DETAILED ACTION
Priority
Applicant’s response filed on 10/14/2025 has been fully considered. Claims 1-21 are pending. Claims 14-18 are withdrawn.
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.
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, 2, 4, 6-8, 11, and 19 are rejected under 35 U.S.C. 103 as being unpatentable over Kramer et al. (US 2009/0264558 A1) in view of Agarwal et al. (US 2003/0104212 A1).
Regarding claim 1, Kramer teaches a heat-curing composition that has a constitution of 15.0 g of D.E.R.671 (A) ([0179], TABLE 3, Composition 1) that is solid resin with epoxy equivalent weight of 475-550 g/eq ([0161], TABLE 1), 30.0 g of DGEBA (A) ([0179], TABLE 3, Composition 1) that is D.E.R. 330 that is bisphenol A diglycidyl ether ([0161], TABLE 1), 3.0 g of DY-H (G) ([0179], TABLE 3, Composition 1) that is hexanediol diglycidyl ether ([0161], TABLE 1), 0.5 g of M1 (G) ([0179], TABLE 3, Composition 1) that is a monohydroxylated epoxide [0161, 0162], 10.0 g of Polydis (D) ([0179], TABLE 3, Composition 1) that is bisphenol F diglycidyl ether, modified nitrile-butadiene rubber ([0161], TABLE 1), 19.5 g of P1 ([0179], TABLE 3, Composition 1) that is a capped polyurethane polymer [0169] that has a formula [0165] that is an end-capped polyurethane prepolymer [0012] in which the functional groups of the end-caps differ from each other [0015], 3.0 g of UD (C) ([0179], TABLE 3, Composition 1) that is a urea derivative [0172], 10.0 g of blockPU ([0179], TABLE 3, Composition 1) that is a capped polyurethane prepolymer [0171], 4.4 g of dicy (D) ([0179], TABLE 3, Composition 1) that is dicyandiamide ([0161], TABLE 1), and 12.0 g of filler mixture (F) ([0179], TABLE 3, Composition 1), wherein the epoxy resin composition is suitable as a vehicle-body-shell adhesive [0011], wherein the epoxy resin is liquid epoxy resin [0083, 0097, 0102, 0104, 0105], wherein the (D) is a liquid rubber [0116, 0117, 0118, 0120, 0121, 0122], which reads on a liquid epoxy adhesive composition comprising (a) at least one epoxy resin, (d) one or more block polyurethane toughening agents, and (e) at least one heat-activated latent curing agent comprising dicyandiamide (DICY), wherein the one or more blocked polyurethane toughening agents comprises at least one asymmetrically end-capped polyurethane as claimed. Kramer teaches that the liquid rubber D is a carboxy- or epoxide-terminated polymer [0116], that the liquid rubber D is a carboxy- or epoxide-terminated acrylonitrile-butadiene copolymer, or a derivative thereof [0117], and that the Polydis is a liquid rubber D [0117], which suggests using Kramer’s carboxy-terminated acrylonitrile-butadiene copolymer to substitute for Kramer’s 10.0 g of Polydis (D) that is bisphenol F diglycidyl ether, modified nitrile-butadiene rubber, which would read on the liquid epoxy adhesive composition further comprising (b) one or more carboxyl-terminated butadiene acrylonitrile copolymers (CTBN) as claimed. Kramer teaches that the epoxy resin composition preferably further comprises a solid toughener E [0123], and that the solid toughener E is optionally a core-shell polymer composed of a core of elastic acrylate polymer or of elastic butadiene polymer with a surrounding rigid shell of a rigid thermoplastic polymer [0133], core-shell polymer particles having polysiloxane core and acrylate shell, or core-shell polymer particles that are radiation-crosslinked rubber particles [0134], which suggests using Kramer’s core-shell polymer composed of a core of elastic acrylate polymer or of elastic butadiene polymer with a surrounding rigid shell of a rigid thermoplastic polymer, core-shell polymer particles having polysiloxane core and acrylate shell, or core-shell polymer particles that are radiation-crosslinked rubber particles to modify Kramer’s heat-curing composition, which would read on the liquid epoxy adhesive composition further comprising (c) rubber particles, optionally including core-shell rubber particles as claimed. Kramer teaches that the composition further comprises at least one hardener B for epoxy resins [0108], that the materials here are preferably a hardener selected from dicyandiamide and substituted ureas [0108], that it is preferable that the hardener B involves a hardener selected from dicyandiamide, and substituted ureas [0109], which suggests using Kramer’s hardener B that is a hardener selected from substituted ureas to substitute for a fraction of Kramer’s 4.4 g of dicy (D) that is dicyandiamide, which would read on the liquid epoxy adhesive composition further comprising (f) at least one accelerator different from the curing agent as claimed. Kramer teaches that the composition optionally further comprises plasticizers [0152].
Kramer does not teach a specific embodiment of the liquid epoxy adhesive composition further comprising (b) one or more carboxyl-terminated butadiene homopolymers or butadiene acrylonitrile copolymers (CTBN). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Kramer’s carboxy-terminated acrylonitrile-butadiene copolymer to substitute for Kramer’s 10.0 g of Polydis (D) that is bisphenol F diglycidyl ether, modified nitrile-butadiene rubber. The proposed modification would read on the liquid epoxy adhesive composition further comprising (b) one or more carboxyl-terminated butadiene acrylonitrile copolymers (CTBN) as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying toughness of Kramer’s heat-curing composition because Kramer teaches that the heat-curing composition comprises 10.0 g of Polydis (D) ([0179], TABLE 3, Composition 1) that is bisphenol F diglycidyl ether, modified nitrile-butadiene rubber ([0161], TABLE 1), that the (D) is a liquid rubber [0116, 0117, 0118, 0120, 0121, 0122], that the liquid rubber D is a carboxy- or epoxide-terminated polymer [0116], that the liquid rubber D is a carboxy- or epoxide-terminated acrylonitrile-butadiene copolymer, or a derivative thereof [0117], and that the Polydis is a liquid rubber D [0117], and that liquid rubbers have a relatively long history of use as tougheners [0003].
Kramer does not teach a specific embodiment of the liquid epoxy adhesive composition further comprising (c) rubber particles, optionally including core-shell rubber particles and/or particles of size 500 nm or less. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Kramer’s core-shell polymer composed of a core of elastic acrylate polymer or of elastic butadiene polymer with a surrounding rigid shell of a rigid thermoplastic polymer, core-shell polymer particles having polysiloxane core and acrylate shell, or core-shell polymer particles that are radiation-crosslinked rubber particles to modify Kramer’s heat-curing composition. The proposed modification would read on the liquid epoxy adhesive composition further comprising (c) rubber particles, optionally including core-shell rubber particles as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for further modifying toughness of Kramer’s heat-curing composition and for modifying an ability of Kramer’s heat-curing composition to absorb flexural, tensile, or impact stresses before Kramer’s composition tears or fractures because Kramer teaches that the epoxy resin composition preferably further comprises a solid toughener E [0123], that the solid toughener E is optionally a core-shell polymer composed of a core of elastic acrylate polymer or of elastic butadiene polymer with a surrounding rigid shell of a rigid thermoplastic polymer [0133], core-shell polymer particles having polysiloxane core and acrylate shell, or core-shell polymer particles that are radiation-crosslinked rubber particles [0134], that the core-shell polymer is beneficial for being a solid toughener [0133], and that the toughener is beneficial for bringing about a marked increase in toughness, thus permitting absorption of higher flexural, tensile, or impact stresses before the matrix tears or fractures [0123].
Kramer does not teach a specific embodiment of the liquid epoxy adhesive composition further comprising (f) at least one accelerator different form the curing agent. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Kramer’s hardener B that is a hardener selected from substituted ureas to substitute for a fraction of Kramer’s 4.4 g of dicy (D) that is dicyandiamide. The proposed modification would read on the liquid epoxy adhesive composition further comprising (f) at least one accelerator different from the curing agent as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying hardening properties of Kramer’s heat-curing composition at an elevated temperature because Kramer teaches that the heat-curing composition comprises 4.4 g of dicy (D) ([0179], TABLE 3, Composition 1) that is dicyandiamide ([0161], TABLE 1), that the composition further comprises at least one hardener B for epoxy resins, where this hardener is activated via an elevated temperature [0108], that the materials here are preferably a hardener selected from dicyandiamide and substituted ureas [0108], and that it is preferable that the hardener B involves a hardener selected from dicyandiamide, and substituted ureas [0109].
Kramer does not teach that the liquid epoxy adhesive composition further comprises (g) a polyetheramine flexibilizer comprising a polyetheramine-DGEBA adduct. However, Agarwal teaches flexibilizing epoxy resins that are adducts of amine-terminated polyalkylene glycols and bisphenol A diglycidyl ethers and that are utilized [0017] in combination with at least one diglycidyl ether of bisphenol A [0016]. Kramer and Agarwal are analogous art because both references are in the same field of endeavor of a composition comprising at least one epoxy resin and optionally a flexibilizer. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Agarwal’s flexibilizing epoxy resins that are adducts of amine-terminated polyalkylene glycols and bisphenol A diglycidyl ethers to modify Kramer’s heat-curing composition. The proposed modification would read on the liquid epoxy adhesive composition further comprising (g) a polyetheramine flexibilizer comprising a polyetheramine-DGEBA adduct as claimed. One of ordinary skill in the art would have been motivated to do so because Agarwal teaches that the flexibilizing epoxy resins that are adducts of amine-terminated polyalkylene glycols and bisphenol A diglycidyl ethers are beneficial for being flexibilizing epoxy resins that may be utilized [0017] in combination with at least one diglycidyl ether of bisphenol A [0016], which would have been beneficial for modifying flexibility of Kramer’s heat-curing composition, which would have been desirable for Kramer’s heat-curing composition because Kramer teaches that the heat-curing composition has a constitution of D.E.R.671 (A) ([0179], TABLE 3, Composition 1) that is solid resin with epoxy equivalent weight of 475-550 g/eq ([0161], TABLE 1), DGEBA (A) ([0179], TABLE 3, Composition 1) that is D.E.R. 330 that is bisphenol A diglycidyl ether ([0161], TABLE 1), Polydis (D) ([0179], TABLE 3, Composition 1) that is bisphenol F diglycidyl ether ([0161], TABLE 1), and optionally plasticizers [0152].
Regarding claim 2, Kramer teaches that the heat-curing composition has a constitution of 30.0 g of DGEBA (A) ([0179], TABLE 3, Composition 1) that is D.E.R. 330 that is bisphenol A diglycidyl ether ([0161], TABLE 1), which reads on wherein the components (a) comprise one diglycidyl ether of a bisphenol-A (DGEBA) epoxy resins, optionally having a quantity range of from 20 wt.% or 60 wt.% as claimed since the optional limitation is optional. Kramer teaches that the heat-curing composition has a constitution 10.0 g of Polydis (D) ([0179], TABLE 3, Composition 1) that is bisphenol F diglycidyl ether, modified nitrile-butadiene rubber ([0161], TABLE 1), that the liquid rubber D is a carboxy- or epoxide-terminated polymer [0116], that the liquid rubber D is a carboxy- or epoxide-terminated acrylonitrile-butadiene copolymer, or a derivative thereof [0117], and that the Polydis is a liquid rubber D [0117], which suggests using Kramer’s carboxy-terminated acrylonitrile-butadiene copolymer to substitute for Kramer’s 10.0 g of Polydis (D) that is bisphenol F diglycidyl ether, modified nitrile-butadiene rubber, which would read on wherein the component (b) comprises (b) one or more carboxyl-terminated butadiene acrylonitrile copolymers (CTBN), optionally having a quantity range of from 1 wt.% to 8 wt.% as claimed since the optional limitation is optional. As explained above for claim 1, before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Kramer’s core-shell polymer composed of a core of elastic acrylate polymer or of elastic butadiene polymer with a surrounding rigid shell of a rigid thermoplastic polymer, core-shell polymer particles having polysiloxane core and acrylate shell, or core-shell polymer particles that are radiation-crosslinked rubber particles to modify Kramer’s heat-curing composition, which renders obvious wherein the component (c) comprises (c) core shell rubber (CSR) particles, optionally having a quantity range of from 5 wt.% to 30 wt.% as claimed since the optional limitation is optional. Kramer teaches a heat-curing composition that has a constitution of 19.5 g of P1 ([0179], TABLE 3, Composition 1) that is a capped polyurethane polymer [0169] that has a formula [0165] that is an end-capped polyurethane prepolymer [0012] in which the functional groups of the end-caps differ from each other [0015], and 10.0 g of blockPU ([0179], TABLE 3, Composition 1) that is a capped polyurethane prepolymer [0171], which reads on wherein the component (d) comprises (d) one or more block polyurethane toughening agents, optionally having a quantity range of from 5 wt.% to 20 wt.% as claimed since the optional limitation is optional. Kramer teaches that the heat-curing composition has a constitution of 4.4 g of dicy (D) ([0179], TABLE 3, Composition 1) that is dicyandiamide ([0161], TABLE 1), which reads on wherein the component (e) comprises (e) one or more dicyandiamides (DICY), optionally having a quantity range of from 2 wt.% to 6 wt.% as claimed since the optional limitation is optional. As explained above for claim 1, before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Kramer’s hardener B that is a hardener selected from substituted ureas to substitute for a fraction of Kramer’s 4.4 g of dicy (D) that is dicyandiamide, and Kramer teaches that the materials here are preferably a hardener selected from dicyandiamide and substituted ureas [0108], and that it is preferable that the hardener B involves a hardener selected from dicyandiamide, and substituted ureas [0109], which renders obvious wherein the component (f) comprises (f) one or more urea-based accelerator, optionally having a quantity range of from 0.5 wt.% to 2.0 wt.% as claimed since the optional limitation is optional. Kramer teaches that the composition optionally further comprises plasticizers [0152].
Kramer does not teach that the component (g) comprises: (g) the polyetheramine flexibilizer comprising a polyetheramine-DGEBA adduct in an amount of up to 12 wt.%. However, Agarwal teaches flexibilizing epoxy resins that are adducts of amine-terminated polyalkylene glycols and bisphenol A diglycidyl ethers and that are utilized [0017] in combination with at least one diglycidyl ether of bisphenol A [0016], wherein the ratio of flexibilizing epoxy resin: bisphenol A diglycidyl ether may suitably be from about 0.05 to about 0.40, as calculated from the epoxide equivalent weight of each component [0016]. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Agarwal’s flexibilizing epoxy resins that are adducts of amine-terminated polyalkylene glycols and bisphenol A diglycidyl ethers to modify Kramer’s heat-curing composition, and to optimize the amount of Agarwal’s flexibilizing epoxy resins that are adducts of amine-terminated polyalkylene glycols and bisphenol A diglycidyl ethers in Kramer’s heat-curing composition to be up to 12 g per 100 g of the total amount of the heat-curing composition. The proposed modification would read on wherein the component (g) comprises: (g) the polyetheramine flexibilizer comprising a polyetheramine-DGEBA adduct in an amount of up to 12 wt.% as claimed. One of ordinary skill in the art would have been motivated to do so because Agarwal teaches that the flexibilizing epoxy resins that are adducts of amine-terminated polyalkylene glycols and bisphenol A diglycidyl ethers are beneficial for being flexibilizing epoxy resins that may be utilized [0017] in combination with at least one diglycidyl ether of bisphenol A [0016], which would have been beneficial for modifying flexibility of Kramer’s heat-curing composition, which would have been desirable for Kramer’s heat-curing composition because Kramer teaches that the heat-curing composition has a constitution of 15.0 g of D.E.R.671 (A) ([0179], TABLE 3, Composition 1) that is solid resin with epoxy equivalent weight of 475-550 g/eq ([0161], TABLE 1), 30.0 g of DGEBA (A) ([0179], TABLE 3, Composition 1) that is D.E.R. 330 that is bisphenol A diglycidyl ether ([0161], TABLE 1), 3.0 g of DY-H (G) ([0179], TABLE 3, Composition 1) that is hexanediol diglycidyl ether ([0161], TABLE 1), 0.5 g of M1 (G) ([0179], TABLE 3, Composition 1) that is a monohydroxylated epoxide [0161, 0162], 10.0 g of Polydis (D) ([0179], TABLE 3, Composition 1) that is bisphenol F diglycidyl ether, modified nitrile-butadiene rubber ([0161], TABLE 1), 19.5 g of P1 ([0179], TABLE 3, Composition 1) that is a capped polyurethane polymer [0169] that has a formula [0165] that is an end-capped polyurethane prepolymer [0012] in which the functional groups of the end-caps differ from each other [0015], 3.0 g of UD (C) ([0179], TABLE 3, Composition 1) that is a urea derivative [0172], 10.0 g of blockPU ([0179], TABLE 3, Composition 1) that is a capped polyurethane prepolymer [0171], 4.4 g of dicy (D) ([0179], TABLE 3, Composition 1) that is dicyandiamide ([0161], TABLE 1), and 12.0 g of filler mixture (F) ([0179], TABLE 3, Composition 1), and that the composition optionally further comprises plasticizers [0152], which means that the amount of Agarwal’s flexibilizing epoxy resins that are adducts of amine-terminated polyalkylene glycols and bisphenol A diglycidyl ethers in Kramer’s heat-curing composition in g per 100 g of the total amount of the heat-curing composition would have affected plasticity and/or flexibility of the heat-curing composition, which means that optimizing the amount of Agarwal’s flexibilizing epoxy resins that are adducts of amine-terminated polyalkylene glycols and bisphenol A diglycidyl ethers in Kramer’s heat-curing composition in g per 100 g of the total amount of the heat-curing composition would have been beneficial for optimizing plasticity and/or flexibility of the heat-curing composition.
Kramer in view of Agarwal renders obvious the “optional” limitations of claim 2 as claimed because they are optional limitations.
Regarding claim 4, as explained above for claim 1, Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Kramer’s carboxy-terminated acrylonitrile-butadiene copolymer to substitute for Kramer’s 10.0 g of Polydis (D) that is bisphenol F diglycidyl ether, modified nitrile-butadiene rubber, which renders obvious wherein the one or more carboxyl-terminated butadiene acrylonitrile (CTBN) comprises a copolymer of butadiene and a nitrile monomer, optionally including acrylonitrile as claimed.
Regarding claim 6, Kramer teaches that the heat-curing composition comprises 30.0 g of DGEBA (A) ([0179], TABLE 3, Composition 1) that is D.E.R. 330 that is bisphenol A diglycidyl ether ([0161], TABLE 1), that the epoxy resin composition preferably further comprises a solid toughener E [0123], and that the solid toughener E is optionally a core-shell polymer composed of a core of elastic butadiene polymer with a surrounding rigid shell of a rigid thermoplastic polymer [0133], which suggests using Kramer’s core-shell polymer composed of a core of elastic butadiene polymer with a surrounding rigid shell of a rigid thermoplastic polymer to modify Kramer’s heat-curing composition, which would read on wherein the core shell rubber (CSR) particles (c) have a core comprising, consisting essentially or, or consisting of polybutadiene and/or (d) are dispersed in DGEBA epoxy resin as claimed.
Kramer does not teach a specific embodiment wherein the core shell rubber (CSR) particles (a), (b), (c), and/or (d) as claimed. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Kramer’s core-shell polymer composed of a core of elastic butadiene polymer with a surrounding rigid shell of a rigid thermoplastic polymer to modify Kramer’s heat-curing composition. The proposed modification would read on wherein the core shell rubber (CSR) particles (c) have a core comprising, consisting essentially or, or consisting of polybutadiene and/or (d) are dispersed in DGEBA epoxy resin as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for further modifying toughness of Kramer’s heat-curing composition and for modifying an ability of Kramer’s heat-curing composition to absorb flexural, tensile, or impact stresses before Kramer’s composition tears or fractures because Kramer teaches that the epoxy resin composition preferably further comprises a solid toughener E [0123], that the solid toughener E is optionally a core-shell polymer composed of a core of elastic butadiene polymer with a surrounding rigid shell of a rigid thermoplastic polymer [0133], that the core-shell polymer is beneficial for being a solid toughener [0133], and that the toughener is beneficial for bringing about a marked increase in toughness, thus permitting absorption of higher flexural, tensile, or impact stresses before the matrix tears or fractures [0123].
Regarding claim 7, Kramer teaches that the heat-curing composition comprises 19.5 g of P1 ([0179], TABLE 3, Composition 1) that is a capped polyurethane polymer [0169] that has a formula [0165] that is an end-capped polyurethane prepolymer [0012] in which the functional groups of the end-caps differ from each other [0015], wherein the P1 is produced from 247.6 g of PU1-1 and 117.9 g of M1, wherein 90 mol % of NCO groups are capped with the capping agent M1 in the polyurethane prepolymer PU1-1, wherein 10 mol % of the NCO groups are capped with the capping agent NC in the polyurethane prepolymer PU1-1 ([0167], Table 2, P1), wherein the PU1-1 is an isocyanate-terminated polyurethane prepolymer that is prepared [0163] from 200.00 g of Desmophen 3060 BS, 47.55 g of IPDI, and 25 mg of dibutyltin dilaurate [0164], wherein the Desmophen 3060 B2 is trifunctional polypropylene glycol with an OH-equivalent weight of 1000 g/OH-equivalent, wherein the IPDI is isophorone diisocyanate ([0161], TABLE 1) wherein the M1 is monohydroxylated epoxide [0161], wherein the NC is cardanol [0169], which reads on wherein the one or more blocked polyurethane toughening agent comprises a polyalkylene glycol segment, and has an equivalent molecular weight that is 1000 Daltons, and the polyurethane toughening agent is end capped at both ends. Kramer teaches that the polyurethane prepolymer PU1 can be produced from a polymer QPM having terminal hydroxy groups [0032], that polymers QPM advantageously have an equivalent weight of from 300 to 6000 g/equivalent of NCO-reactive groups [0038], and that suitable polymers QPM are polyols, such as the following commercially available polyols: [0039] polyoxypropylenediols [0040], which suggests using Kramer’s polyols that are polyoxypropylenediols that have an equivalent weight that is optimized to be from 2000 to 5000 g/equivalent of NCO-reactive groups to substitute for Kramer’s Desmophen 3060 BS that is used to produce Kramer’s capped polyurethane polymer P1, which would read on wherein the one or more blocked polyurethane toughening agent comprises a polyalkylene glycol segment, and has an equivalent molecular weight in a range of from 2000-5000 Daltons, and the polyurethane toughening agent is end capped at both ends as claimed.
Kramer does not teach a specific embodiment wherein the one or more blocked polyurethane toughening agent has an equivalent molecular weight in a range of from 2000-5000 Daltons. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Kramer’s polyols that are polyoxypropylenediols that have an equivalent weight that is optimized to be from 2000 to 5000 g/equivalent of NCO-reactive groups to substitute for Kramer’s Desmophen 3060 BS that is used to produce Kramer’s capped polyurethane polymer P1. The proposed modification would read on wherein the one or more blocked polyurethane toughening agent comprises a polyalkylene glycol segment, and has an equivalent molecular weight in a range of from 2000-5000 Daltons, and the polyurethane toughening agent is end capped at both ends as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying impact resistance of Kramer’s heat-curing composition and for optimizing an extent of reaction of Kramer’s polyols that are reacted to produce Kramer’s capped polyurethane polymer P1 because Kramer teaches that the heat-curing composition comprises 19.5 g of P1 ([0179], TABLE 3, Composition 1) that is a capped polyurethane polymer [0169] that has a formula [0165] that is an end-capped polyurethane prepolymer [0012] in which the functional groups of the end-caps differ from each other [0015], wherein the P1 is produced from 247.6 g of PU1-1 and 117.9 g of M1, wherein 90 mol % of NCO groups are capped with the capping agent M1 in the polyurethane prepolymer PU1-1, wherein 10 mol % of the NCO groups are capped with the capping agent NC in the polyurethane prepolymer PU1-1 ([0167], Table 2, P1), wherein the PU1-1 is an isocyanate-terminated polyurethane prepolymer that is prepared [0163] from 200.00 g of Desmophen 3060 BS, 47.55 g of IPDI, and 25 mg of dibutyltin dilaurate [0164], wherein the Desmophen 3060 B2 is trifunctional polypropylene glycol with an OH-equivalent weight of 1000 g/OH-equivalent, wherein the IPDI is isophorone diisocyanate ([0161], TABLE 1) wherein the M1 is monohydroxylated epoxide [0161], wherein the NC is cardanol [0169], that the polyurethane prepolymer PU1 can be produced from a polymer QPM having terminal hydroxy groups [0032], that polymers QPM advantageously have an equivalent weight of from 300 to 6000 g/equivalent of NCO-reactive groups [0038], that suitable polymers QPM are polyols, such as the following commercially available polyols: [0039] polyoxypropylenediols [0040], that the use of polyurethane prepolymers capped asymmetrically gives impact resistances that are higher than those obtained using polyurethane prepolymers known from the prior art, capped symmetrically [0009], and that the end-capped polyurethane prepolymers are used as impact modifiers in the epoxy resin composition [0010], which means that an equivalent weight of Kramer’s polyols that are polyoxypropylenediols in g/equivalent of NCO-reactive groups would have affected an extent of reaction of Kramer’s polyols that are reacted to produce Kramer’s capped polyurethane polymer P1.
Kramer in view of Agarwal renders obvious the “optional” limitations of claim 7 because they are optional.
Regarding claim 8, Kramer teaches that the heat-curing composition comprises 19.5 g of P1 ([0179], TABLE 3, Composition 1) that is a capped polyurethane polymer [0169] that has a formula [0165] that is an end-capped polyurethane prepolymer [0012] in which the functional groups of the end-caps differ from each other [0015], wherein the P1 is produced from 247.6 g of PU1-1 and 117.9 g of M1, wherein 90 mol % of NCO groups are capped with the capping agent M1 in the polyurethane prepolymer PU1-1, wherein 10 mol % of the NCO groups are capped with the capping agent NC in the polyurethane prepolymer PU1-1 ([0167], Table 2, P1), wherein the PU1-1 is an isocyanate-terminated polyurethane prepolymer that is prepared [0163] from 200.00 g of Desmophen 3060 BS, 47.55 g of IPDI, and 25 mg of dibutyltin dilaurate [0164], wherein the Desmophen 3060 B2 is trifunctional polypropylene glycol with an OH-equivalent weight of 1000 g/OH-equivalent, wherein the IPDI is isophorone diisocyanate ([0161], TABLE 1) wherein the M1 is monohydroxylated epoxide [0161], wherein the NC is cardanol [0169], which reads on wherein each end cap is independently monohydroxylated epoxide or cardanol. Kramer teaches that the capping agents are optionally a monohydroxyepoxide compound of the formula
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and R3-H [0079], wherein R4 is optionally a moiety of an aromatic epoxide containing a primary hydroxyl group, after the removal of the hydroxide and epoxide groups, and p is optionally 1 [0014], wherein R3 is a moiety that is optionally
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or
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[0018], where in each case, R15 and R16, independently of the others, is optionally H [0022], wherein R18 is optionally phenol, cardanol, bisphenol A, or bisphenol F [0024], which suggests using Kramer’s capping agents that are a monohydroxyepoxide compound of the formula
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and R3-H, wherein R4 is a phenylene moiety, wherein R3 is a moiety that is
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or
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, where in each case, R15 and R16, independently of the others, is H, wherein R18 is bisphenol A or bisphenol F, to substitute for Kramer’s capping agents that are monohydroxylated epoxide and cardanol and that are used to produce Kramer’s capped polyurethane polymer P1, which would read on wherein each end cap is independently a substituted phenol or bisphenol, and/or pyrazole as claimed.
Kramer does not teach a specific embodiment wherein each end cap is independently a substituted phenol or bisphenol or a hydroxyheteroaryl analog thereof, an amine, methacryl, acetoxy, oxime, and/or pyrazole. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Kramer’s capping agents that are a monohydroxyepoxide compound of the formula
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and R3-H, wherein R4 is a phenylene moiety, wherein R3 is a moiety that is
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or
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, where in each case, R15 and R16, independently of the others, is H, wherein R18 is bisphenol A or bisphenol F, to substitute for Kramer’s capping agents that are monohydroxylated epoxide and cardanol and that are used to produce Kramer’s capped polyurethane polymer P1. The proposed modification would read on wherein each end cap is independently a substituted phenol or bisphenol, and/or pyrazole as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying impact resistance of Kramer’s heat-curing composition because Kramer teaches that 90 mol % of NCO groups are capped with the capping agent M1 in the polyurethane prepolymer PU1-1, that 10 mol % of the NCO groups are capped with the capping agent NC in the polyurethane prepolymer PU1-1 ([0167], Table 2, P1), that the capping agents are optionally a monohydroxyepoxide compound of the formula
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and R3-H [0079], wherein R4 is optionally a moiety of an aromatic epoxide containing a primary hydroxyl group, after the removal of the hydroxide and epoxide groups, and p is optionally 1 [0014], wherein R3 is a moiety that is optionally
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or
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[0018], where in each case, R15 and R16, independently of the others, is optionally H [0022], wherein R18 is optionally phenol, cardanol, bisphenol A, or bisphenol F [0024], that use of polyurethane prepolymers capped asymmetrically, i.e. using different capping agents, gives impact resistances that are higher than those obtained using polyurethane prepolymers known from the prior art, capped symmetrically, i.e. using identical capping agent [0009], and that the end-capped polyurethane prepolymers are used as impact modifiers in epoxy resin compositions [0010].
Regarding claim 11, Kramer renders obvious wherein the one or more filler comprises one or more of calcium carbonate, calcium oxide, calcium silicate, aluminosilicate, organophilic phyllosilicates, naturally occurring clays, silica, mica, talc, microspheres, or hollow glass microspheres, chopped or milled fibers optionally comprising carbon, glass, or aramid fibers, pigments, natural and/or synthetic zeolites, or thermoplastic fillers as claimed because claims 2 and 11 do not require the one or more filler to be present because the liquid epoxy adhesive composition optionally further comprises (g) one or more filler, optionally having a quantity range of from 0 wt.% to 20 wt.%.
Regarding claim 19, Kramer teaches a test specimen produced from the heat-curing composition, wherein a layer of the heat-curing composition is placed on electrolytically galvanized DC04 steel, and the heat-curing composition is cured [0175, 0178], which reads on an article of manufacturing comprising the liquid epoxy adhesive composition of claim 1, as applied on at least one surface of the article and uncured, or cured on the at least one surface of the article as claimed. Kramer in view of Agarwal renders obvious the “optional” limitation of claim 19 because it is optional.
Claim 3 is rejected under 35 U.S.C. 103 as being unpatentable over Kramer et al. (US 2009/0264558 A1) in view of Agarwal et al. (US 2003/0104212 A1) as applied to claim 2, and further as evidenced by Dow (Dow, “D.E.R. 330”, October 2001).
Regarding claim 3, Kramer in view of Agarwal renders obvious the liquid epoxy adhesive composition of claim 2 as explained above. Kramer teaches that the heat-curing composition comprises 30.0 g of DGEBA (A) ([0179], TABLE 3, Composition 1) that is D.E.R. 330 that is bisphenol A diglycidyl ether ([0161], TABLE 1). Dow provides evidence that D.E.R. 330 is a liquid epoxy resin that is a reaction product of epichlorohydrin and bisphenol-A and that has an epoxide equivalent weight of 176 – 185 g/eq (p. 1). Kramer in view of Agarwal and as evidenced by Dow therefore renders it obvious, wherein the diglycidyl ether of the bisphenol-A (DGEBA) epoxy resin has an Epoxy Equivalent Weight (EEW) in a range of from 176 to 185 where
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, which reads on the claimed range.
Claim 5 is rejected under 35 U.S.C. 103 as being unpatentable over Kramer et al. (US 2009/0264558 A1) in view of Agarwal et al. (US 2003/0104212 A1) as applied to claim 1, and further in view of Lutz et al. (US 8,088,245 B2, cited in IDS).
Regarding claim 5, Kramer in view of Agarwal renders obvious the liquid epoxy adhesive composition of claim 1 as explained above.
Kramer does not teach wherein the one or more carboxyl-terminated butadiene acrylonitrile (CTBN) is adducted with diglycidyl ether of bisphenol-F (DGEBF). However, Lutz teaches a reaction product of approximately 60% of a liquid diglycidyl ether of bisphenol F and 40% of a carboxy-terminated butadiene-acrylonitrile copolymer (12:32-36) that is present in a structural adhesive comprising a core-shell rubber, a liquid epoxy resin, an isocyanate-terminated polyurethane prepolymer in which the isocyanate groups are capped, and a curing agent that is cyanoguanidine15:45-16:13; 12:22-67). Kramer and Lutz are analogous art because both references are in the same field of endeavor of an epoxy adhesive composition comprising at least one epoxy resin, one or more carboxyl-terminated butadiene acrylonitrile copolymers (CTBN), rubber particles, one or more blocked polyurethane toughening agents, and at least one heat-activated latent curing agent comprising DICY. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Lutz’s reaction product of approximately 60% of a liquid diglycidyl ether of bisphenol F and 40% of a carboxy-terminated butadiene-acrylonitrile copolymer to substitute for Kramer’s 10.0 g of Polydis (D) that is bisphenol F diglycidyl ether, modified nitrile-butadiene rubber. The proposed modification would read on wherein the one or more carboxyl-terminated butadiene acrylonitrile (CTBN) is adducted with diglycidyl ether of bisphenol-F (DGEBF) as claimed. One of ordinary skill in the art would have been motivated to do so because Lutz teaches that the reaction product of approximately 60% of a liquid diglycidyl ether of bisphenol F and 40% of a carboxy-terminated butadiene-acrylonitrile copolymer (12:32-36) is beneficial for having reactive epoxide groups which can be cured further when a structural adhesive comprising the reaction product is cured (8:7-14) and is beneficial for being useful in a structural adhesive comprising a core-shell rubber, a liquid epoxy resin, an isocyanate-terminated polyurethane prepolymer in which the isocyanate groups are capped, and a curing agent that is cyanoguanidine15:45-16:13; 12:22-67), which would have been beneficial for modifying toughness and curing properties of Kramer’s heat-curing composition because Kramer teaches that the heat-curing composition comprises 10.0 g of Polydis (D) ([0179], TABLE 3, Composition 1) that is bisphenol F diglycidyl ether, modified nitrile-butadiene rubber ([0161], TABLE 1), that the (D) is a liquid rubber [0116, 0117, 0118, 0120, 0121, 0122], that the liquid rubber D is a carboxy- or epoxide-terminated polymer [0116], that the liquid rubber D is a carboxy- or epoxide-terminated acrylonitrile-butadiene copolymer, or a derivative thereof [0117], and that the Polydis is a liquid rubber D [0117], that liquid rubbers have a relatively long history of use as tougheners [0003], that the heat-curing composition comprises dicy (D) ([0179], TABLE 3, Composition 1) that is dicyandiamide ([0161], TABLE 1), and that the dicyandiamide is a hardener for epoxy resin [0108].
Claim 9 is rejected under 35 U.S.C. 103 as being unpatentable over Kramer et al. (US 2009/0264558 A1) in view of Agarwal et al. (US 2003/0104212 A1) as applied to claim 1, and further in view of Bank et al. (US 2018/0291164 A1).
Regarding claim 9, Kramer in view of Agarwal renders obvious the liquid epoxy adhesive composition of claim 1 as explained above. Kramer teaches that the composition further comprises at least one hardener B for epoxy resins [0108], that the materials here are preferably a hardener selected from dicyandiamide and substituted ureas [0108], that it is preferable that the hardener B involves a hardener selected from dicyandiamide, and substituted ureas [0109], which suggests using Kramer’s hardener B that is a hardener selected from substituted ureas to substitute for a fraction of Kramer’s 4.4 g of dicy (D) that is dicyandiamide, which would read on wherein the accelerator is a substituted urea as claimed.
Kramer does not teach a specific embodiment wherein the accelerator is or comprises urea, a guanidine, or a substituted urea. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Kramer’s hardener B that is a hardener selected from substituted ureas to substitute for a fraction of Kramer’s 4.4 g of dicy (D) that is dicyandiamide. The proposed modification would read on wherein the accelerator is a substituted urea as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying hardening properties of Kramer’s heat-curing composition at an elevated temperature because Kramer teaches that the heat-curing composition comprises 4.4 g of dicy (D) ([0179], TABLE 3, Composition 1) that is dicyandiamide ([0161], TABLE 1), that the composition further comprises at least one hardener B for epoxy resins, where this hardener is activated via an elevated temperature [0108], that the materials here are preferably a hardener selected from dicyandiamide and substituted ureas [0108], and that it is preferable that the hardener B involves a hardener selected from dicyandiamide, and substituted ureas [0109].
Kramer does not teach wherein the one or more dicyandiamide (DICY) comprises a micronized dicyandiamide, wherein d90 if the micronized dicyandiamide has a particle diameter of 40 microns or less. However, Bank teaches dicyandiamide particles having a particle distribution in which 98 percent of the dicyandiamide particles have a diameter less than 10 microns, and at least 35% of the dicyandiamide particles have a particle size of less than 2 microns that are a latent hardener that are present in an epoxy resin composition further comprising a first epoxy resin component, a second epoxy resin component, and an epoxy soluble latent catalyst [0008] that is a substituted urea [0012, 0019, 0070], wherein the composition is an adhesive composition [0182]. Kramer and Bank are analogous art because both references are in the same field of endeavor of an epoxy adhesive composition comprising at least one epoxy resin, at least one heat-activated latent curing agent comprising DICY, and at least one accelerator different from the curing agent that is a substituted urea. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Bank’s dicyandiamide particles having a particle distribution in which 98 percent of the dicyandiamide particles have a diameter less than 10 microns, and at least 35% of the dicyandiamide particles have a particle size of less than 2 microns to substitute for the remaining fraction of Kramer’s 4.4 g of dicy (D) that is dicyandiamide. The proposed modification would read on wherein the one or more dicyandiamide (DICY) comprises a micronized dicyandiamide, wherein d90 of the micronized dicyandiamide has a particle diameter of less than 10 microns as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying hardening properties of Kramer’s heat-curing composition at an elevated temperature because Bank teaches that the dicyandiamide particles having a particle distribution in which 98 percent of the dicyandiamide particles have a diameter less than 10 microns, and at least 35% of the dicyandiamide particles have a particle size of less than 2 microns are beneficial for being a latent hardener that is beneficial for being useful in an epoxy resin composition further comprising a first epoxy resin component, a second epoxy resin component, and an epoxy soluble latent catalyst [0008], and that the composition is beneficial for being useful as an adhesive composition [0182], and because Kramer teaches that the heat-curing composition comprises 4.4 g of dicy (D) ([0179], TABLE 3, Composition 1) that is dicyandiamide ([0161], TABLE 1), that the composition further comprises at least one hardener B for epoxy resins, where this hardener is activated via an elevated temperature [0108], that the materials here are preferably a hardener selected from dicyandiamide [0108], and that it is preferable that the hardener B involves a hardener selected from dicyandiamide [0109].
Claim 10 is rejected under 35 U.S.C. 103 as being unpatentable over Kramer et al. (US 2009/0264558 A1) in view of Agarwal et al. (US 2003/0104212 A1) as applied to claim 2, and further in view of Eagle et al. (US 9,346,983 B2, cited in IDS).
Regarding claim 10, Kramer in view of Agarwal renders obvious the liquid epoxy adhesive composition of claim 2 as explained above.
Kramer does not teach wherein the one or more flame retardant is present and comprises one or more of the claimed flame retardants. However, Eagle teaches a flame retardant mixture that includes alumina trihydrate, zinc borate, and melamine (1:62-64) that is present in a heat-curable structural adhesive further comprising at least one non-rubber-modified epoxy resin, one or more epoxy curing agents, and one or more epoxy curing catalysts (1:57-64). Kramer and Eagle are analogous art because both references are in the same field of endeavor of an epoxy adhesive composition comprising at least one epoxy resin, at least one heat-activated curing agent, and at least one accelerator different from the curing agent. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Eagle’s flame retardant mixture that includes alumina trihydrate, zinc borate, and melamine to modify Kramer’s heat-curing composition. The proposed modification would read on wherein the one or more flame retardant is present and comprises one or more of aluminum trihydrate (ATH), or melamine as claimed. One of ordinary skill in the art would have been motivated to do so because Eagle teaches that the flame retardant mixture that includes alumina trihydrate, zinc borate, and melamine is beneficial for being useful (1:62-64) in a heat-curable structural adhesive further comprising at least one non-rubber-modified epoxy resin, one or more epoxy curing agents, and one or more epoxy curing catalysts (1:57-64), and that the epoxy-based structural adhesive is beneficial for being flame-retardant (1:5-6), which would have been beneficial for improving flame retardant properties of Kramer’s heat-curing composition, which would have been desirable for Kramer’s heat-curing composition because Kramer teaches that the heat-curing epoxy resin composition is particularly suitable as a single-component adhesive, and that a particularly preferred application of the heat-curing epoxy resin composition is the adhesive bonding of identical or different metals in bodyshell construction in the automobile industry [0153], which would have required flame retarding properties to some extent.
Claim 12 is rejected under 35 U.S.C. 103 as being unpatentable over Kramer et al. (US 2009/0264558 A1) in view of Agarwal et al. (US 2003/0104212 A1) as applied to claim 1, and further in view of Antelmann et al. (US 2007/0027274 A1).
Regarding claim 12, Kramer in view of Agarwal renders obvious the liquid epoxy adhesive composition of claim 1 as explained above.
Kramer does not teach wherein the at least one accelerator different from the curing agent is or comprises a micronized urea-based accelerator, wherein the urea-based accelerator is urea, substituted urea having one, two, three, or four alkyl groups or a methylene bridged bis(phenylurea) N-substituted with one, two, three, or four alkyl groups, and/or wherein the accelerator becomes activated in a temperature range of 100°C to 180°C. However, Antelmann teaches an accelerator that is [0029] micronized 3-(3,4-dichlorophenyl)-1,1-dimethylurea [0030], micronized 3-phenyl-1,1-dimethylurea [0031], micronized toluylbis-1,1-dimethylurea [0032], N,N-dimeth