DETAILED ACTION
Applicant’s response filed on 09/26/2025 has been fully considered. Claims 1-4 and 6-19 are pending. Claims 1-3, 6, 8, 9, and 19 are amended. Claim 5 is canceled.
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 .
Priority
Applicant’s claim for the benefit of a prior-filed application under 35 U.S.C. 119(e) or under 35 U.S.C. 120, 121, 365(c), or 386(c) is acknowledged.
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Claim Rejections - 35 USC § 103
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 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 1-4 and 6-19 are rejected under 35 U.S.C. 103 as being unpatentable over Qiu et al. (CN 114805802 A, machine translation in English or untranslated patent used for citation as indicated) in view of Takano et al. (JP 2017-165827 A, machine translation in English used for citation).
Regarding claim 1, Qiu teaches a benzoxazine-terminated imide that is obtained by reacting diamine-terminated imide as amine source with monohydric phenol and paraformaldehyde (translation p. 4, l. 23-24), wherein the benzoxazine end-capped imide has the following structure: (translation p. 4, l. 29)
PNG
media_image1.png
150
632
media_image1.png
Greyscale
(untranslated [0012]), wherein n=1~5 (translation p. 4, l. 30),
PNG
media_image2.png
100
94
media_image2.png
Greyscale
(untranslated [0014]) represents a residual group derived from a dianhydride monomer (translation p. 4, l. 31),
PNG
media_image3.png
92
100
media_image3.png
Greyscale
(untranslated [0014]) represents a residual group derived from a diamine monomer (translation p. 4, l. 32-33), and
PNG
media_image4.png
92
102
media_image4.png
Greyscale
(untranslated [0014]) represents a residual group derived from a monohydric phenol (translation p. 4, l. 32), wherein the diamine-terminated imide is obtained by thermal cyclization of small molecular polyamic acid in an inert gas (translation p. 4, l. 25-26), wherein the small molecular polyamic acid is prepared by condensation reaction of dianhydride monomer and diamine monomer (translation p. 4, l. 27-28), wherein the diamine-terminated imide has the following structural formula: (translation p. 4, l. 33)
PNG
media_image5.png
156
560
media_image5.png
Greyscale
(untranslated [0016]), wherein the diamine monomer is hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, or 1,4-butanediamine (translation p. 5, l. 4-5), wherein the molar ratio of the amine monomer to the dianhydride monomer is 1:1 to 2:1 (p. 5, l. 20-21), which reads on a resin composition, comprising: benzoxazine, wherein the benzoxazine is synthesized from a primary amine-capped flexible polyimide oligomer, an aldehyde, and a monofunctional phenolic compound, the primary amine-capped flexible polyimide oligomer is a reaction product of a tetracarboxylic acid dianhydride and a flexible diamine, and a molar ratio of dianhydride in the tetracarboxylic acid dianhydride to the flexible diamine is 1:(1-2).
Qiu does not teach that the resin composition further comprises a resin mixture, wherein the resin mixture comprises one or more of an epoxy resin, a maleimide resin, and a cyanate ester resin containing two or more functional groups, and the resin mixture is 0.5%-50% by weight of the benzoxazine. However, Takano teaches a cyanate ester compound (p. 4, l. 11) having two, three, four cyanate groups (p. 8, l. 5-p. 9, l. 1), a maleimide compound (p. 4, l. 12) having two maleimide groups (p. 9, l. 38-42), and an epoxy resin (p. 4, l. 34) having two or more epoxy groups (p. 11, l. 11-12), that are present in a resin composition further comprising a benzoxazine compound (p, 4, l. 11), wherein the content of the benzoxazine compound in the resin composition is 1 to 25 parts by mass with respect to 100 parts by mass of the resin solid content (p. 4, l. 27-28; p. 6, l. 5-6), the content of the cyanate ester compound in the resin composition is 1 to 90 parts by mass with respect to 100 parts by mass of the resin solid content (p. 9, l. 32-35), and the content of the maleimide compound in the resin composition is 1 to 90 parts by mass with respect to 100 parts by mass of the resin solid content (p. 10, l. 7-10), which means that the content of the cyanate ester compound is from 1 / 25 * 100% = 4% to 90 / 1 * 100% = 9000% by weight of the benzoxazine, that the content of the maleimide compound is from 1 / 25 * 100% = 4% to 90 / 1 * 100% = 9000% by weight of the benzoxazine, and that the content of the epoxy resin is greater than 0% by weight of the benzoxazine. Qiu and Takano are analogous art because both references are in the same field of endeavor of a resin composition comprising benzoxazine. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to combine Takano’s cyanate ester compound having two, three, four cyanate groups, maleimide compound having two maleimide groups, and/or epoxy resin having two or more epoxy groups with Qiu’s benzoxazine-terminated imide, and to optimize the total content of Takano’s cyanate ester compound, maleimide compound, and/or epoxy resin to be from 4 to 50 parts by mass with respect to 100 parts by mass of Qiu’s benzoxazine-terminated imide. The proposed modification would read on the resin composition further comprising a resin mixture, wherein the resin mixture comprises one or more of an epoxy resin, a maleimide resin, and a cyanate ester resin containing two or more functional groups, and the resin mixture is 4%-50% by weight of the benzoxazine as claimed. One of ordinary skill in the art would have been motivated to do so because Takano teaches that the cyanate ester compound (p. 4, l. 11) having two, three, four cyanate groups (p. 8, l. 5-p. 9, l. 1) is beneficial for providing a cured resin product with excellent characteristics such as glass transition temperature, low thermal expansion property, and plating adhesion (p. 9, l. 30-31), that the cyanate ester compound is beneficial for being useful at a content that is 1 to 90 parts by mass with respect to 100 parts by mass of the resin solid content in a resin composition (p. 9, l. 32-35), that the maleimide compound (p. 4, l. 12) having two maleimide groups (p. 9, l. 38-42) is beneficial for being useful at a content in the range of 1 to 90 parts by mass with respect to 100 parts by mass of the resin solid content in a resin composition (p. 10, l. 7-10), that this content is beneficial for providing a resin composition that is excellent in glass transition temperature (p. 10, l. 10-11), that the epoxy resin (p. 4, l. 34) having two or more epoxy groups (p. 11, l. 11-12) is beneficial for providing flame retardancy and heat resistance (p. 11, l. 24-25), and that they are beneficial for being useful in a resin composition further comprising a benzoxazine compound (p, 4, l. 11) at a content that is 1 to 25 parts by mass with respect to 100 parts by mass of the resin solid content in the resin composition (p. 4, l. 27-28; p. 6, l. 5-6), which would have been desirable for Qiu’s invention because Qiu teaches a benzoxazine-terminated imide (translation p. 4, l. 23-24), that it has a glass transition temperature (translation p. 5, l. 35-36; p. 7, l. 24-26; p. 8, l. 16-18; p. 9, l. 10-12; p. 10, l. 5-7), that it has flame retardancy (translation p. 4, l. 19-21; p. 5, l. 35-p. 6, l. 2; p. 7, l. 24-26; p. 8, l. 16-18; p. 9, l. 10-12; p. 10, l. 5-7), and that cured polybenzoxazine has heat resistance (translation p. 3, l. 27-28), which means that the total content of Takano’s cyanate ester compound, maleimide compound, and/or epoxy resin in parts by mass with respect to 100 parts by mass of Qiu’s benzoxazine-terminated imide would have affected glass transition temperature, flame retardancy, and/or heat resistance of the resulting composition, which means that optimizing the total content of Takano’s cyanate ester compound, maleimide compound, and/or epoxy resin in parts by mass with respect to 100 parts by mass of Qiu’s benzoxazine-terminated imide would have been beneficial for optimizing glass transition temperature, flame retardancy, and/or heat resistance of the resulting composition.
Qiu does not teach with sufficient specificity that a molar ratio of dianhydride in the tetracarboxylic acid dianhydride to the flexible diamine is 1:(1.01-1.1). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize Qiu’s molar ratio of Qiu’s amine monomer to Qiu’s dianhydride monomer to be 1.01:1 to 1.1:1. The proposed modification would read on wherein a molar ratio of dianhydride in the tetracarboxylic acid dianhydride to the flexible diamine is 1:(1.01-1.1) as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for optimizing a yield of Qiu’s diamine-terminated imide from Qiu’s dianhydride monomer and Qiu’s diamine monomer because Qiu teaches that a molar ratio of dianhydride in the tetracarboxylic acid dianhydride to the flexible diamine is 1:(1-2), that the small molecular polyamic acid is prepared by condensation reaction of dianhydride monomer and diamine monomer (translation p. 4, l. 27-28), and that the diamine-terminated imide is obtained by thermal cyclization of small molecular polyamic acid in an inert gas (translation p. 4, l. 25-26), which means that Qiu’s molar ratio of Qiu’s amine monomer to Qiu’s dianhydride monomer would have affected a yield of Qiu’s diamine-terminated imide from Qiu’s dianhydride monomer and Qiu’s diamine monomer.
Regarding claim 2, Qiu teaches that the benzoxazine-terminated imide is obtained by reacting diamine-terminated imide as amine source with monohydric phenol and paraformaldehyde (translation p. 4, l. 23-24), that the benzoxazine end-capped imide has the following structure: (translation p. 4, l. 29)
PNG
media_image1.png
150
632
media_image1.png
Greyscale
(untranslated [0012]), wherein n=1~5 (translation p. 4, l. 30),
PNG
media_image2.png
100
94
media_image2.png
Greyscale
(untranslated [0014]) represents a residual group derived from a dianhydride monomer (translation p. 4, l. 31),
PNG
media_image3.png
92
100
media_image3.png
Greyscale
(untranslated [0014]) represents a residual group derived from a diamine monomer (translation p. 4, l. 32-33), and
PNG
media_image4.png
92
102
media_image4.png
Greyscale
(untranslated [0014]) represents a residual group derived from a monohydric phenol (translation p. 4, l. 32), that the diamine-terminated imide is obtained by thermal cyclization of small molecular polyamic acid in an inert gas (translation p. 4, l. 25-26), that the small molecular polyamic acid is prepared by condensation reaction of dianhydride monomer and diamine monomer (translation p. 4, l. 27-28), that the dianhydride monomer is benzophenone tetracarboxylic dianhydride, 3,3',4,4'-diphenyl ether tetracarboxylic dianhydride, or 3,3',4,4'-diphenylsulfone dianhydride (translation p. 4, l. 35-p. 5, l. 2), that the diamine monomer is hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, or 1,4-butanediamine (translation p. 5, l. 4), and that the monohydric phenol (translation p. 4, l. 24) is phenol (translation p. 6, l. 34; p. 7, l. 12, 30; p. 8, l. 4; p. 9, l. 16, 30), which reads on wherein a molecular formula of the benzoxazine is shown as claimed, wherein R1, R2, R3, and R4 are each independently selected from -H, and at least one of R1, R2, R3, and R4 is -H, X1 is an alkylene containing a long chain structure in main chain, and X2 is one or more selected from ether group, carbonyl, and sulfone group as claimed.
Regarding claim 3, Qiu teaches that the benzoxazine-terminated imide is obtained by reacting diamine-terminated imide as amine source with monohydric phenol and paraformaldehyde (translation p. 4, l. 23-24), that the diamine-terminated imide is obtained by thermal cyclization of small molecular polyamic acid in an inert gas (translation p. 4, l. 25-26), that the small molecular polyamic acid is prepared by condensation reaction of dianhydride monomer and diamine monomer (translation p. 4, l. 27-28), that
PNG
media_image3.png
92
100
media_image3.png
Greyscale
(untranslated [0014]) represents a residual group derived from a diamine monomer (translation p. 4, l. 32-33), and that the diamine monomer is hexamethylenediamine (translation p. 5, l. 4), which reads on wherein X1 is an alkylene containing 6 carbon atoms as claimed.
Regarding claim 4, Qiu teaches that the benzoxazine-terminated imide is obtained by reacting diamine-terminated imide as amine source with monohydric phenol and paraformaldehyde (translation p. 4, l. 23-24), that the diamine-terminated imide has the following structural formula: (translation p. 4, l. 33)
PNG
media_image5.png
156
560
media_image5.png
Greyscale
(untranslated [0016]), that n=1~5 (translation p. 4, l. 30), that
PNG
media_image2.png
100
94
media_image2.png
Greyscale
(untranslated [0014]) represents a residual group derived from a dianhydride monomer (translation p. 4, l. 31), that
PNG
media_image3.png
92
100
media_image3.png
Greyscale
(untranslated [0014]) represents a residual group derived from a diamine monomer (translation p. 4, l. 32-33), that the diamine-terminated imide is obtained by thermal cyclization of small molecular polyamic acid in an inert gas (translation p. 4, l. 25-26), that the small molecular polyamic acid is prepared by condensation reaction of dianhydride monomer and diamine monomer (translation p. 4, l. 27-28), that the dianhydride monomer is 4,4'-(4,4'-isopropyldiphenoxy)diphthalic anhydride, bisphenol A dianhydride, 3,3',4,4'-diphthalic anhydride, benzophenone tetracarboxylic dianhydride, cyclobutane tetracarboxylic dianhydride, 3,3',4,4'-diphenyl ether tetracarboxylic dianhydride, 4,4'-(hexafluoroisopropene)diphthalic anhydride, 3,3',4,4'-diphenylsulfone dianhydride, or 3,6-bis(methoxy)phthalic anhydride (p. 4, l. 35-p. 5, l. 3), and that the diamine monomer is hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, 1,4-butanediamine, p-phenylenediamine, m-phenylenediamine, 4, 4'-diaminodiphenyl ether, 2,2'-bis-trifluoromethyl-4,4'-diaminodiphenyl ether, 1,4-bis(4-aminophenoxy)benzene, 1,4-bis(4'-amino-2'-trifluoromethylphenoxy)benzene, 1,4-bis(4'-amino-3'-trifluoromethylphenoxy)benzene, 4,4'-diaminodiphenylmethane, 2,3'-diaminodiphenylmethane, 2,4'-diaminodiphenylmethane, or 4,4'-diaminobenzophenone (translation p. 5, l. 4-10), which reads on wherein the primary amine-capped flexible polyimide oligomer has a number-average molecular weight of 256-4,992, which reads on the claimed range. The number-average molecular weight is based on the calculations 12.011 * 10 + 1.00784 * 16 + 15.999 * 4 + 14.0067 * 4 = 256 and 12.011 * 275 + 1.00784 * 164 + 15.999 * 42 + 14.0067 * 12 + 18.9984 * 36 = 4992.
Regarding claim 6, Qiu teaches that the dianhydride monomer is one or more of 4,4'-(4,4'-isopropyldiphenoxy)diphthalic anhydride, 3,3',4,4'-diphthalic anhydride, benzophenone tetracarboxylic dianhydride, 3,3',4,4'-diphenyl ether tetracarboxylic dianhydride, and 4,4'-(hexafluoroisopropene)diphthalic anhydride (translation p. 4, l. 35-p. 5, l. 3), which reads on wherein the tetracarboxylic acid dianhydride is selected from the group consisting of 3,3’-4.4’-biphenyltetracarboxylic dianhydride, 4,4’-oxydiphthalic anhydride, 3,3’,4,4’-benzophenonetetracarboxylic dianhydride, 4,4’-(hexafluoroisopropylidene)diphthalic anhydride, 4,4’-(4,4’-isopropylidenediphenoxy)bis(phthalic anhydride), and a combination thereof as claimed.
Regarding claim 7, Qiu teaches that the diamine monomer is one of hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, 1,4-butanediamine, p-phenylenediamine, m-phenylenediamine, 4, 4'-diaminodiphenyl ether, 2,2'-bis-trifluoromethyl-4,4'-diaminodiphenyl ether, 1,4-bis(4-aminophenoxy)benzene, 1,4 -bis(4'-amino-2'-trifluoromethylphenoxy)benzene, 1,4-bis(4'-amino-3'-trifluoromethylphenoxy)benzene, 4,4'-diaminodiphenylmethane, 2,3'-diaminodiphenylmethane, 2,4'-diaminodiphenylmethane, 4,4'-diaminobenzophenone, or derivatives of the above diamines (translation p. 5, l. 4-10), and that the diamine monomer can also be hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, 1,4-butanediamine, p-phenylenediamine, m-phenylenediamine, 4,4'-diaminodiphenyl ether, 2,2'-bis-trifluoromethyl-4,4'-diaminodiphenyl ether, 1,4-bis(4-aminophenoxy)benzene, 1,4-bis(4'-amino-2'-trifluoromethylphenoxy)benzene, 1,4-bis(4'-amino-3'-trifluoromethylphenoxy)benzene, 4,4 '-diaminodiphenylmethane, 2,3'-diaminodiphenylmethane, 2,4'-diaminodiphenylmethane, 4,4'-diaminobenzophenone, derivatives of the above diamines, or more than one (translation p. 10, l. 14-20), which suggests selecting Qiu’s hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, or 1,4-butanediamine and Qiu’s p-phenylenediamine, m-phenylenediamine, 4, 4'-diaminodiphenyl ether, 2,2'-bis-trifluoromethyl-4,4'-diaminodiphenyl ether, 1,4-bis(4-aminophenoxy)benzene, 1,4 -bis(4'-amino-2'-trifluoromethylphenoxy)benzene, 1,4-bis(4'-amino-3'-trifluoromethylphenoxy)benzene, 4,4'-diaminodiphenylmethane, 2,3'-diaminodiphenylmethane, 2,4'-diaminodiphenylmethane, or 4,4'-diaminobenzophenone as Qiu’s diamine monomer, which suggests wherein the flexible diamine is a mixture of a diamine containing a flexible long chain in main chain and an aromatic diamine, and a molar ratio of the diamine containing a flexible long chain in main chain to the aromatic diamine is (0:10)-(10:0).
Qiu does not teach a specific embodiment wherein the flexible diamine is a mixture of a diamine containing a flexible long chain in main chain or side chain and an aromatic diamine, and does not teach that a molar ratio of the diamine containing a flexible long chain in main chain or side chain to the aromatic diamine is (1:9)-(10:0). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Qiu’s hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, or 1,4-butanediamine and Qiu’s p-phenylenediamine, m-phenylenediamine, 4, 4'-diaminodiphenyl ether, 2,2'-bis-trifluoromethyl-4,4'-diaminodiphenyl ether, 1,4-bis(4-aminophenoxy)benzene, 1,4 -bis(4'-amino-2'-trifluoromethylphenoxy)benzene, 1,4-bis(4'-amino-3'-trifluoromethylphenoxy)benzene, 4,4'-diaminodiphenylmethane, 2,3'-diaminodiphenylmethane, 2,4'-diaminodiphenylmethane, or 4,4'-diaminobenzophenone as Qiu’s diamine monomer, and to optimize a molar ratio of Qiu’s hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, or 1,4-butanediamine to Qiu’s p-phenylenediamine, m-phenylenediamine, 4, 4'-diaminodiphenyl ether, 2,2'-bis-trifluoromethyl-4,4'-diaminodiphenyl ether, 1,4-bis(4-aminophenoxy)benzene, 1,4 -bis(4'-amino-2'-trifluoromethylphenoxy)benzene, 1,4-bis(4'-amino-3'-trifluoromethylphenoxy)benzene, 4,4'-diaminodiphenylmethane, 2,3'-diaminodiphenylmethane, 2,4'-diaminodiphenylmethane, or 4,4'-diaminobenzophenone to be from 1:9 to 10:0. The proposed modification would read on wherein the flexible diamine is a mixture of a diamine containing a flexible long chain in main chain and an aromatic diamine, and a molar ratio of the diamine containing a flexible long chain in main chain to the aromatic diamine is (1:9)-(10:0) as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying mechanical properties of Qiu’s benzoxazine-terminated imide and for optimizing the mechanical properties of Qiu’s benzoxazine-terminated imide because Qiu teaches that the diamine monomer is one of hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, 1,4-butanediamine, p-phenylenediamine, m-phenylenediamine, 4, 4'-diaminodiphenyl ether, 2,2'-bis-trifluoromethyl-4,4'-diaminodiphenyl ether, 1,4-bis(4-aminophenoxy)benzene, 1,4 -bis(4'-amino-2'-trifluoromethylphenoxy)benzene, 1,4-bis(4'-amino-3'-trifluoromethylphenoxy)benzene, 4,4'-diaminodiphenylmethane, 2,3'-diaminodiphenylmethane, 2,4'-diaminodiphenylmethane, 4,4'-diaminobenzophenone, or derivatives of the above diamines (translation p. 5, l. 4-10), that the diamine monomer can also be hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, 1,4-butanediamine, p-phenylenediamine, m-phenylenediamine, 4,4'-diaminodiphenyl ether, 2,2'-bis-trifluoromethyl-4,4'-diaminodiphenyl ether, 1,4-bis(4-aminophenoxy)benzene, 1,4-bis(4'-amino-2'-trifluoromethylphenoxy)benzene, 1,4-bis(4'-amino-3'-trifluoromethylphenoxy)benzene, 4,4 '-diaminodiphenylmethane, 2,3'-diaminodiphenylmethane, 2,4'-diaminodiphenylmethane, 4,4'-diaminobenzophenone, derivatives of the above diamines, or more than one (translation p. 10, l. 14-20), that the benzoxazine-terminated imide is obtained by reacting diamine-terminated imide as amine source with monohydric phenol and paraformaldehyde (translation p. 4, l. 23-24), that the diamine-terminated imide is obtained by thermal cyclization of small molecular polyamic acid in an inert gas (translation p. 4, l. 25-26), and that the small molecular polyamic acid is prepared by condensation reaction of dianhydride monomer and diamine monomer (translation p. 4, l. 27-28), which means that Qiu’s benzoxazine-terminated imide would comprise flexible segments due to the presence of Qiu’s hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, or 1,4-butanediamine because they are aliphatic diamines, that Qiu’s benzoxazine-terminated imide would further comprise rigid segments due to the presence of Qiu’s p-phenylenediamine, m-phenylenediamine, 4, 4'-diaminodiphenyl ether, 2,2'-bis-trifluoromethyl-4,4'-diaminodiphenyl ether, 1,4-bis(4-aminophenoxy)benzene, 1,4 -bis(4'-amino-2'-trifluoromethylphenoxy)benzene, 1,4-bis(4'-amino-3'-trifluoromethylphenoxy)benzene, 4,4'-diaminodiphenylmethane, 2,3'-diaminodiphenylmethane, 2,4'-diaminodiphenylmethane, or 4,4'-diaminobenzophenone because they are aromatic diamines, and that the presence of flexible segments and rigid segments would provide flexibility and strength to Qiu’s benzoxazine-terminated imide, which means that a molar ratio of Qiu’s hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, or 1,4-butanediamine to Qiu’s p-phenylenediamine, m-phenylenediamine, 4, 4'-diaminodiphenyl ether, 2,2'-bis-trifluoromethyl-4,4'-diaminodiphenyl ether, 1,4-bis(4-aminophenoxy)benzene, 1,4 -bis(4'-amino-2'-trifluoromethylphenoxy)benzene, 1,4-bis(4'-amino-3'-trifluoromethylphenoxy)benzene, 4,4'-diaminodiphenylmethane, 2,3'-diaminodiphenylmethane, 2,4'-diaminodiphenylmethane, or 4,4'-diaminobenzophenone would have affected the mechanical properties of Qiu’s benzoxazine-terminated imide.
Regarding claim 8, Qiu teaches that the diamine monomer is one of hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, 1,4-butanediamine, p-phenylenediamine, m-phenylenediamine, 4, 4'-diaminodiphenyl ether, or 1,4-bis(4-aminophenoxy)benzene (translation p. 5, l. 4-10), and that the diamine monomer can also be hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, 1,4-butanediamine, p-phenylenediamine, m-phenylenediamine, 4,4'-diaminodiphenyl ether, or more than one (translation p. 10, l. 14-20), which suggests selecting Qiu’s hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, or 1,4-butanediamine and Qiu’s p-phenylenediamine, m-phenylenediamine, 4, 4'-diaminodiphenyl ether, or 1,4-bis(4-aminophenoxy)benzene as Qiu’s diamine monomer, which suggests wherein a molecular formula of the diamine containing a flexible long chain in main chain or side chain is shown as follows: H2N-X3-NH2, wherein X3 is an alkylene containing a long chain structure in main chain, and the aromatic diamine is selected from m-phenylenediamine 4,4’-diaminodiphenyl ether, p-phenylenediamine, and 1,4-bis(4-aminophenoxy)benzene.
Qiu does not teach a specific embodiment wherein a molecular formula of the diamine containing a flexible long chain in main chain or side chain is shown as claimed, and the aromatic diamine is selected from the claimed group. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Qiu’s hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, or 1,4-butanediamine and Qiu’s p-phenylenediamine, m-phenylenediamine, 4, 4'-diaminodiphenyl ether, or 1,4-bis(4-aminophenoxy)benzene as Qiu’s diamine monomer, and to optimize a molar ratio of Qiu’s hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, or 1,4-butanediamine to Qiu’s p-phenylenediamine, m-phenylenediamine, 4, 4'-diaminodiphenyl ether, or 1,4-bis(4-aminophenoxy)benzene to be from 1:9 to 10:0. The proposed modification would read on wherein a molecular formula of the diamine containing a flexible long chain in main chain or side chain is shown as follows: H2N-X3-NH2, wherein X3 is an alkylene containing a long chain structure in main chain, and the aromatic diamine is selected from m-phenylenediamine 4,4’-diaminodiphenyl ether, p-phenylenediamine, and 1,4-bis(4-aminophenoxy)benzene as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying mechanical properties of Qiu’s benzoxazine-terminated imide and for optimizing the mechanical properties of Qiu’s benzoxazine-terminated imide because Qiu teaches that the diamine monomer is one of hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, 1,4-butanediamine, p-phenylenediamine, m-phenylenediamine, 4, 4'-diaminodiphenyl ether, or 1,4-bis(4-aminophenoxy)benzene (translation p. 5, l. 4-10), that the diamine monomer can also be hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, 1,4-butanediamine, p-phenylenediamine, m-phenylenediamine, 4,4'-diaminodiphenyl ether, or more than one (translation p. 10, l. 14-20), that the benzoxazine-terminated imide is obtained by reacting diamine-terminated imide as amine source with monohydric phenol and paraformaldehyde (translation p. 4, l. 23-24), that the diamine-terminated imide is obtained by thermal cyclization of small molecular polyamic acid in an inert gas (translation p. 4, l. 25-26), and that the small molecular polyamic acid is prepared by condensation reaction of dianhydride monomer and diamine monomer (translation p. 4, l. 27-28), which means that Qiu’s benzoxazine-terminated imide would comprise flexible segments due to the presence of Qiu’s hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, or 1,4-butanediamine because they are aliphatic diamines, that Qiu’s benzoxazine-terminated imide would further comprise rigid segments due to the presence of Qiu’s p-phenylenediamine, m-phenylenediamine, 4, 4'-diaminodiphenyl ether, or 1,4-bis(4-aminophenoxy)benzene because they are aromatic diamines, and that the presence of flexible segments and rigid segments would provide flexibility and strength to Qiu’s benzoxazine-terminated imide, which means that a molar ratio of Qiu’s hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, or 1,4-butanediamine to Qiu’s p-phenylenediamine, m-phenylenediamine, 4, 4'-diaminodiphenyl ether, or 1,4-bis(4-aminophenoxy)benzene would have affected the mechanical properties of Qiu’s benzoxazine-terminated imide.
Regarding claim 9, Qiu teaches that the diamine monomer is one of hexamethylenediamine, p-phenylenediamine, m-phenylenediamine, 4, 4'-diaminodiphenyl ether, or 1,4-bis(4-aminophenoxy)benzene (translation p. 5, l. 4-10), and that the diamine monomer can also be hexamethylenediamine, p-phenylenediamine, m-phenylenediamine, 4,4'-diaminodiphenyl ether, or more than one (translation p. 10, l. 14-20), which suggests selecting Qiu’s hexamethylenediamine and Qiu’s p-phenylenediamine, m-phenylenediamine, 4, 4'-diaminodiphenyl ether, or 1,4-bis(4-aminophenoxy)benzene as Qiu’s diamine monomer, which suggests wherein X3 is an alkylene containing 6 carbon atoms as claimed.
Qiu does not teach a specific embodiment wherein X3 is an alkylene or/and alkylene oxide containing 5-30 carbon atoms. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Qiu’s hexamethylenediamine and Qiu’s p-phenylenediamine, m-phenylenediamine, 4, 4'-diaminodiphenyl ether, or 1,4-bis(4-aminophenoxy)benzene as Qiu’s diamine monomer, and to optimize a molar ratio of Qiu’s hexamethylenediamine to Qiu’s p-phenylenediamine, m-phenylenediamine, 4, 4'-diaminodiphenyl ether, or 1,4-bis(4-aminophenoxy)benzene to be from 1:9 to 10:0. The proposed modification would read on wherein X3 is an alkylene containing 6 carbon atoms as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying mechanical properties of Qiu’s benzoxazine-terminated imide and for optimizing the mechanical properties of Qiu’s benzoxazine-terminated imide because Qiu teaches that the diamine monomer is one of hexamethylenediamine, p-phenylenediamine, m-phenylenediamine, 4, 4'-diaminodiphenyl ether, or 1,4-bis(4-aminophenoxy)benzene (translation p. 5, l. 4-10), that the diamine monomer can also be hexamethylenediamine, p-phenylenediamine, m-phenylenediamine, 4,4'-diaminodiphenyl ether, or more than one (translation p. 10, l. 14-20), that the benzoxazine-terminated imide is obtained by reacting diamine-terminated imide as amine source with monohydric phenol and paraformaldehyde (translation p. 4, l. 23-24), that the diamine-terminated imide is obtained by thermal cyclization of small molecular polyamic acid in an inert gas (translation p. 4, l. 25-26), and that the small molecular polyamic acid is prepared by condensation reaction of dianhydride monomer and diamine monomer (translation p. 4, l. 27-28), which means that Qiu’s benzoxazine-terminated imide would comprise flexible segments due to the presence of Qiu’s hexamethylenediamine because it is an aliphatic diamine, that Qiu’s benzoxazine-terminated imide would further comprise rigid segments due to the presence of Qiu’s p-phenylenediamine, m-phenylenediamine, 4, 4'-diaminodiphenyl ether, or 1,4-bis(4-aminophenoxy)benzene because they are aromatic diamines, and that the presence of flexible segments and rigid segments would provide flexibility and strength to Qiu’s benzoxazine-terminated imide, which means that a molar ratio of Qiu’s hexamethylenediamine to Qiu’s p-phenylenediamine, m-phenylenediamine, 4, 4'-diaminodiphenyl ether, or 1,4-bis(4-aminophenoxy)benzene would have affected the mechanical properties of Qiu’s benzoxazine-terminated imide.
Regarding claim 10, the limitation “the resin composition of claim 8, wherein the primary amine-capped flexible polyimide oligomer is prepared through steps of: (S1) dissolving the flexible diamine in a solvent under the protection of nitrogen to obtain a first mixture; (S2) stepwise adding the tetracarboxylic acid dianhydride to the first mixture; performing reaction at a first preset temperature for a first preset time to obtain a second mixture; and (S3) adding a catalyst or a water-carrying agent to the second mixture followed by reaction at a second preset temperature for a second preset time and precipitation or drying to obtain the primary amine-capped flexible polyimide oligomer” is a product-by-process limitation. The product is the resin composition of claim 8, and the process is the primary amine-capped flexible polyimide oligomer is prepared through steps of (S1), (S2), and (S3). Since Qiu in view of Takano renders obvious the resin composition of claim 8 as explained above, and since Qiu teaches that the benzoxazine-terminated imide is obtained by reacting diamine-terminated imide as amine source with monohydric phenol and paraformaldehyde (translation p. 4, l. 23-24), that the diamine-terminated imide is obtained by thermal cyclization of small molecular polyamic acid in an inert gas (translation p. 4, l. 25-26), and that the small molecular polyamic acid is prepared by condensation reaction of dianhydride monomer and diamine monomer (translation p. 4, l. 27-28), Qiu in view of Takano renders obvious the product of the product-by-process limitation. "[E]ven though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process (MPEP 2113)."
Regarding claim 11, Qiu teaches that the benzoxazine-terminated imide is obtained by reacting diamine-terminated imide as amine source with monohydric phenol and paraformaldehyde (translation p. 4, l. 23-24), which reads on wherein the aldehyde is paraformaldehyde as claimed.
Regarding claim 12, Qiu teaches that the benzoxazine-terminated imide is obtained by reacting diamine-terminated imide as amine source with monohydric phenol and paraformaldehyde (translation p. 4, l. 23-24), and that the monohydric phenol (translation p. 4, l. 24) is phenol (translation p. 6, l. 34; p. 7, l. 12, 30; p. 8, l. 4; p. 9, l. 16, 30), which reads on wherein the monofunctional phenolic compound is selected from phenol as claimed.
Regarding claim 13, Qiu does not teach that the epoxy resin is selected from the claimed group. However, Takano teaches a cyanate ester compound (p. 4, l. 11) having two, three, four cyanate groups (p. 8, l. 5-p. 9, l. 1), a maleimide compound (p. 4, l. 12) having two maleimide groups (p. 9, l. 38-42), and an epoxy resin (p. 4, l. 34) that is bisphenol A type epoxy resin, bisphenol E type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenol novolak type epoxy resin, bisphenol A novolak type epoxy resin, aralkyl novolac type epoxy resin, biphenyl aralkyl type epoxy resin, naphthylene ether type epoxy resin, cresol novolac type epoxy resin, polyfunctional phenol type epoxy resin, naphthalene type epoxy resin, anthracene type epoxy resin, naphthalene skeleton modified novolak type epoxy resin, phenol aralkyl type epoxy resin, naphthol aralkyl type epoxy resin, biphenyl type epoxy resin, or alicyclic type carboxy resin (p. 11, l. 11-20) that are present in a resin composition further comprising a benzoxazine compound (p, 4, l. 11), wherein the content of the benzoxazine compound in the resin composition is 1 to 25 parts by mass with respect to 100 parts by mass of the resin solid content (p. 4, l. 27-28; p. 6, l. 5-6), the content of the cyanate ester compound in the resin composition is 1 to 90 parts by mass with respect to 100 parts by mass of the resin solid content (p. 9, l. 32-35), and the content of the maleimide compound in the resin composition is 1 to 90 parts by mass with respect to 100 parts by mass of the resin solid content (p. 10, l. 7-10), which means that the content of the cyanate ester compound is from 1 / 25 * 100% = 4% to 90 / 1 * 100% = 9000% by weight of the benzoxazine, that the content of the maleimide compound is from 1 / 25 * 100% = 4% to 90 / 1 * 100% = 9000% by weight of the benzoxazine, and that the content of the epoxy resin is greater than 0% by weight of the benzoxazine. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to combine Takano’s cyanate ester compound having two, three, four cyanate groups, maleimide compound having two maleimide groups, and/or epoxy resin that is bisphenol A type epoxy resin, bisphenol E type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenol novolak type epoxy resin, bisphenol A novolak type epoxy resin, aralkyl novolac type epoxy resin, biphenyl aralkyl type epoxy resin, naphthylene ether type epoxy resin, cresol novolac type epoxy resin, polyfunctional phenol type epoxy resin, naphthalene type epoxy resin, anthracene type epoxy resin, naphthalene skeleton modified novolak type epoxy resin, phenol aralkyl type epoxy resin, naphthol aralkyl type epoxy resin, biphenyl type epoxy resin, or alicyclic type carboxy resin with Qiu’s benzoxazine-terminated imide, and to optimize the total content of Takano’s cyanate ester compound, maleimide compound, and/or epoxy resin to be from 4 to 50 parts by mass with respect to 100 parts by mass of Qiu’s benzoxazine-terminated imide. The proposed modification would read on wherein the epoxy resin is selected from phenolic epoxy resin, bisphenol A epoxy resin, bisphenol F epoxy resin, bisphenol S epoxy resin, and alicyclic epoxy resin as claimed. One of ordinary skill in the art would have been motivated to do so because Takano teaches that the cyanate ester compound (p. 4, l. 11) having two, three, four cyanate groups (p. 8, l. 5-p. 9, l. 1) is beneficial for providing a cured resin product with excellent characteristics such as glass transition temperature, low thermal expansion property, and plating adhesion (p. 9, l. 30-31), that the cyanate ester compound is beneficial for being useful at a content that is 1 to 90 parts by mass with respect to 100 parts by mass of the resin solid content in a resin composition (p. 9, l. 32-35), that the maleimide compound (p. 4, l. 12) having two maleimide groups (p. 9, l. 38-42) is beneficial for being useful at a content in the range of 1 to 90 parts by mass with respect to 100 parts by mass of the resin solid content in a resin composition (p. 10, l. 7-10), that this content is beneficial for providing a resin composition that is excellent in glass transition temperature (p. 10, l. 10-11), that the epoxy resin (p. 4, l. 34) that is bisphenol A type epoxy resin, bisphenol E type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenol novolak type epoxy resin, bisphenol A novolak type epoxy resin, aralkyl novolac type epoxy resin, biphenyl aralkyl type epoxy resin, naphthylene ether type epoxy resin, cresol novolac type epoxy resin, polyfunctional phenol type epoxy resin, naphthalene type epoxy resin, anthracene type epoxy resin, naphthalene skeleton modified novolak type epoxy resin, phenol aralkyl type epoxy resin, naphthol aralkyl type epoxy resin, biphenyl type epoxy resin, or alicyclic type carboxy resin (p. 11, l. 11-20) is beneficial for providing flame retardancy and heat resistance (p. 11, l. 24-25), and that they are beneficial for being useful in a resin composition further comprising a benzoxazine compound (p, 4, l. 11) at a content that is 1 to 25 parts by mass with respect to 100 parts by mass of the resin solid content in the resin composition (p. 4, l. 27-28; p. 6, l. 5-6), which would have been desirable for Qiu’s invention because Qiu teaches a benzoxazine-terminated imide (translation p. 4, l. 23-24), that it has a glass transition temperature (p. 5, l. 35-36; p. 7, l. 24-26; p. 8, l. 16-18; p. 9, l. 10-12; p. 10, l. 5-7), that it has flame retardancy (p. 4, l. 19-21; p. 5, l. 35-p. 6, l. 2; p. 7, l. 24-26; p. 8, l. 16-18; p. 9, l. 10-12; p. 10, l. 5-7), and that cured polybenzoxazine has heat resistance (p. 3, l. 27-28), which means that the total content of Takano’s cyanate ester compound, maleimide compound, and/or epoxy resin in parts by mass with respect to 100 parts by mass of Qiu’s benzoxazine-terminated imide would have affected glass transition temperature, flame retardancy, and/or heat resistance of the resulting composition, which means that optimizing the total content of Takano’s cyanate ester compound, maleimide compound, and/or epoxy resin in parts by mass with respect to 100 parts by mass of Qiu’s benzoxazine-terminated imide would have been beneficial for optimizing glass transition temperature, flame retardancy, and/or heat resistance of the resulting composition.
Regarding claim 14, Qiu does not teach that the maleimide resin is selected from the claimed group. However, Takano teaches a cyanate ester compound (p. 4, l. 11) having two, three, four cyanate groups (p. 8, l. 5-p. 9, l. 1), a maleimide compound (p. 4, l. 12) that is 4,4-diphenylmethane bismaleimide, m-phenylene bismaleimide, or 4,4-diphenyl ether bismaleimide (p. 9, l. 36-41), and an epoxy resin (p. 4, l. 34) having two or more epoxy groups (p. 11, l. 11-12), that are present in a resin composition further comprising a benzoxazine compound (p, 4, l. 11), wherein the content of the benzoxazine compound in the resin composition is 1 to 25 parts by mass with respect to 100 parts by mass of the resin solid content (p. 4, l. 27-28; p. 6, l. 5-6), the content of the cyanate ester compound in the resin composition is 1 to 90 parts by mass with respect to 100 parts by mass of the resin solid content (p. 9, l. 32-35), and the content of the maleimide compound in the resin composition is 1 to 90 parts by mass with respect to 100 parts by mass of the resin solid content (p. 10, l. 7-10), which means that the content of the cyanate ester compound is from 1 / 25 * 100% = 4% to 90 / 1 * 100% = 9000% by weight of the benzoxazine, that the content of the maleimide compound is from 1 / 25 * 100% = 4% to 90 / 1 * 100% = 9000% by weight of the benzoxazine, and that the content of the epoxy resin is greater than 0% by weight of the benzoxazine. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to combine Takano’s cyanate ester compound having two, three, four cyanate groups, maleimide compound that is 4,4-diphenylmethane bismaleimide, m-phenylene bismaleimide, or 4,4-diphenyl ether bismaleimide, and/or epoxy resin having two or more epoxy groups with Qiu’s benzoxazine-terminated imide, and to optimize the total content of Takano’s cyanate ester compound, maleimide compound, and/or epoxy resin to be from 4 to 50 parts by mass with respect to 100 parts by mass of Qiu’s benzoxazine-terminated imide. The proposed modification would read on wherein the maleimide resin is selected from m-phenylene bismaleimide resin, 4,4-diphenylmethane bismaleimide resin, and 4,4-diphenyl ether bismaleimide resin as claimed. One of ordinary skill in the art would have been motivated to do so because Takano teaches that the cyanate ester compound (p. 4, l. 11) having two, three, four cyanate groups (p. 8, l. 5-p. 9, l. 1) is beneficial for providing a cured resin product with excellent characteristics such as glass transition temperature, low thermal expansion property, and plating adhesion (p. 9, l. 30-31), that the cyanate ester compound is beneficial for being useful at a content that is 1 to 90 parts by mass with respect to 100 parts by mass of the resin solid content in a resin composition (p. 9, l. 32-35), that the maleimide compound (p. 4, l. 12) that is 4,4-diphenylmethane bismaleimide, m-phenylene bismaleimide, or 4,4-diphenyl ether bismaleimide (p. 9, l. 36-41) is beneficial for being useful at a content in the range of 1 to 90 parts by mass with respect to 100 parts by mass of the resin solid content in a resin composition (p. 10, l. 7-10), that this content is beneficial for providing a resin composition that is excellent in glass transition temperature (p. 10, l. 10-11), that the epoxy resin (p. 4, l. 34) having two or more epoxy groups (p. 11, l. 11-12) is beneficial for providing flame retardancy and heat resistance (p. 11, l. 24-25), and that they are beneficial for being useful in a resin composition further comprising a benzoxazine compound (p, 4, l. 11) at a content that is 1 to 25 parts by mass with respect to 100 parts by mass of the resin solid content in the resin composition (p. 4, l. 27-28; p. 6, l. 5-6), which would have been desirable for Qiu’s invention because Qiu teaches a benzoxazine-terminated imide (translation p. 4, l. 23-24), that it has a glass transition temperature (p. 5, l. 35-36; p. 7, l. 24-26; p. 8, l. 16-18; p. 9, l. 10-12; p. 10, l. 5-7), that it has flame retardancy (p. 4, l. 19-21; p. 5, l. 35-p. 6, l. 2; p. 7, l. 24-26; p. 8, l. 16-18; p. 9, l. 10-12; p. 10, l. 5-7), and that cured polybenzoxazine has heat resistance (p. 3, l. 27-28), which means that the total content of Takano’s cyanate ester compound, maleimide compound, and/or epoxy resin in parts by mass with respect to 100 parts by mass of Qiu’s benzoxazine-terminated imide would have affected glass transition temperature, flame retardancy, and/or heat resistance of the resulting composition, which means that optimizing the total content of Takano’s cyanate ester compound, maleimide compound, and/or epoxy resin in parts by mass with respect to 100 parts by mass of Qiu’s benzoxazine-terminated imide would have been beneficial for optimizing glass transition temperature, flame retardancy, and/or heat resistance of the resulting composition.
Regarding claim 15, Qiu does not teach that the cyanate ester resin is selected from the claimed group. However, Takano teaches a cyanate ester compound (p. 4, l. 11) that is 4,4’-dicyanodiphenylmethane, bis(4-cyanatophenyl) ethane, or 2,2-bis(4-cyanatophenyl) propane (p. 8, l. 11-12), a maleimide compound (p. 4, l. 12) having two maleimide groups (p. 9, l. 38-42), and an epoxy resin (p. 4, l. 34) having two or more epoxy groups (p. 11, l. 11-12), that are present in a resin composition further comprising a benzoxazine compound (p, 4, l. 11), wherein the content of the benzoxazine compound in the resin composition is 1 to 25 parts by mass with respect to 100 parts by mass of the resin solid content (p. 4, l. 27-28; p. 6, l. 5-6), the content of the cyanate ester compound in the resin composition is 1 to 90 parts by mass with respect to 100 parts by mass of the resin solid content (p. 9, l. 32-35), and the content of the maleimide compound in the resin composition is 1 to 90 parts by mass with respect to 100 parts by mass of the resin solid content (p. 10, l. 7-10), which means that the content of the cyanate ester compound is from 1 / 25 * 100% = 4% to 90 / 1 * 100% = 9000% by weight of the benzoxazine, that the content of the maleimide compound is from 1 / 25 * 100% = 4% to 90 / 1 * 100% = 9000% by weight of the benzoxazine, and that the content of the epoxy resin is greater than 0% by weight of the benzoxazine. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to combine Takano’s cyanate ester compound that is 4,4’-dicyanodiphenylmethane, bis(4-cyanatophenyl) ethane, or 2,2-bis(4-cyanatophenyl) propane, maleimide compound having two maleimide groups, and/or epoxy resin having two or more epoxy groups with Qiu’s benzoxazine-terminated imide, and to optimize the total content of Takano’s cyanate ester compound, maleimide compound, and/or epoxy resin to be from 4 to 50 parts by mass with respect to 100 parts by mass of Qiu’s benzoxazine-terminated imide. The proposed modification would read on wherein the cyanate ester resin is selected from bisphenol A cyanate ester resin, bisphenol E cyanate ester resin, and bisphenol F cyanate ester resin as claimed. One of ordinary skill in the art would have been motivated to do so because Takano teaches that the cyanate ester compound (p. 4, l. 11) that is 4,4’-dicyanodiphenylmethane, bis(4-cyanatophenyl) ethane, or 2,2-bis(4-cyanatophenyl) propane (p. 8, l. 11-12) is beneficial for providing a cured resin product with excellent characteristics such as glass transition temperature, low thermal expansion property, and plating adhesion (p. 9, l. 30-31), that the cyanate ester compound is beneficial for being useful at a content that is 1 to 90 parts by mass with respect to 100 parts by mass of the resin solid content in a resin composition (p. 9, l. 32-35), that the maleimide compound (p. 4, l. 12) having two maleimide groups (p. 9, l. 38-42) is beneficial for being useful at a content in the range of 1 to 90 parts by mass with respect to 100 parts by mass of the resin solid content in a resin composition (p. 10, l. 7-10), that this content is beneficial for providing a resin composition that is excellent in glass transition temperature (p. 10, l. 10-11), that the epoxy resin (p. 4, l. 34) having two or more epoxy groups (p. 11, l. 11-12) is beneficial for providing flame retardancy and heat resistance (p. 11, l. 24-25), and that they are beneficial for being useful in a resin composition further comprising a benzoxazine compound (p, 4, l. 11) at a content that is 1 to 25 parts by mass with respect to 100 parts by mass of the resin solid content in the resin composition (p. 4, l. 27-28; p. 6, l. 5-6), which would have been desirable for Qiu’s invention because Qiu teaches a benzoxazine-terminated imide (translation p. 4, l. 23-24), that it has a glass transition temperature (p. 5, l. 35-36; p. 7, l. 24-26; p. 8, l. 16-18; p. 9, l. 10-12; p. 10, l. 5-7), that it has flame retardancy (p. 4, l. 19-21; p. 5, l. 35-p. 6, l. 2; p. 7, l. 24-26; p. 8, l. 16-18; p. 9, l. 10-12; p. 10, l. 5-7), and that cured polybenzoxazine has heat resistance (p. 3, l. 27-28), which means that the total content of Takano’s cyanate ester compound, maleimide compound, and/or epoxy resin in parts by mass with respect to 100 parts by mass of Qiu’s benzoxazine-terminated imide would have affected glass transition temperature, flame retardancy, and/or heat resistance of the resulting composition, which means that optimizing the total content of Takano’s cyanate ester compound, maleimide compound, and/or epoxy resin in parts by mass with respect to 100 parts by mass of Qiu’s benzoxazine-terminated imide would have been beneficial for optimizing glass transition temperature, flame retardancy, and/or heat resistance of the resulting composition.
Regarding claim 16, Qiu does not an adhesive, comprising; the resin composition of claim 1, and a curing accelerator. However, Takano teaches a curing accelerator that is present in a resin composition (p. 12, l. 23) further comprising a benzoxazine compound (p, 4, l. 11). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to combine Takano’s curing accelerator with Qiu’s benzoxazine-terminated imide. The proposed modification would read on an adhesive, comprising; the resin composition of claim 1, and a curing accelerator as claimed. One of ordinary skill in the art would have been motivated to do so because Takano teaches that the curing accelerator is beneficial for appropriately adjusting a curing rate in a resin composition (p. 12, l. 23-24) further comprising a benzoxazine compound (p, 4, l. 11), a cyanate ester compound (p. 4, l. 11) having two, three, four cyanate groups (p. 8, l. 5-p. 9, l. 1), a maleimide compound (p. 4, l. 12) having two maleimide groups (p. 9, l. 38-42), and an epoxy resin (p. 4, l. 34) having two or more epoxy groups (p. 11, l. 11-12), which would have been desirable for Qiu’s invention because Qiu teaches a benzoxazine-terminated imide (translation p. 4, l. 23-24), and that polybenzoxazine can be cured (translation p. 3, l. 27-28), and which would have been beneficial for adjusting the curing rate of Takano’s cyanate ester compound having two, three, four cyanate groups, maleimide compound having two maleimide groups, and/or epoxy resin having two or more epoxy groups.
Qiu does not teach that the adhesive further comprises an organic solvent. However, Takano teaches an organic solvent that is present in a resin composition (p. 13, l. 12) further comprising a benzoxazine compound (p, 4, l. 11). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to combine Takano’s organic solvent with Qiu’s benzoxazine-terminated imide. The proposed modification would read on the adhesive further comprising an organic solvent as claimed. One of ordinary skill in the art would have been motivated to do so because Takano teaches that the organic solvent is beneficial for being useful in a resin composition (p. 13, l. 12) further comprising a benzoxazine compound (p, 4, l. 11), a cyanate ester compound (p. 4, l. 11) having two, three, four cyanate groups (p. 8, l. 5-p. 9, l. 1), a maleimide compound (p. 4, l. 12) having two maleimide groups (p. 9, l. 38-42), and an epoxy resin (p. 4, l. 34) having two or more epoxy groups (p. 11, l. 11-12), which would have been desirable for Qiu’s invention because Qiu teaches a benzoxazine-terminated imide (translation p. 4, l. 23-24), and because Takano’s organic solvent would have been beneficial for reducing the viscosity of the resulting composition, which would have been beneficial for improving processability of the resulting composition.
Regarding claim 17, Qiu does not teach that the curing accelerator is selected from the claimed group. However, Takano teaches a curing accelerator (p. 12, l. 23) that is benzoyl peroxide (p. 12, l. 36-37) or azobisisobutyronitrile (p. 12, l. 38) that is present in a resin composition (p. 12, l. 23) further comprising a benzoxazine compound (p, 4, l. 11). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to combine Takano’s curing accelerator that is benzoyl peroxide or azobisisobutyronitrile with Qiu’s benzoxazine-terminated imide. The proposed modification would read on wherein the curing accelerator is selected from azobisisobutyronitrile, and benzoyl peroxide as claimed. One of ordinary skill in the art would have been motivated to do so because Takano teaches that the curing accelerator (p. 12, l. 23) that is benzoyl peroxide (p. 12, l. 36-37) or azobisisobutyronitrile (p. 12, l. 38) is beneficial for appropriately adjusting a curing rate in a resin composition (p. 12, l. 23-24) further comprising a benzoxazine compound (p, 4, l. 11), a cyanate ester compound (p. 4, l. 11) having two, three, four cyanate groups (p. 8, l. 5-p. 9, l. 1), a maleimide compound (p. 4, l. 12) having two maleimide groups (p. 9, l. 38-42), and an epoxy resin (p. 4, l. 34) having two or more epoxy groups (p. 11, l. 11-12), which would have been desirable for Qiu’s invention because Qiu teaches a benzoxazine-terminated imide (translation p. 4, l. 23-24), and that polybenzoxazine can be cured (translation p. 3, l. 27-28), and which would have been beneficial for adjusting the curing rate of Takano’s cyanate ester compound having two, three, four cyanate groups, maleimide compound having two maleimide groups, and/or epoxy resin having two or more epoxy groups.
Regarding claim 18, Qiu does not teach that the organic solvent is selected from the claimed group. However, Takano teaches an organic solvent (p. 13, l. 12) that is acetone, methyl ethyl ketone, or dimethylacetamide (p. 13, l. 18-22) that is present in a resin composition (p. 13, l. 12) further comprising a benzoxazine compound (p, 4, l. 11). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to combine Takano’s organic solvent that is acetone, methyl ethyl ketone, or dimethylacetamide. The proposed modification would read on wherein the organic solvent is selected from acetone, butanone, and N,N-dimethylacetamide as claimed. One of ordinary skill in the art would have been motivated to do so because Takano teaches that the organic solvent (p. 13, l. 12) that is acetone, methyl ethyl ketone, or dimethylacetamide (p. 13, l. 18-22) is beneficial for being useful in a resin composition (p. 13, l. 12) further comprising a benzoxazine compound (p, 4, l. 11), a cyanate ester compound (p. 4, l. 11) having two, three, four cyanate groups (p. 8, l. 5-p. 9, l. 1), a maleimide compound (p. 4, l. 12) having two maleimide groups (p. 9, l. 38-42), and an epoxy resin (p. 4, l. 34) having two or more epoxy groups (p. 11, l. 11-12), which would have been desirable for Qiu’s invention because Qiu teaches a benzoxazine-terminated imide (translation p. 4, l. 23-24), and because Takano’s organic solvent would have been beneficial for reducing the viscosity of the resulting composition, which would have been beneficial for improving processability of the resulting composition.
Regarding claim 19, Qiu teaches a polybenzoxazine-terminated imide film prepared form he benzoxazine-terminated imide (translation p. 4, l. 19-20), and since Qiu in view of Takano renders obvious the adhesive of claim 16 as explained above, Qiu in view of Takano renders obvious wherein the adhesive can be used in film adhesive materials, adhesive layers, adhesive sheets, resin-coated copper foils, copper-clad laminates and multi-layer resin substrates comprising the adhesive of claim 16 as claimed.
Response to Arguments
Applicant’s arguments, see p. 5, filed 09/26/2025, with respect to the rejection of claims 1-4 and 6-19 under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, have been fully considered and are persuasive. The rejection of claims 1-4 and 6-19 under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, has been withdrawn.
Applicant's arguments filed 09/26/2025 have been fully considered but they are not persuasive. In response to the applicant’s argument that the benzoxazine-terminated imide of Qiu is obtained by reacting diamine-terminated imide with monohydric phenol and paraformaldehyde, not the primary amine-capped flexible polyimide oligomer in the application, and that Qiu does not disclose the primary amine-capped flexible polyimide oligomer (p. 6), Qiu’s diamine-terminated imide (translation p. 4, l. 23-24) that has the following structural formula: (translation p. 4, l. 33)
PNG
media_image5.png
156
560
media_image5.png
Greyscale
(untranslated [0016]) and that is obtained by thermal cyclization of small molecular polyamic acid in an inert gas (translation p. 4, l. 25-26), wherein the small molecular polyamic acid is prepared by condensation reaction of dianhydride monomer and diamine monomer (translation p. 4, l. 27-28), wherein the diamine monomer is hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, or 1,4-butanediamine (translation p. 5, l. 4-5), reads on the primary amine-capped flexible polyimide oligomer as claimed.
In response to the applicant’s argument that Qiu does not disclose the resin mixture (p. 6), the rejection of the claims is not based on Qiu individually. The rejection of the claims is based on the combination of Qiu in view of Takano rendering it obvious that the resin composition further comprises a resin mixture, wherein the resin mixture comprises one or more of an epoxy resin, a maleimide resin, and a cyanate ester resin containing two or more functional groups, and the resin mixture is 4%-50% by weight of the benzoxazine as claimed. One cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).
In response to the applicant’s argument that Qiu does not disclose the ratio between the resin mixture and the benzoxazine (p. 6), the rejection of the claims is not based on Qiu individually. The rejection is based on the combination of Qiu in view of Takano rendering it obvious that the resin mixture is 4%-50% by weight of the benzoxazine as claimed. One cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).
In response to the applicant’s argument that Qiu does not disclose that the primary amine-capped flexible polyimide oligomer is a reaction product of a tetracarboxylic acid dianhydride and a flexible diamine and that the molar ratio of dianhydride in the tetracarboxylic acid dianhydride to the flexible diamine is 1:(1.01-1.1) (p. 6), Qiu teaches that the diamine-terminated imide is obtained by thermal cyclization of small molecular polyamic acid in an inert gas (translation p. 4, l. 25-26), wherein the small molecular polyamic acid is prepared by condensation reaction of dianhydride monomer and diamine monomer (translation p. 4, l. 27-28), wherein the diamine-terminated imide has the following structural formula: (translation p. 4, l. 33)
PNG
media_image5.png
156
560
media_image5.png
Greyscale
(untranslated [0016]), wherein the diamine monomer is hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, or 1,4-butanediamine (translation p. 5, l. 4-5), wherein the molar ratio of the amine monomer to the dianhydride monomer is 1:1 to 2:1 (p. 5, l. 20-21), which reads on the primary amine-capped flexible polyimide oligomer is a reaction product of a tetracarboxylic acid dianhydride and a flexible diamine, and a molar ratio of dianhydride in the tetracarboxylic acid dianhydride to the flexible diamine is 1:(1-2). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize Qiu’s molar ratio of Qiu’s amine monomer to Qiu’s dianhydride monomer to be 1.01:1 to 1.1:1. The proposed modification would read on wherein a molar ratio of dianhydride in the tetracarboxylic acid dianhydride to the flexible diamine is 1:(1.01-1.1) as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for optimizing a yield of Qiu’s diamine-terminated imide from Qiu’s dianhydride monomer and Qiu’s diamine monomer because Qiu teaches that a molar ratio of dianhydride in the tetracarboxylic acid dianhydride to the flexible diamine is 1:(1-2), that the small molecular polyamic acid is prepared by condensation reaction of dianhydride monomer and diamine monomer (translation p. 4, l. 27-28), and that the diamine-terminated imide is obtained by thermal cyclization of small molecular polyamic acid in an inert gas (translation p. 4, l. 25-26), which means that Qiu’s molar ratio of Qiu’s amine monomer to Qiu’s dianhydride monomer would have affected a yield of Qiu’s diamine-terminated imide from Qiu’s dianhydride monomer and Qiu’s diamine monomer.
In response to the applicant’s argument that Takano does not disclose that the benzoxazine compound is primary amine-capped (p. 6), it is noted that “the benzoxazine compound is primary amine-capped” is not recited in the rejected claim(s). Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993). Claim 1 recites that “the benzoxazine is synthesized from a primary amine-capped flexible polyimide oligomer, an aldehyde and a monofunctional phenolic compound” in lines 4-5. Regarding this limitation, the rejection is based on Qiu’s teaching of a benzoxazine-terminated imide that is obtained by reacting diamine-terminated imide as amine source with monohydric phenol and paraformaldehyde (translation p. 4, l. 23-24), wherein the benzoxazine end-capped imide has the following structure: (translation p. 4, l. 29)
PNG
media_image1.png
150
632
media_image1.png
Greyscale
(untranslated [0012]), wherein n=1~5 (translation p. 4, l. 30),
PNG
media_image2.png
100
94
media_image2.png
Greyscale
(untranslated [0014]) represents a residual group derived from a dianhydride monomer (translation p. 4, l. 31),
PNG
media_image3.png
92
100
media_image3.png
Greyscale
(untranslated [0014]) represents a residual group derived from a diamine monomer (translation p. 4, l. 32-33), and
PNG
media_image4.png
92
102
media_image4.png
Greyscale
(untranslated [0014]) represents a residual group derived from a monohydric phenol (translation p. 4, l. 32), wherein the diamine-terminated imide is obtained by thermal cyclization of small molecular polyamic acid in an inert gas (translation p. 4, l. 25-26), wherein the small molecular polyamic acid is prepared by condensation reaction of dianhydride monomer and diamine monomer (translation p. 4, l. 27-28), wherein the diamine-terminated imide has the following structural formula: (translation p. 4, l. 33)
PNG
media_image5.png
156
560
media_image5.png
Greyscale
(untranslated [0016]), wherein the diamine monomer is hexamethylenediamine, 1,2-propanediamine, 1,3-propanediamine, or 1,4-butanediamine (translation p. 5, l. 4-5), which reads on the benzoxazine is synthesized from a primary amine-capped flexible polyimide oligomer, an aldehyde, and a monofunctional phenolic compound as claimed. Regarding Takano, the rejection only relies on Takano to the extent that the combination of Qiu in view of Takano renders it obvious that the resin composition further comprising a resin mixture, wherein the resin mixture comprises one or more of an epoxy resin, a maleimide resin, and a cyanate ester resin containing two or more functional groups, and the resin mixture is 4%-50% by weight of the benzoxazine as claimed. One cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).
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.
Correspondence
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DAVID KARST whose telephone number is (571)270-7732. The examiner can normally be reached Monday-Friday 8:00 AM-5:00 PM.
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, Mark Eashoo can be reached at 571-272-1197. 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.
/DAVID T KARST/Primary Examiner, Art Unit 1767
Prosecution Insights