenyl group;
and the content of the structural unit formed by the monomer of Formula (2) in the copolymer is 55 wt% to 90 wt%;
and
(B) 1 part by weight to 15 parts by weight of a compound of Formula (3);
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in Formula (3), each X’, Y’ and Z’ independently represent a hydrogen atom, a C1 to C4 alkyl group, a phenyl group, or an unsaturated C=C double bond-containing group.
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.
Claims 1,2,4,7-16 are rejected under 35 U.S.C. 103 as being unpatentable over Luo et al. (WO 2024/130761 A1, machine translation; hereinafter as “Luo”) in view of Dukette et al. (“Conformation of Intramolecularly Cross-Linked Polymer Nanoparticles on Solid Substrates”, Nano Letters, 2005, Vol. 5, No. 9, 1704-1709; hereinafter “Dukette”) as further evidenced by Chen et al. (“Effect of the composition ratio of repeating units on the properties of poly(4‑vinylbenzocyclobutene‑co‑styrene): molecular dynamics simulation studies”, Journal of Polymer Research, 2023, Vol. 30, article number 316; hereinafter “Chen-JPR”).
Regarding claim 1: Luo teaches a benzocyclobutene resin (page 3, [0010]), comprising at least one structural unit A and at least one structural unit B; the structural unit A has a structure as shown in Formula I (page 3, [0011]).
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Formula I
In Formula I, R1 is vinylidene and/or ethylene (page 3, [0012]). The structural unit A is similar to Formula (2) of instant application but does not teach the exact structure of Formula (2).
The structural unit B has a structure as shown in Formula II (page 3, [0014]).
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Formula II
In Formula II, R2 is vinyl, ethyl and/or phenyl (page 3, [0015]). When R2 is phenyl, the structural unit B corresponds to the structure of Formular (1) of instant application (R1 to R5 are all hydrogen atoms). Luo also specifies that the benzocyclobutene resin comprises a structural unit B3, the structural unit B3 has a structure as shown in Formula IIC, and a side chain thereof contains phenyl, and has good compatibility with other resins (page 4, [0030] and [0031]).
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Formula IIC
Formular IIC corresponds to the structure of Formula (1) of instant application (R1 to R5 are all hydrogen atoms).
Luo also teaches that the molar percentage of the structural unit A in the benzocyclobutene resin is 5-80%, further preferably 30-60%, and the molar percentage of the structural unit B is 15-90%, further preferably 30-70%, so that the benzocyclobutene resin has excellent dielectric properties, heat resistance, modulus and mechanical properties, and a higher heat curing crosslinking reaction activity and crosslinking density (page 4, [0024]).
To convert the molar percentage (mol%) to weight percentage (wt%) used in instant application, the following structural unit A, B, mol% ranges and molecular weight (MW) parameters are used.
Structure unit A:
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When R1 is vinylidene
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, MW = 156 g/mol.
The structural unit A in the benzocyclobutene resin, as Luo teaches, is in the preferred range, 30-60 mol%.
Structure unit B:
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, MW = 104 g/mol
The structural unit B in the benzocyclobutene resin is in the range 40-70 mol%, correspondingly.
When A is at 60 mol% and B is at 40 mol%,
A wt% = (156*60)/(156*60+104*40) * 100% = 69.2 wt%
When A is at 30 mol% and B is 70% mol%,
A wt% = (156*30)/(156*30+104*70) * 100% = 39.1 wt%
Therefore, Luo teaches that the weight percentage of the structural unit A in the in the benzocyclobutene resin is preferably 39.1 wt% to 69.2 wt%, which overlaps with the content of the structural unit formed by the benzocyclobutene-containing monomer of Formula (2) in the copolymer (55 wt% to 90 wt%, claim 1, instant application).
Luo does not expressly teach the exact structure of unit formed by a monomer of Formula (2) of instant application.
However, Dukette teaches a linear copolymer consisting of styrene monomer (monomer of Formula (1) of instant application, where R1 to R5 are all hydrogen atoms) and styrene monomer containing a pendent cross-linking group (benzocyclobutene, BCB) (monomer of Formula (2) of instant application, where R6, R7 and R9 are hydrogen atoms and R8 is vinyl ) (page 1704, last paragraph to page 1705, 1st paragraph; Figure 1), wherein the copolymer (sample E-PS33K in Table 1) comprises 60 mol% of the BCB containing monomer. To convert the molar percentage (mol%) to weight percentage (wt%) used in instant application, the following structural units, mol% ranges and molecular weight (MW) parameters are used.
Styrene (St), MW 104g/mol, 40 mol%.
BCB containing monomer (i.e., 4-vinylbenzocyclobutene, “VBCB”), MW 130 g/mol, 60 mol%.
The weight percentage content of VBCB in the copolymer is calculated as below.
VBCB wt% = (130*60)/(130*60 + 104*40) * 100% = 65 wt%
The VBCB content (65 wt%) in the copolymer sample E-PS33K by Dukette encompasses the instant application ranges (the content of the structural unit formed by the monomer of Formula (2) in the copolymer is 55 wt% to 90 wt%). As further evidenced, Chen-JPR teaches an increase of VBCB content in St-VBCB copolymer increases the crosslinking density, glass temperature of the resin material, decreases thermal expansion (Abstract, Figures 11 and 12).
In an analogous art of polymer resins comprising benzocyclobutene group, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the benzocyclobutene resin by Luo, so as to incorporate St-VBCB copolymers with VBCB content from higher than 55 wt% as taught by Dukette, and would have been motivated to do so with reasonable expectation that this would achieve an increase in glass transition temperature and a decrease in thermal expansion as suggested by Dukette as further evidenced by Chen-JPR.
Luo also teaches that the resin composition further comprises an initiator (page 7, [0069]), which includes a carbon-based radical initiator (page 7, [0070]), e.g., dicumene (page 7, [0072]). Dicumene (2,3-Dimethyl-2,3-diphenylbutane, CAS No.1889-67-4) has the following structure, which corresponds to the compound of Formula (3) (X’=Y’=Z’=hydrogen atom) in instant application.
Dicumene structure:
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Luo also teaches for 100 pars by weight of the mass of the benzocyclobutene resin, the weight of initiator is 0.1 to 3 parts (page 7, [0070]), which overlaps the range “1 part by weight to 15 parts by weight of a compound of Formula (3)” in instant application.
Regarding claim 2: The disclosure of Luo in view of Dukette is adequately set forth in paragraph above and is incorporated herein by reference. Dukette teaches the monomer of Formula (1-1) (i.e., styrene) and monomer of Formula (2-1) (i.e., 4-vinylbenzocyclobutene) (page 1704, last paragraph to page 1705, 1st paragraph; Figure 1).
Regarding claim 4: The disclosure of Luo in view of Dukette is adequately set forth in paragraph above and is incorporated herein by reference. Dukette teaches the copolymer is a random copolymer (page 1704, last paragraph to page 1705, 1st paragraph; Figure 1).
Regarding claim 7: The disclosure of Luo in view of Dukette is adequately set forth in paragraph above and is incorporated herein by reference.
Luo teaches the resin composition further comprises an initiator (page 7, [0069]), which includes a carbon-based radical initiator (page 7, [0070]), e.g., dicumene (page 7, [0072]). Dicumene (2,3-Dimethyl-2,3-diphenylbutane, CAS No.1889-67-4) has the following structure, which corresponds to the compound of Formula (3) (X’=Y’=Z’=hydrogen atom) in instant application.
Dicumene structure:
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Regarding claim 8: The disclosure of Luo in view of Dukette is adequately set forth in paragraph above and is incorporated herein by reference. Luo teaches the resin composition can be in combination with other thermosetting components containing unsaturated groups (C ═ C double bonds) (page 6, [0054]), selected from, for example, triallyl cyanurate and triallyl isocyanurate (page 6, [0062]), divinylbenzene, multifunctional acrylate and P, P’-divinyl -1,2-diphenylethane (BVPE). (page 7, [0063]).
Regarding claim 9: The disclosure of Luo in view of Dukette is adequately set forth in paragraph above and is incorporated herein by reference. Luo teaches the resin composition further comprises, a polyolefine different from the copolymer, a maleimide resin (page 6, [0059]), or an unsaturated group-terminated polyphenyleneether resin (page 6, [0061]).
Regarding claim 10: The disclosure of Luo in view of Dukette is adequately set forth in paragraph above and is incorporated herein by reference. Luo teaches that the resin composition comprises an inorganic filler (page 7, [0075]), a flame retardant (page 8, [0085]), a curing accelerator different from the compound of Formula (3) (e.g., curing initiator, page 7, [0072]), a solvent (page 8, [0088]), or a silane coupling agent (page 8, [0083]).
Regarding claim 11: The disclosure of Luo in view of Dukette is adequately set forth in paragraph above and is incorporated herein by reference. Luo teaches a prepreg (page 8, [0095]), a laminate (page 9, [0102]), or a printed circuit board (page 12, [0155]) made from the resin composition.
Regarding claim 12-16: The disclosure of Luo in view of Dukette is adequately set forth in paragraph above and is incorporated herein by reference. Luo in view of Dukette does not expressly teach the following properties.
Glass transition temperature as measured by reference to IPC-TM-650 2.4.24.4
Storage modulus decay rate as measured and calculated by reference to IPC-TM-650 2.4.24.4
Reflow warpage magnitude as measured by reference to JESD22-B112A
Thermal expansion in Z-axis as measured by reference to IPC-TM-650 2.4.24.5
Dissipation factor as measured by reference to JIS C2565
However, since the combination of Luo in view of Dukette teaches substantially identical resin composition as the recited claimed, one of ordinary skill in the art before the effective filing date of the claimed invention was made that the above claimed effects and physical properties, would be expected to be the same as claimed (i.e., a glass transition temperature as measured by reference to IPC-TM-650 2.4.24.4 of greater than or equal to 290oC, a storage modulus decay rate as measured and calculated by reference to IPC-TM-650 2.4.24.4 of less than or equal to 16%, a reflow warpage magnitude as measured by reference to JESD22-B112A of less than or equal to 14 μm, a percent of thermal expansion in Z-axis as measured by reference to IPC-TM-650 2.4.24.5 of less than or equal to 1.2%, and dissipation factor as measured by reference to JIS C2565 at 10 GHz of less than or equal to 0.00086). If there is any difference between the product of Luo in view of Dukette and the product of the instant claims the difference would have been minor and obvious. “Products of identical chemical composition cannot have mutually exclusive properties.” A chemical composition and its properties are inseparable. Therefore, if the prior art teaches the identical composition, the properties applicant discloses and/or claims are necessarily present. See MPEP 2112.01(I). Absent an objective showing to the contrary, the addition of the claimed physical properties to the claim language fails to provide patentable distinction over the prior art.
"Where ... the claimed and prior art products are identical or substantially identical ... the PTO can require an applicant to prove that the prior art products do not necessarily or inherently possess the characteristics of his claimed product." In re Best, 562 F.2d 1252, 1255 (CCPA 1977) (citations and footnote omitted). The mere recitation of a property or characteristic not disclosed by the prior art does not necessarily confer patentability to a composition or a method of using that composition. See In re Skoner, 51 7 F .2d 94 7, 950 ( CCP A 197 5).
Claims 5-6 are rejected under 35 U.S.C. 103 as being unpatentable over
Luo et al. (WO 2024/130761 A1, machine translation; hereinafter as “Luo”) in view of Dukette et al. (“Conformation of Intramolecularly Cross-Linked Polymer Nanoparticles on Solid Substrates”, Nano Letters, 2005, Vol. 5, No. 9, 1704-1709; hereinafter “Dukette”) as applied to claim 1 above, and further in view of Chen et al. (CN 109734959 A, published 05/10/2019, machine translation; hereinafter “Chen’959”).
Regarding claims 5 and 6: The disclosure of Luo in view of Dukette is adequately set forth in paragraph 5 above and is incorporated herein by reference. Luo teaches a benzocyclobutene resin comprising dicumene as a carbon-based radical initiator. Luo in view of Dukette does not expressly teach Formula (3) having at least one unsaturated C=C double bond-containing group.
However, Chen’959 teaches a temperature-resistant free radical initiator, 2, 3-dimethyl-2, 3-di (4-vinylphenyl) butane (page 8, [0044, 0045]), corresponding to Formula (3-5) of instant application, which reads on the limitation of claim 5 “where in the compound of Formula (3) has at least one unsaturated C=C double bond-containing group”, and the limitation of claim 6 “wherein, in Formula (3), at least one of X’, Y’ and Z’ represents a vinyl group, a vinylbenzyl group, a vinylphenyl group, an allyl group or a (meth)acryloyloxy group” (i.e., Z’ is a vinyl group).
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Chen’959 further teaches that compared with broadly used free radical initiator 2, 3-dimethyl-2, 3-diphenylbutane (also known as dicumene, Formula (3-1) of instant application) (page 3, [0020]), the temperature-resistant free radical initiator (e.g., 2, 3-dimethyl-2, 3-di (4-vinylphenyl) butane) has better temperature resistance, and can meet downstream applications with higher requirements on temperature (page 6, [0033]).
In an analogous art of polymer resins comprising free radical initiators, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the dicumene as a carbon-based radical initiator by Luo, so as to include , 3-dimethyl-2, 3-di (4-vinylphenyl) butane) as taught by Chen’959 and would have been motivated to do so with reasonable expectation that this would result in providing carbon-based radical initiator to improve its temperature resistance in the resin as suggested by Chen’959 (page 6, [0033]).
Allowable Subject Matter
Claim 3 is objected to as being dependent upon a rejected base claim 1, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter:
Claim 3 would be allowable for disclosing the copolymer structures comprising a copolymer of Formula (4) to a copolymer Formula (19) or a combination thereof, wherein m, n, x, y and z are each independently a positive integer, 2≦m≦44, 12≦n≦70, 2≦x+z≦44, and 12≦y≦70.
The combination of Luo in view of Dukette does not expressly teach the values (m, n) of degree of polymerization (DP) as claimed “2≦m≦44, 12≦n≦70”. Therefore, the instant claim 3 is distinguished over the prior art.
Conclusion
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/HAOPENG WANG/Examiner, Art Unit 1763
/JOSEPH S DEL SOLE/Supervisory Patent Examiner, Art Unit 1763
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