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 .
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.
Acknowledgment is made of applicant’s claim for foreign priority under 35 U.S.C. 119 (a)-(d). The certified copy has been filed in parent Application No. 17/550,439, filed on 12/14/2021.
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 1-10 are rejected under 35 U.S.C. 103 as being unpatentable over Mizori et al. (US 2011/0130485 A1) in view of Domeier (US 4,654,407).
Regarding claims 1-3 and 7, Mizori teaches adhesive compositions including bismaleimide compounds and at least one curing initiator [0014], wherein the bismaleimide compounds are imide-extended bismaleimide compounds having the structure
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, wherein each of R and Q is independently a substituted or an unsubstituted aromatic moiety, R2 is H, and n is an integer having the value between 1 and about 10 [0009], wherein the imide-extended bismaleimide compound is produced by contacting a dianhydride with a diamine under conditions suitable to form an imide having terminal amino moieties, and contacting the terminal amino moieties with maleic anhydride under conditions suitable to form a maleimide, thereby producing an imide-extended bismaleimide monomer [0020], wherein a wide variety of diamines are contemplated for use, such as for example, bis(4-amino-3,5-dimethylphenyl)methane, bis(4-amino-3,5-diethylphenyl)methane, bis(4-amino-3-methylphenyl)methane, bis(4-amino-3-ethylphenyl)methane, 2,2-bis(4,-(4aminophenoxy)phenyl)sulfone, 4,4'-oxydianiline, 4,4'-diaminodiphenyl sulfide, or 2,2-bis(4-(4-aminophenoxy)phenyl)propane [0137], wherein a wide variety of anhydrides are contemplated for use, such as, for example, 4,4'-bisphenol A diphthalic anhydride [0140], wherein the curing initiator is a free-radical initiator [0161], wherein the free radical initiator is any chemical species which, upon exposure to sufficient energy, e.g., heat, decomposes into two parts with are uncharged, but which each possess at least one unpair electron [0161], which reads on a heat-curable maleimide resin composition comprising (A) a maleimide resin optionally represented by the formula (3) and having a number average molecular weight of not lower than 1,729.72, and (C) a reaction initiator, wherein X1 independently represents a divalent group, k is a number of 1 to 10, l is a number of 1 to 9, each of A1 and A2 independently represents a divalent aromatic group, the divalent group represented by X1 being selected from the following formulae,
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, and the divalent aromatic group represented by A1 and A2 being expressed by the formula (4) or (5) wherein X1 is as defined in the formula (3), wherein X1 independently represents a divalent group, the divalent group represented by X1 being selected from the following formulae,
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, R2 independently represents a hydrogen atom, or an unsubstituted aliphatic hydrocarbon group having 1 to 2 carbon atoms, X2 independently represents a divalent group selected from the following formulae,
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wherein a is a number of 1, wherein the reaction initiator as the component (C) is a radical polymerization initiator, and an adhesive agent comprised of the heat-curable maleimide resin composition according to claim 1. The number average molecular weight is based on the calculation 12.011 g/mol * (4 + 12 + (31 + 12) * 1 + 31 + 12 + 4) + 1.00784 g/mol * (2 + 8 + (20 + 8) * 1 + 20 + 8 + 2) + 14.0067 g/mol * (1 + (2) * 1 + 2 + 1) + 15.999 g/mol * (2 + 1 + (6 + 1) * 1 + 6 + 1 + 2) + 32.065 g/mol * 0 = 1,729.72 g/mol. Mizori teaches that in other embodiments, there is at least one co-monomer typically present in the composition, and that such comonomers include, for example, allyl functional compounds [0160], which optionally reads on the heat-curable maleimide resin composition further comprising (B) an organic compound having, in one molecule, at least one ally group.
Mizori does not teach a specific embodiment wherein the maleimide resin is represented by the formula (3) as claimed. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select at least one of Mizori’s bis(4-amino-3,5-dimethylphenyl)methane, bis(4-amino-3,5-diethylphenyl)methane, bis(4-amino-3-methylphenyl)methane, bis(4-amino-3-ethylphenyl)methane, 2,2-bis(4,-(4aminophenoxy)phenyl)sulfone, 4,4'-oxydianiline, 4,4'-diaminodiphenyl sulfide, and 2,2-bis(4-(4-aminophenoxy)phenyl)propane as Mizori’s diamine that is contacted with Mizori’s dianhydride to produce Mizori’s imide-extended bismaleimide compound, and to select Mizori’s 4,4'-bisphenol A diphthalic anhydride as Mizori’s dianhydride that is contacted with Mizori’s diamine to produce Mizori’s imide-extended bismaleimide compound. The proposed modification would read on the heat-curable maleimide resin composition comprising (A) a maleimide resin represented by the formula (3), wherein X1 independently represents a divalent group, k is a number of 1 to 10, l is a number of 1 to 9, each of A1 and A2 independently represents a divalent aromatic group, the divalent group represented by X1 being selected from the following formulae,
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, and the divalent aromatic group represented by A1and A2 being expressed by the formula (4) or (5) wherein X1 is as defined in the formula (3), wherein X1 independently represents a divalent group, the divalent group represented by X1 being selected from the following formulae,
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, R2 independently represents a hydrogen atom, or an unsubstituted aliphatic hydrocarbon group having 1 to 2 carbon atoms, X2 independently represents a divalent group selected from the following formulae,
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wherein a is a number of 1 as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for providing a species of diamine and a species of dianhydride that are suitable for producing Mizori’s imide-extended bismaleimide compound or because it would have been obvious to try with a reasonable expectation of success because Mizori teaches that the imide-extended bismaleimide compound is produced by contacting a dianhydride with a diamine under conditions suitable to form an imide having terminal amino moieties, and contacting the terminal amino moieties with maleic anhydride under conditions suitable to form a maleimide, thereby producing an imide-extended bismaleimide monomer [0020], that a wide variety of diamines are contemplated for use, such as for example, bis(4-amino-3,5-dimethylphenyl)methane, bis(4-amino-3,5-diethylphenyl)methane, bis(4-amino-3-methylphenyl)methane, bis(4-amino-3-ethylphenyl)methane, 2,2-bis(4,-(4aminophenoxy)phenyl)sulfone, 4,4'-oxydianiline, 4,4'-diaminodiphenyl sulfide, or 2,2-bis(4-(4-aminophenoxy)phenyl)propane [0137], and that a wide variety of anhydrides are contemplated for use, such as, for example, 4,4'-bisphenol A diphthalic anhydride [0140]. Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)).
Mizori does not teach with sufficient specificity wherein the maleimide resin has a number average molecular of not lower than 3,000. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Mizori’s n in Mizori’s structure
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to be an integer having the value from 4 to about 10. The proposed modification would read on the maleimide resin having a number average molecular weight of 3,099.118 or greater, wherein k is a number of 4 to 10, and l is a number of 3 to 10 as claimed. The number average molecular weight is based on the calculation 12.011 g/mol * (4 + 12 + (31 + 12) * 3 + 31 + 12 + 4) + 1.00784 g/mol * (2 + 8 + (20 + 8) * 3 + 20 + 8 + 2) + 14.0067 g/mol * (1 + (2) * 3 + 2 + 1) + 15.999 g/mol * (2 + 1 + (6 + 1) * 3 + 6 + 1 + 2) + 32.065 g/mol * 0 = 3,099.118 g/mol as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been obvious to try with a reasonable expectation of success because Mizori teaches that n is an integer having the value between 1 and about 10 [0009], which encompasses an integer having the value from 4 to about 10. Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)). In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists (MPEP 2144.05(I)).
Mizori does not teach that the heat-curable maleimide resin composition further comprises (B) an organic compound having, in one molecule, at least one allyl group and at least one isocyanuric ring, and that the organic compound as the component (B) has, in one molecule, two or more allyl groups. However, Domeier teaches triallyl isocyanurate (4:44-45) that is a liquid coreactant in a composition (4:38-39) and that is a comonomer characterized by the presence of -CH=CH2 groups which can polymerized or react with the maleimide groups of a bismaleimide (4:52-57), wherein additional components in the composition include initiators for vinyl polymerization such as di-t-butyl peroxide, dicumyl peroxide, 1,1-bis(t-butylperoxy)cylcohexane, t-butyl perbenzoate, and the like (12:4-8). Mizori and Domeier are analogous art because both references are in the same field of endeavor of a heat-curable maleimide resin composition comprising a maleimide resin, a reaction initiator, and optionally an organic compound having, in one molecule, at least one allyl group. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Domeier’s triallyl isocyanurate to modify Mizori’s adhesive compositions. The proposed modification would read on the heat-curable maleimide resin composition further comprising (B) an organic compound having, in one molecule, at least one allyl group and at least one isocyanuric ring as claimed, wherein the organic compound as the component (B) has, in one molecule, two or more allyl groups as claimed. One of ordinary skill in the art would have been motivated to do so because Domeier teaches that the triallyl isocyanurate (4:44-45) is beneficial for being a liquid coreactant (4:38-39) and a comonomer characterized by the presence of -CH=CH2 groups which can polymerized or react with the maleimide groups of a bismaleimide (4:52-57) in a composition that include initiators for vinyl polymerization such as di-t-butyl peroxide, dicumyl peroxide, 1,1-bis(t-butylperoxy)cylcohexane, t-butyl perbenzoate, and the like (12:4-8), wherein the composition may be used as matrix resins for adhesives (12:56-58), which would have been desirable for Mizori’s adhesive compositions because Mizori teaches that the adhesive compositions include bismaleimide compounds and at least one curing initiator [0014], and that in other embodiments, there is at least one co-monomer typically present in the composition, and that such comonomers include, for example, allyl functional compounds [0160].
Regarding claims 4 and 8, Mizori teaches that the adhesive is positioned onto a substrate [0178], that the adhesive composition is applied to a first article [0184], and that the imide-extended polymaleimides can be used to make thermally resistant film adhesives and can be used in the fabrication of anisotropic conductive adhesive films [0006], which reads on an uncured resin film comprised of the heat-curable maleimide resin composition according to claim 1 as claimed, and a substrate comprising the heat-curable maleimide resin composition according to claim 1 as claimed.
Regarding claim 5, Mizori teaches that the adhesive is positioned onto a substrate [0178], that once the adhesive is positioned onto the substrate, an electronic component is then contacted with the dispensed adhesive, and the adhesive is cured to bond the electronic component to the substrate [0178], that the adhesive composition is applied to a first article [0184], that the first article and a second article are brought into intimate contact to form an assembly [0185], and that the assembly is subjected to conditions suitable to cure the adhesive composition [0186], which reads on a cured resin film comprised of a cured product of the heat-curable maleimide resin composition according to claim 1 as claimed.
Regarding claim 6, Mizori does not teach a prepreg comprising the heat-curable maleimide resin composition according to claim 1, and a fiber base material. However, Domeier teaches preimpregnated reinforcement made by combining a component ii with a structural fiber (12:19-21), wherein the component ii is a prepregable resin composition comprising a bismaleimide and one or more liquid coreactants (2:14-31), wherein the liquid coreactant is (4:38-39) triallyl isocyanurate (4:44-45). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found obvious to combine Mizori’s adhesive compositions and Domeier’s triallyl isocyanurate with Domeier’s structural fiber, thereby making preimpregnated reinforcement, as suggested by Domeier. The proposed modification would read on a prepreg comprising the heat-curable maleimide resin composition according to claim 1, and a fiber base material as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for providing reinforcement for Mizori’s adhesive compositions, which would have been beneficial for modifying mechanical properties of Mizori’s adhesive compositions, and because it would have been beneficial for providing an additional utility for Mizori’s adhesive compositions because Domeier teaches preimpregnated reinforcement made by combining a component ii with a structural fiber (12:19-21), wherein the component ii is a prepregable resin composition comprising a bismaleimide and one or more liquid coreactants (2:14-31), wherein the liquid coreactant is (4:38-39) triallyl isocyanurate (4:44-45), and because Mizori teaches that the adhesive compositions include bismaleimide compounds [0014], which means that Domeier’s composition is substantially similar in composition to Mizori’s adhesive composition, which means that Mizori’s adhesive composition would have been useful for combining it with Domeier’s structural fiber. Also, one of ordinary skill in the art would have been motivated to do so because Domeier teaches that the triallyl isocyanurate (4:44-45) is beneficial for being a liquid coreactant (4:38-39) and a comonomer characterized by the presence of -CH=CH2 groups which can polymerized or react with the maleimide groups of a bismaleimide (4:52-57) in a composition that include initiators for vinyl polymerization such as di-t-butyl peroxide, dicumyl peroxide, 1,1-bis(t-butylperoxy)cylcohexane, t-butyl perbenzoate, and the like (12:4-8), wherein the composition may be used as matrix resins for adhesives (12:56-58), which would have been desirable for Mizori’s adhesive compositions because Mizori teaches that the adhesive compositions include bismaleimide compounds and at least one curing initiator [0014], and that in other embodiments, there is at least one co-monomer typically present in the composition, and that such comonomers include, for example, allyl functional compounds [0160].
Regarding claim 9, Mizori teaches that the maleimides will be present in the curable adhesive compositions in an amount from 0.05 to 98 weight percent (wt %) based on the organic components present [0147], that the imide-extended bismaleimide compound is present in the composition from 0.05 weight percent to about 98 weight percent (wt %) based on total weight of the composition [0160], that the at least one curing initiator is typically present in the composition from 0.1 wt % to about 5 wt % based on total weight of the composition [0161], that in other embodiments, there is at least one co-monomer typically present in the composition from 10 wt % to about 90 wt % based on total weight of the composition [0160], and that such comonomers include, for example, allyl functional compounds [0160], which reads on wherein said component (A) is contained in the composition in an amount of from 0.05 to 98% by mass, and said component (C) is contained in the composition in an amount of from 0.1 to 5 parts by mass of a sum total of the components (A) and (B). The parts by mass of said component (C) is based on the calculations 0.1 / (100 - 0.1) * 100 = 0.1 and 5 / (100 - 5) * 100 = 5.
Mizori does not teach with sufficient specificity that said component (A) is contained in the composition in an amount of from 20 to 90% by mass. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize the weight percent of Mizori’s imide-extended bismaleimide compound in Mizori’s adhesive composition to be from 20 to 90 weight percent based on total weight of Mizori’s adhesive composition. The proposed modification would read on wherein said component (A) is contained in the composition in an amount of from 20 to 90% by mass as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for optimizing toughness and thermal stability of Mizori’s adhesive composition and for optimizing an extent of curing of Mizori’s adhesive composition when it is cured because Mizori teaches that the maleimides will be present in the curable adhesive compositions in an amount from 0.05 to 98 weight percent (wt %) based on the organic components present [0147], that the imide-extended bismaleimide compound is present in the composition from 0.05 weight percent to about 98 weight percent (wt %) based on total weight of the composition [0160], that when incorporated into a thermoset composition, the imide-extended maleimide compounds reduce brittleness and increase toughness in the composition, while not sacrificing thermal stability [0008], that the imide functional group is one of the most thermally stable groups known [0008], that the imide-extended maleimide compounds may be added to available resins as a toughening agent [0147], that the bismaleimide monomer may be with other thermoset monomers to make a fully formulated adhesive [0158], and that curing can be completed by the application of heat to accomplish a free-radical cure [0172], which means that the weight percent of Mizori’s imide-extended bismaleimide compound in Mizori’s adhesive composition in weight percent based on total weight of Mizori’s adhesive composition would have affected toughness and thermal stability of Mizori’s adhesive composition, and would have affected an extent of curing of Mizori’s adhesive composition when it is cured.
Mizori does not teach that said component (B) is contained in an amount of from 3 to 50 parts by mass per 100 parts by mass of a sum total of the components (A) and (B). However, Domeier teaches triallyl isocyanurate (4:44-45) that is a liquid coreactant in a composition (4:38-39) and that is a comonomer characterized by the presence of -CH=CH2 groups which can polymerized or react with the maleimide groups of a bismaleimide (4:52-57), wherein additional components in the composition include initiators for vinyl polymerization such as di-t-butyl peroxide, dicumyl peroxide, 1,1-bis(t-butylperoxy)cylcohexane, t-butyl perbenzoate, and the like (12:4-8). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Domeier’s triallyl isocyanurate to modify Mizori’s adhesive compositions, and to optimize the weight percent of Domeier’s triallyl isocyanurate to be from 10 to 50 weight percent based on total weight of Mizori’s imide-extended bismaleimide compound and Domeier’s triallyl isocyanurate. The proposed modification would read on wherein said component (B) is contained in the composition in an amount of from 10 to 50 parts by mass per 100 parts by mass of a sum total of the components (A) and (B) as claimed. One of ordinary skill in the art would have been motivated to do so because Domeier teaches that the triallyl isocyanurate (4:44-45) is beneficial for being a liquid coreactant (4:38-39) and a comonomer characterized by the presence of -CH=CH2 groups which can polymerized or react with the maleimide groups of a bismaleimide (4:52-57) in a composition that include initiators for vinyl polymerization such as di-t-butyl peroxide, dicumyl peroxide, 1,1-bis(t-butylperoxy)cylcohexane, t-butyl perbenzoate, and the like (12:4-8), wherein the composition may be used as matrix resins for adhesives (12:56-58), which would have been desirable for Mizori’s adhesive compositions because Mizori teaches that the adhesive compositions include bismaleimide compounds and at least one curing initiator [0014], that in other embodiments, there is at least one co-monomer typically present in the composition from 10 wt % to about 90 wt % based on total weight of the composition, that such comonomers include, for example, allyl functional compounds [0160], that the imide-extended maleimide compounds may be added to available resins as a toughening agent [0147], that the bismaleimide monomer may be with other thermoset monomers to make a fully formulated adhesive [0158], and that curing can be completed by the application of heat to accomplish a free-radical cure [0172], which means that the weight percent of Domeier’s triallyl isocyanurate in weight percent based on total weight of Mizori’s imide-extended bismaleimide compound and Domeier’s triallyl isocyanurate would have affected an extent of curing of Mizori’s adhesive composition when it is cured, and would have affected toughness and thermal stability of Mizori’s adhesive composition, which means that optimizing the weight percent of Domeier’s triallyl isocyanurate in weight percent based on total weight of Mizori’s imide-extended bismaleimide compound and Domeier’s triallyl isocyanurate would have been beneficial for optimizing an extent of curing of Mizori’s adhesive composition when it is cured, and for optimizing toughness and thermal stability of Mizori’s adhesive composition.
Regarding claim 10, Mizori teaches that a wide variety of diamines are contemplated for use, such as for example, bis(4-amino-3,5-dimethylphenyl)methane, bis(4-amino-3,5-diethylphenyl)methane, bis(4-amino-3-methylphenyl)methane, bis(4-amino-3-ethylphenyl)methane, 4,4'-oxydianiline, 4,4'-diaminodiphenyl sulfide, or 2,2-bis(4-(4-aminophenoxy)phenyl)propane [0137], and that a wide variety of anhydrides are contemplated for use, such as, for example, 4,4'-bisphenol A diphthalic anhydride [0140], which optionally reads on wherein X1 in the formula (3) is -C(CH3)2-, and the divalent aromatic group represented by A1 and A2 being expressed by the formula (4) or (5), wherein X1 is as defined in the formula (3), wherein X1 is as defined in the formula (3), wherein X1 independently represents a divalent group, the divalent group represented by X1 being selected from the following formulae,
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as claimed.
Mizori does not teach a specific embodiment wherein X1 in the formula (3) is -CH2- or -C(CH3)2-. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select at least one of Mizori’s bis(4-amino-3,5-dimethylphenyl)methane, bis(4-amino-3,5-diethylphenyl)methane, bis(4-amino-3-methylphenyl)methane, bis(4-amino-3-ethylphenyl)methane, 4,4'-oxydianiline, 4,4'-diaminodiphenyl sulfide, or 2,2-bis(4-(4-aminophenoxy)phenyl)propane as Mizori’s diamine that is contacted with Mizori’s dianhydride to produce Mizori’s imide-extended bismaleimide compound, and to select Mizori’s 4,4'-bisphenol A diphthalic anhydride as Mizori’s dianhydride that is contacted with Mizori’s diamine to produce Mizori’s imide-extended bismaleimide compound. The proposed modification would read on wherein X1 in the formula (3) is -C(CH3)2-, and the divalent aromatic group represented by A1 and A2 being expressed by the formula (4) or (5), wherein X1 is as defined in the formula (3), wherein X1 is as defined in the formula (3), wherein X1 independently represents a divalent group, the divalent group represented by X1 being selected from the following formulae,
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as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for providing a species of diamine and a species of dianhydride that are suitable for producing Mizori’s imide-extended bismaleimide compound or because it would have been obvious to try with a reasonable expectation of success because Mizori teaches that the imide-extended bismaleimide compound is produced by contacting a dianhydride with a diamine under conditions suitable to form an imide having terminal amino moieties, and contacting the terminal amino moieties with maleic anhydride under conditions suitable to form a maleimide, thereby producing an imide-extended bismaleimide monomer [0020], that a wide variety of diamines are contemplated for use, such as for example, bis(4-amino-3,5-dimethylphenyl)methane, bis(4-amino-3,5-diethylphenyl)methane, bis(4-amino-3-methylphenyl)methane, bis(4-amino-3-ethylphenyl)methane, 4,4'-oxydianiline, 4,4'-diaminodiphenyl sulfide, or 2,2-bis(4-(4-aminophenoxy)phenyl)propane [0137], and that a wide variety of anhydrides are contemplated for use, such as, for example, 4,4'-bisphenol A diphthalic anhydride [0140]. Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)).
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.
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/DAVID T KARST/ Primary Examiner, Art Unit 1767