DETAILED ACTION
Applicant’s response filed on 04/22/2026 has been fully considered. Claims 1-10 are pending. Claim 1 is amended.
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.
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
PNG
media_image1.png
142
726
media_image1.png
Greyscale
, 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], wherein 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], wherein 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], wherein 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], 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 in an amount of from 0.05 to 98% by mass, 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,
PNG
media_image2.png
76
60
media_image2.png
Greyscale
, 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,
PNG
media_image2.png
76
60
media_image2.png
Greyscale
PNG
media_image3.png
74
58
media_image3.png
Greyscale
, 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,
PNG
media_image4.png
28
84
media_image4.png
Greyscale
PNG
media_image5.png
18
58
media_image5.png
Greyscale
PNG
media_image6.png
16
56
media_image6.png
Greyscale
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 from 10 wt % to about 90 wt % based on total weight of 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,
PNG
media_image2.png
76
60
media_image2.png
Greyscale
, 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,
PNG
media_image2.png
76
60
media_image2.png
Greyscale
PNG
media_image3.png
74
58
media_image3.png
Greyscale
, 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,
PNG
media_image4.png
28
84
media_image4.png
Greyscale
PNG
media_image5.png
18
58
media_image5.png
Greyscale
PNG
media_image6.png
16
56
media_image6.png
Greyscale
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
PNG
media_image1.png
142
726
media_image1.png
Greyscale
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 with sufficient specificity that (A) the maleimide resin is in an amount of 5 to 95% 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 5 to 95 weight percent based on total weight of Mizori’s adhesive composition. The proposed modification would read on (A) the maleimide resin is in an amount of 5 to 95% 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 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 in an amount of 3 to 50 parts by mass per 100 parts by mass of the sum total of the components (A) and (B), 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, 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 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 in an amount of 10 to 50 parts by mass per 100 parts by mass of the sum total of the components (A) and (B) 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], 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 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,
PNG
media_image2.png
76
60
media_image2.png
Greyscale
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,
PNG
media_image2.png
76
60
media_image2.png
Greyscale
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)).
Response to Arguments
Applicant's arguments filed 04/22/2036 have been fully considered but they are not persuasive. In response to the applicant’s argument that the newly added numerical limitations clarify the compositional balance that enables the advantageous compatibility, film-forming properties, and handling characteristics achieved by the invention, and that neither Mizori nor Domeier discloses or suggests these specific quantitative requirements, nor do they provide any indication that such ranges would contribute to the superior performance demonstrated in the Examples in the specification (p. 6), Mizori in view of Domeier renders obvious the newly added numerical limitations and the specific quantitative requirements. Specifically, 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 5 to 95 weight percent based on total weight of Mizori’s adhesive composition. The proposed modification would read on (A) the maleimide resin is in an amount of 5 to 95% 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. Also, 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 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 in an amount of 10 to 50 parts by mass per 100 parts by mass of the sum total of the components (A) and (B) 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], 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 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], 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. It is noted that advantageous compatibility, film-forming properties, and handling characteristics are not recited in the rejected claims. 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).
In response to the applicant’s argument that there is no proper motivation to combine Mizori and Domeier (p. 6), one of ordinary skill in the art would have been motivated to combine Mizori and Domeier by using 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 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 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], 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.
In response to the applicant’s argument that the mere presence of similar classes of components does not establish that a person of ordinary skill in the art would have combined Mizori and Domeier for the purpose of achieving the present invention (p. 6), the Office’s reasoning for why one of ordinary skill in the art would have been motivated to combine Mizori and Domeier is not the presence of similar classes of components. The Office’s reasoning is that 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 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], 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.
In response to the applicant’s argument that Domeier contains no teaching or suggestion regarding dielectric properties (p. 6-7), it is noted that dielectric properties are not recited in the rejected claims. 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).
In response to the applicant’s argument that Domeier does not provide any indication that triallyl isocyanurate should be selected from among the many coreactants for the purpose of improving dielectric performance (p. 6-7), it is noted that dielectric performance is not recited in the rejected claims. 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). Each species of Domeier’s coreactant is a specific embodiment of Domeier’s coreactant being that species of coreactant. Domeier teaches a specific embodiment of their liquid coreactant (4:38-39) being triallyl isocyanurate (4:44-45). Domeier teaches benefits of using their triallyl isocyanurate, and Domeier teaches using allyl functional compounds in their composition [0160]. Specifically, 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.
In response to the applicant’s argument that Domeier merely provides a laundry list of components so that the Examiner’s proposed selection of particular components without any real scientific or fact basis reveals that the Examiner’s rejection is a classic hindsight combination of teachings from discrete references without any basis or motivation in the prior art for such a combination (p. 7), each species of Domeier’s coreactant is a specific embodiment of Domeier’s coreactant being that species of coreactant. Domeier teaches a specific embodiment of their liquid coreactant (4:38-39) being triallyl isocyanurate (4:44-45). Domeier provides motivation of using their triallyl isocyanurate, and Domeier teaches using allyl functional compounds in their composition [0160]. Specifically, 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.
In response to the applicant’s argument that the hindsight nature of the Examiner’s rejection is even more clear when it is noted that the Examiner provides no scientific or practical reason for a POSITA to be motivated to make the combination as proposed in the Office action (p. 7), it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971). One of ordinary skill in the art would have been motivated to combine Mizori and Domeier 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.
In response to the applicant’s argument that the compositions of the present invention, on the other hand, are designed to provide products with high glass-transition temperature, Tg, an excellent dielectric property, and an excellent dimensional stability, and to provide uncured and cured resin films having an excellent handling property, and that a POSITA would have had no reason to consult Domeier for improving dielectric properties (p. 7-8), it is noted that high glass-transition temperature, Tg, an excellent dielectric property, an excellent dimensional stability, uncured and cured resin films having an excellent handling property, and improving dielectric properties are not recited in the rejected claims. 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).
In response to the applicant’s argument that the Examiner’s assertion that the references are analogous art does not establish any proper motivation for a POSITA to combine the references (p. 8), the Office’s assertion that Mizori and Domeier are analogous art is not the Office’s reasoning for why one of ordinary skill in the art would have been motivated to combine Mizori and Domeier. The Office’s reasoning for why one of ordinary skill in the art would have been motivated to combine Mizori and Domeier is 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.
In response to the applicant’s argument that Mizori does not suggest that the resin should have a number-average molecular weight of 3000 or more, and that to the contrary, Mizori explicitly states that the oligomers of the invention usually have a molecular weight up to about 3,000 in paragraph [0055], indicating that molecular weights above 3000 are not typical or expected (p. 8), although Mizori teaches that oligomers of the invention typically have 2 to about 100 repeating monomer units, frequently 2 to about 30 repeating monomer units, and often 2 to about 10 repeating monomer units, and usually have a molecular weight up to about 3,000 [0055], this teaching of Mizori is not a requirement that their imide-extended bismaleimide compounds have a molecular weight up to about 3,000 because Mizori recites the words “usually” and “frequently”. Mizori also does not require their imide-extended bismaleimide to be an oligomer. Mizori’s embodiment that is the basis for the rejection of the claims set forth in this Office action is Mizori’s teaching that the imide-extended bismaleimide compounds have the structure
PNG
media_image1.png
142
726
media_image1.png
Greyscale
, 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], which does not limit the upper limit of the number average molecular weight of Mizori’s imide-extended bismaleimide compounds, and which means that the minimum of its number average molecular weight is 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.
In response to the applicant’s argument that a POSITA would understand Mizori as discouraging the use of high-molecular-weight maleimide resins of the type required by the present invention, and that this constitutes a clear teaching away, and one skilled in the art would not have been motivated to select the claimed high-molecular-weight maleimide resin (p. 8), Mizori suggests selecting a maleimide resin having a number average molecular weight of not lower than 3,000. Specifically, Mizori teaches that the bismaleimide compounds are imide-extended bismaleimide compounds having the structure
PNG
media_image1.png
142
726
media_image1.png
Greyscale
, 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], which reads on the maleimide resin having a number average molecular weight of not lower than 1,729.72. 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. One of ordinary skill in the art would have been motivated to select Mizori’s n in Mizori’s structure
PNG
media_image1.png
142
726
media_image1.png
Greyscale
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)). Also, one of ordinary skill in the art would have been motivated 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) 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)).
In response to the applicant’s argument that a POSITA would not have had any reasonable expectation of success in selecting the claimed high-molecular-weight maleimide resin (p. 8), one of ordinary skill in the art would have had a reasonable expectation of success in selecting Mizori’s n in Mizori’s structure
PNG
media_image1.png
142
726
media_image1.png
Greyscale
to be an integer having the value from 4 to about 10, which 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, because Mizori teaches that the bismaleimide compounds are imide-extended bismaleimide compounds having the structure
PNG
media_image1.png
142
726
media_image1.png
Greyscale
, 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], which reads on the maleimide resin optionally having a number average molecular weight of not lower than 1,729.72. 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. Based on Mizori’s teachings, there is no upper limit for their molecular weight, and it can optionally be within the claimed range of not lower than 3,000. This is because Mizori suggests selecting 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, as explained in the rejection of claim 1 set forth in this Office action. Also, Mizori suggests selecting Mizori’s n in Mizori’s structure
PNG
media_image1.png
142
726
media_image1.png
Greyscale
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.
In response to the applicant’s argument that Mizori and Domeier do not provide any teaching regarding compatibility between (A) a maleimide resin represented by the following formula (3) and having a number average molecular weight of not lower than 3,000 and (B) an organic compound having, in one molecule, at least one allyl group and at least on isocyanuric ring (p. 8), one of ordinary skill in the art would have had a reasonable expectation of success, based on Mizori’s and Domeier’s teachings, that the resulting (A) and (B) would be compatible. This is because 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 suggests using any allyl functional comonomer in Mizori’s composition, such as that of Domeier. Also, Domeier teaches that their triallyl isocyanurate (4:44-45) is a liquid coreactant in a composition (4:38-39) and 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), which suggests using their triallyl isocyanurate in a composition comprising a bismaleimide, such as that of Mizori,
In response to the applicant’s argument that there is no suggestion that the combination of Mizori and Domeier would yield excellent film uniformity before and after curing, mechanical durability, or dielectric properties suitable for high-frequency applications, and that the present invention achieves a level of compatibility and film performance that cannot be inferred or expected from the disclosures of Mizori or Domeier (p. 8-9), it is noted that excellent film uniformity before and after curing, mechanical durability, dielectric properties, high-frequency applications, compatibility, and film performance are not recited in the rejected claims. 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). Also, one of ordinary skill in the art would have had a reasonable expectation of success that combining Mizori and Domeier would have compatibility as explained in the previous paragraph.
In response to the applicant’s argument that the present application provides clear evidence of unexpected results based on Table 3 of the specification of the instant application (p. 9), the applicant’s arguments of unexpected results are not persuasive because the applicant’s results in Table 3 are not commensurate in scope with the claimed invention. This is because claim 1 limits the maleimide resin to being represented by the claimed formula (3), having a number average molecular weight of not lower than 3,000 and being in an amount of 5 to 95% by mass, limits the organic compound having, in one molecule, at least on allyl group and at least one isocyanuric ring to being in an amount of 3 to 50 parts by mass per 100 parts by mass of the sum of (A) and (B), does not limit the species of the organic compound, does not limit the species and amount of the reaction initiator, and does not exclude the composition from further comprising ingredients not recited in claim 1. The applicant’s results in Table 3 of the specification of the instant application comprise only one Working example, which is Working example 6, which comprises one species of the maleimide resin of formula (3), one number average molecular weight, one amount of the maleimide resin, one species and one amount of the organic compound, one species and one amount of the reaction initiator, and does not further comprise ingredients not recited in claim 1 (specification p. 42). The applicant did not show that the results of Working example 6 would occur for all species of the maleimide resin of formula (3), for any number average molecular weight of not lower than 3,000, for all amount of the maleimide resin of 5 to 95% by mass, for any species of at least on allyl group and at least one isocyanuric ring in any amount of 3 to 50 parts by mass per 100 parts by mass of the sum of (A) and (B), for any amount and any species of reaction initiator, and for any further ingredient in the composition. Whether the unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the "objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support (MPEP 716.02(d))." In other words, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range (MPEP 716.02(d)). Since the applicant only showed one working example in Table 3, the applicant did not show a sufficient number of examples that would allow one of ordinary skill in the art to determine a trend in the exemplified data that would allow the artisan to extend the probative value thereof over the entire scope of claim 1. The nonobviousness of a broader claimed range can be supported by evidence based on unexpected results from testing a narrower range if one of ordinary skill in the art would be able to determine a trend in the exemplified data which would allow the artisan to reasonably extend the probative value thereof (MPEP 716.02(d)(I)). Since the applicant only showed one working example in Table 3, the applicant did not compare a sufficient number of examples within the scope of claim 1 with a sufficient number of examples outside the scope of claim 1. To establish unexpected results over a claimed range, applicants should compare a sufficient number of tests both inside and outside the claimed range to show the criticality of the claimed range (MPEP 716.02(d)(II)).
Conclusion
THIS ACTION IS MADE FINAL. 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