DETAILED ACTION
Applicant’s response filed on 02/09/2026, claims 1-11, 15-17, and 25 are canceled. Claims 12-14, 18-24, and 26-31 are pending. Claims 12, 18, 19, and 26 are 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. 17/049,361, filed on 10/21/2020.
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 12-14, 18-24, 26, and 28 are rejected under 35 U.S.C. 103 as being unpatentable over Zhang et al. (US 2016/0215142 A1) in view of Liu et al. (CN 101348563 A, machine translation in English used for citation).
Regarding claims 12-14, 18-20, 23, and 24, Zhang teaches preparing a phenalkamine compound by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082] in a round flask [0081, 0083], wherein the CNSL mainly comprises cardanol and cardol [0019], which read on a process for preparing a phenalkamine compound, the process comprising adding a first compound comprising one or more of a primary amine group and a secondary amine group, or a second compound comprising an ether group and one or more of a primary amine group and a secondary amine group, a cardanol, and a formaldehyde to a reaction vessel, reacting the cardanol with the first compound comprising one or more of a primary amine group and a secondary amine group, or the second compound comprising an ether group and one or more of a primary amine group and a secondary amine group in the presence of the formaldehyde, wherein the second compound comprises a polyether segment, wherein each of the first and second compounds comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group, wherein the first compound comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group, wherein the second compound comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group, wherein the formaldehyde is paraformaldehyde, wherein the second compound is polyetheramine, wherein the polyetheramine comprises a propylene oxide segment. Zhang teaches that the polyamine for preparing the phenalkamine compound can be aliphatic, cycloaliphatic, aromatic, polycyclic, polyamide, polyamidoamine, or mixtures thereof [0020], that examples of suitable aliphatic polyamines include diethylenetriamine (DETA) [0020], that examples of suitable polyoxyalkylene polyamines include JEFFAMINETM D-230 and JEFFAMINE D-400 polyoxypropylenediamines [0020], and that in some embodiments, the polyamines used are DETA, polyoxyproylenediamine, polyoxyethylenediamine, or mixtures thereof [0020], which suggests selecting a mixture of Zhang’s polyoxypropylenediamine and Zhang’s diethylenetriamine as Zhang’s polyamine that is reacted during preparing Zhang’s phenalkamine compound, which would read on the process comprising adding a first compound comprising one or more of a primary amine group and a secondary amine group, a second compound comprising an ether group and one or more of a primary amine group and a secondary amine group, a cardanol, and a formaldehyde to a reaction vessel, reacting the cardanol with the first compound comprising one or more of a primary amine group and a secondary amine group and the second compound comprising an ether group and one or more of a primary amine group and a secondary amine group in the presence of the formaldehyde as claimed, wherein the second compound comprises a polyether segment as claimed, wherein each of the first and second compounds comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group as claimed, wherein the first compound comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group as claimed, wherein the second compound comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group as claimed, wherein the formaldehyde is paraformaldehyde as claimed, wherein the second compound is polyetheramine as claimed, wherein the polyetheramine comprises a propylene oxide segment as claimed.
Zhang does not teach a specific embodiment of the process comprising adding a first compound comprising one or more of a primary amine group and a secondary amine group, and a second compound comprising an ether group and one or more of a primary amine group and a secondary amine group to a reaction vessel, reacting the one or more of a cardanol and a bisphenol with the first compound comprising one or more of a primary amine group and a secondary amine group and the second compound comprising an ether group and one or more of a primary amine group and a secondary amine group, wherein the second compound comprises a polyether segment, wherein each of the first and second compounds comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group, an aryl group, a heteroaryl group, a cycloalkyl group, or a heterocycloalkyl group, wherein the first compound comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group, an aryl group, a heteroaryl group, a cycloalkyl group, or a heterocycloalkyl group, wherein the second compound comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group, an aryl group, a heteroaryl group, a cycloalkyl group, or a heterocycloalkyl group, wherein the second compound is polyetheramine, wherein the polyetheramine comprises at least one of an oxyethylene diamine segment, an oxyethylene triamine segment, a polyoxyethylene diamine segment, a propylene oxide segment, or an ethylene oxide segment. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select a mixture of Zhang’s polyoxypropylenediamine and Zhang’s diethylenetriamine as Zhang’s polyamine that is reacted in Zhang’s round flask during preparing Zhang’s phenalkamine compound. The proposed modification would read on the process comprising adding a first compound comprising one or more of a primary amine group and a secondary amine group, a second compound comprising an ether group and one or more of a primary amine group and a secondary amine group, a cardanol, and a formaldehyde to a reaction vessel, reacting the cardanol with the first compound comprising one or more of a primary amine group and a secondary amine group and the second compound comprising an ether group and one or more of a primary amine group and a secondary amine group in the presence of the formaldehyde as claimed, wherein the second compound comprises a polyether segment as claimed, wherein each of the first and second compounds comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group as claimed, wherein the first compound comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group as claimed, wherein the second compound comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group as claimed, wherein the formaldehyde is paraformaldehyde as claimed, wherein the second compound is polyetheramine as claimed, wherein the polyetheramine comprises a propylene oxide segment as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying curing properties of Zhang’s phenalkamine compound because Zhang teaches that the phenalkamine compound is prepared by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082] in a round flask [0081, 0083], that the polyamine for preparing the phenalkamine compound can be aliphatic, cycloaliphatic, aromatic, polycyclic, polyamide, polyamidoamine, or mixtures thereof [0020], that examples of suitable aliphatic polyamines include diethylenetriamine (DETA) [0020], that examples of suitable polyoxyalkylene polyamines include JEFFAMINETM D-230 and JEFFAMINE D-400 polyoxypropylenediamines [0020], that in some embodiments, the polyamines used are DETA, polyoxyproylenediamine, polyoxyethylenediamine, or mixtures thereof [0020], and that the phenalkamine is a phenalkamine curing agent [0006].
Zhang does not teach that the process further comprises adding an acid catalyst to the reaction vessel, and that the reacting in the presence of a formaldehyde is further in the presence of the catalyst. However, Liu teaches an acidic catalyst that is used [0021] in a method for preparing a Mannich base curing agent comprising [0020] mixing tung oil and phenol and subjecting to Friedel-Crafts substitution reaction under the catalysis of the acid catalyst [0021], adding amines to the reaction system of the previous step to carry out a salt formation reaction, then adding aldehydes to the reaction system to carry out a Mannich reaction [0022], heating the product to complete the polycondensation reaction [0023], heating the crude curing agent obtained in the previous step, and distilling it under normal and reduced pressure to remove low-boiling substances and moisture from the reaction system [0024], wherein the phenols are phenol, o-cresol, mixed cresol, nonylphenol, p-tert-butylphenol, resorcinol, and bisphenol A [0013], wherein the aldehydes are optionally formaldehyde [0014], wherein the amines are one or more of ethylenediamine, hexamethylenediamine, diethylenetriamine, triethylenetetramine, polyethylene polyamine, m-phenylenediamine, m-phenylenediamine, isophorone diamine, and dimethylamine [0015]. Zhang and Liu are analogous art because both references are in the same field of endeavor of a process for preparing a Mannich base, the process comprising reacting a phenolic compound with a compound comprising one or more of a primary amine group and a secondary amine group in the presence of an aldehyde. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to carry out Zhang’s reacting CNSL, paraformaldehyde, and polyamines in the presence of Liu’s acidic catalyst in Zhang’s round flask. The proposed modification would read on the process further comprising adding an acid catalyst to the reaction vessel, and the reacting in the presence of a formaldehyde is further in the presence of the catalyst as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for catalyzing Zhang’s reacting CNSL, paraformaldehyde, and polyamines in Zhang’s round flask because Liu teaches an acidic catalyst that is used [0021] in a method for preparing a Mannich base curing agent comprising [0020] mixing tung oil and phenol and subjecting to Friedel-Crafts substitution reaction under the catalysis of the acid catalyst [0021], adding amines to the reaction system of the previous step to carry out a salt formation reaction, then adding aldehydes to the reaction system to carry out a Mannich reaction [0022], heating the product to complete the polycondensation reaction [0023], heating the crude curing agent obtained in the previous step, and distilling it under normal and reduced pressure to remove low-boiling substances and moisture from the reaction system [0024], wherein the phenols are phenol, o-cresol, mixed cresol, nonylphenol, p-tert-butylphenol, resorcinol, and bisphenol A [0013], wherein the aldehydes are optionally formaldehyde [0014], wherein the amines are one or more of ethylenediamine, hexamethylenediamine, diethylenetriamine, triethylenetetramine, polyethylene polyamine, m-phenylenediamine, m-phenylenediamine, isophorone diamine, and dimethylamine [0015], which is substantially similar to Zhang’s reacting CNSL, paraformaldehyde, and polyamines because Zhang teaches preparing a phenalkamine compound by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082] in a round flask [0081, 0083], wherein the CNSL mainly comprises cardanol and cardol [0019], that the polyamine for preparing the phenalkamine compound can be aliphatic, cycloaliphatic, aromatic, polycyclic, polyamide, polyamidoamine, or mixtures thereof [0020], that examples of suitable aliphatic polyamines include diethylenetriamine (DETA) [0020], that examples of suitable polyoxyalkylene polyamines include JEFFAMINETM D-230 and JEFFAMINE D-400 polyoxypropylenediamines [0020], and that in some embodiments, the polyamines used are DETA, polyoxyproylenediamine, polyoxyethylenediamine, or mixtures thereof [0020].
Regarding claim 21, Zhang in view of Liu satisfies the process of claim 12, wherein the bisphenol is Bisphenol A as claimed because claims 12 and 21 do not require the process to comprise adding a bisphenol to a reaction vessel, and reacting the bisphenol, if the process comprises adding a cardanol to a reaction vessel, and reacting the cardanol, and Zhang in view of Liu renders it obvious that the process comprises adding a cardanol to a reaction vessel, and reacting the cardanol, as explained above for claim 12.
Regarding claim 22, Zhang teaches preparing a phenalkamine compound by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082] in a round flask [0081, 0083], that the polyamine for preparing the phenalkamine compound can be aliphatic, cycloaliphatic, aromatic, polycyclic, polyamide, polyamidoamine, or mixtures thereof [0020], that examples of suitable aliphatic polyamines include diethylenetriamine (DETA) and triethylenetetramine (TETA) [0020], and that examples of suitable polyoxyalkylene polyamines include JEFFAMINETM D-230 and JEFFAMINE D-400 polyoxypropylenediamines [0020], which suggests using Zhang’s triethylenetetramine to substitute for Zhang’s diethylenetriamine, and selecting a mixture of Zhang’s polyoxypropylenediamine and Zhang’s triethylenetetramine as Zhang’s polyamine that is reacted during preparing Zhang’s phenalkamine compound, which would read on wherein the first compound is triethylenetetramine as claimed.
Zhang does not teach a specific embodiment wherein the first compound is triethylenetetramine. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Zhang’s triethylenetetramine to substitute for Zhang’s diethylenetriamine, and to select a mixture of Zhang’s polyoxypropylenediamine and Zhang’s triethylenetetramine as Zhang’s polyamine that is reacted in Zhang’s round flask during preparing Zhang’s phenalkamine compound. The proposed modification would read on wherein the first compound is triethylenetetramine as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying curing properties of Zhang’s phenalkamine compound because Zhang teaches that the phenalkamine compound is prepared by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082] in a round flask [0081, 0083], that the polyamine for preparing the phenalkamine compound can be aliphatic, cycloaliphatic, aromatic, polycyclic, polyamide, polyamidoamine, or mixtures thereof [0020], that examples of suitable aliphatic polyamines include diethylenetriamine (DETA) and triethylenetetramine (TETA) [0020], that examples of suitable polyoxyalkylene polyamines include JEFFAMINETM D-230 and JEFFAMINE D-400 polyoxypropylenediamines [0020], and that the phenalkamine is a phenalkamine curing agent [0006].
Regarding claim 26, Zhang does not teach that the acid is oxalic acid, a salt of oxalic acid, or a combination thereof. However, Liu teaches an acidic catalyst [0021] that is oxalic acid [0026] and that is used [0021] in a method for preparing a Mannich base curing agent comprising [0020] mixing tung oil and phenol and subjecting to Friedel-Crafts substitution reaction under the catalysis of the acid catalyst [0021], adding amines to the reaction system of the previous step to carry out a salt formation reaction, then adding aldehydes to the reaction system to carry out a Mannich reaction [0022], heating the product to complete the polycondensation reaction [0023], heating the crude curing agent obtained in the previous step, and distilling it under normal and reduced pressure to remove low-boiling substances and moisture from the reaction system [0024], wherein the phenols are phenol, o-cresol, mixed cresol, nonylphenol, p-tert-butylphenol, resorcinol, and bisphenol A [0013], wherein the aldehydes are optionally formaldehyde [0014], wherein the amines are one or more of ethylenediamine, hexamethylenediamine, diethylenetriamine, triethylenetetramine, polyethylene polyamine, m-phenylenediamine, m-phenylenediamine, isophorone diamine, and dimethylamine [0015]. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to carry out Zhang’s reacting CNSL, paraformaldehyde, and polyamines in the presence of Liu’s acidic catalyst that is oxalic acid in Zhang’s round flask. The proposed modification would read on wherein the acid is oxalic acid as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for catalyzing Zhang’s reacting CNSL, paraformaldehyde, and polyamines because Liu teaches an acidic catalyst [0021] that is oxalic acid [0026] and that is used [0021] in a method for preparing a Mannich base curing agent comprising [0020] mixing tung oil and phenol and subjecting to Friedel-Crafts substitution reaction under the catalysis of the acid catalyst [0021], adding amines to the reaction system of the previous step to carry out a salt formation reaction, then adding aldehydes to the reaction system to carry out a Mannich reaction [0022], heating the product to complete the polycondensation reaction [0023], heating the crude curing agent obtained in the previous step, and distilling it under normal and reduced pressure to remove low-boiling substances and moisture from the reaction system [0024], wherein the phenols are phenol, o-cresol, mixed cresol, nonylphenol, p-tert-butylphenol, resorcinol, and bisphenol A [0013], wherein the aldehydes are optionally formaldehyde [0014], wherein the amines are one or more of ethylenediamine, hexamethylenediamine, diethylenetriamine, triethylenetetramine, polyethylene polyamine, m-phenylenediamine, m-phenylenediamine, isophorone diamine, and dimethylamine [0015], which is substantially similar to Zhang’s reacting CNSL, paraformaldehyde, and polyamines because Zhang teaches preparing a phenalkamine compound by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082] in a round flask [0081, 0083], wherein the CNSL mainly comprises cardanol and cardol [0019], that the polyamine for preparing the phenalkamine compound can be aliphatic, cycloaliphatic, aromatic, polycyclic, polyamide, polyamidoamine, or mixtures thereof [0020], that examples of suitable aliphatic polyamines include diethylenetriamine (DETA) [0020], that examples of suitable polyoxyalkylene polyamines include JEFFAMINETM D-230 and JEFFAMINE D-400 polyoxypropylenediamines [0020], and that in some embodiments, the polyamines used are DETA, polyoxyproylenediamine, polyoxyethylenediamine, or mixtures thereof [0020].
Regarding claim 28, Zhang teaches a curable asphalt composition comprising pigments [0048], and an asphalt emulsion comprising asphalt, the phenalkamine compound, an emulsifier, an acid, water [0008], and a waterborne epoxy resin [0009], which reads on the process of claim 12, further comprising adding a coloring agent as claimed.
Claims 12-14, 18-24, and 28 are rejected under 35 U.S.C. 103 as being unpatentable over Zhang et al. (US 2016/0215142 A1) in view of Zhong et al. (CN 103881773 A, machine translation in English used for citation).
Regarding claims 12-14, 18-20, 23, and 24, Zhang teaches preparing a phenalkamine compound by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082] in a round flask [0081, 0083], wherein the CNSL mainly comprises cardanol and cardol [0019], which read on a process for preparing a phenalkamine compound, the process comprising adding a first compound comprising one or more of a primary amine group and a secondary amine group, or a second compound comprising an ether group and one or more of a primary amine group and a secondary amine group, a cardanol, and a formaldehyde to a reaction vessel, reacting the cardanol with the first compound comprising one or more of a primary amine group and a secondary amine group, or the second compound comprising an ether group and one or more of a primary amine group and a secondary amine group in the presence of the formaldehyde, wherein the second compound comprises a polyether segment, wherein each of the first and second compounds comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group, wherein the first compound comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group, wherein the second compound comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group, wherein the formaldehyde is paraformaldehyde, wherein the second compound is polyetheramine, wherein the polyetheramine comprises a propylene oxide segment. Zhang teaches that the polyamine for preparing the phenalkamine compound can be aliphatic, cycloaliphatic, aromatic, polycyclic, polyamide, polyamidoamine, or mixtures thereof [0020], that examples of suitable aliphatic polyamines include diethylenetriamine (DETA) [0020], that examples of suitable polyoxyalkylene polyamines include JEFFAMINETM D-230 and JEFFAMINE D-400 polyoxypropylenediamines [0020], and that in some embodiments, the polyamines used are DETA, polyoxyproylenediamine, polyoxyethylenediamine, or mixtures thereof [0020], which suggests selecting a mixture of Zhang’s polyoxypropylenediamine and Zhang’s diethylenetriamine as Zhang’s polyamine that is reacted during preparing Zhang’s phenalkamine compound, which would read on the process comprising adding a first compound comprising one or more of a primary amine group and a secondary amine group, a second compound comprising an ether group and one or more of a primary amine group and a secondary amine group, a cardanol, and a formaldehyde to a reaction vessel, reacting the cardanol with the first compound comprising one or more of a primary amine group and a secondary amine group and the second compound comprising an ether group and one or more of a primary amine group and a secondary amine group in the presence of the formaldehyde as claimed, wherein the second compound comprises a polyether segment as claimed, wherein each of the first and second compounds comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group as claimed, wherein the first compound comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group as claimed, wherein the second compound comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group as claimed, wherein the formaldehyde is paraformaldehyde as claimed, wherein the second compound is polyetheramine as claimed, wherein the polyetheramine comprises a propylene oxide segment as claimed.
Zhang does not teach a specific embodiment of the process comprising adding a first compound comprising one or more of a primary amine group and a secondary amine group, and a second compound comprising an ether group and one or more of a primary amine group and a secondary amine group to a reaction vessel, reacting the one or more of a cardanol and a bisphenol with the first compound comprising one or more of a primary amine group and a secondary amine group and the second compound comprising an ether group and one or more of a primary amine group and a secondary amine group, wherein the second compound comprises a polyether segment, wherein each of the first and second compounds comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group, an aryl group, a heteroaryl group, a cycloalkyl group, or a heterocycloalkyl group, wherein the first compound comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group, an aryl group, a heteroaryl group, a cycloalkyl group, or a heterocycloalkyl group, wherein the second compound comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group, an aryl group, a heteroaryl group, a cycloalkyl group, or a heterocycloalkyl group, wherein the second compound is polyetheramine, wherein the polyetheramine comprises at least one of an oxyethylene diamine segment, an oxyethylene triamine segment, a polyoxyethylene diamine segment, a propylene oxide segment, or an ethylene oxide segment. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select a mixture of Zhang’s polyoxypropylenediamine and Zhang’s diethylenetriamine as Zhang’s polyamine that is reacted in Zhang’s round flask during preparing Zhang’s phenalkamine compound. The proposed modification would read on the process comprising adding a first compound comprising one or more of a primary amine group and a secondary amine group, a second compound comprising an ether group and one or more of a primary amine group and a secondary amine group, a cardanol, and a formaldehyde to a reaction vessel, reacting the cardanol with the first compound comprising one or more of a primary amine group and a secondary amine group and the second compound comprising an ether group and one or more of a primary amine group and a secondary amine group in the presence of the formaldehyde as claimed, wherein the second compound comprises a polyether segment as claimed, wherein each of the first and second compounds comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group as claimed, wherein the first compound comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group as claimed, wherein the second compound comprising one or more of a primary amine group and a secondary amine group further comprises an alkyl group as claimed, wherein the formaldehyde is paraformaldehyde as claimed, wherein the second compound is polyetheramine as claimed, wherein the polyetheramine comprises a propylene oxide segment as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying curing properties of Zhang’s phenalkamine compound because Zhang teaches that the phenalkamine compound is prepared by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082] in a round flask [0081, 0083], that the polyamine for preparing the phenalkamine compound can be aliphatic, cycloaliphatic, aromatic, polycyclic, polyamide, polyamidoamine, or mixtures thereof [0020], that examples of suitable aliphatic polyamines include diethylenetriamine (DETA) [0020], that examples of suitable polyoxyalkylene polyamines include JEFFAMINETM D-230 and JEFFAMINE D-400 polyoxypropylenediamines [0020], that in some embodiments, the polyamines used are DETA, polyoxyproylenediamine, polyoxyethylenediamine, or mixtures thereof [0020], and that the phenalkamine is a phenalkamine curing agent [0006].
Zhang does not teach that the process further comprises adding an acid catalyst to the reaction vessel, and that the reacting in the presence of a formaldehyde is further in the presence of the catalyst. However, Zhong teaches acid catalyst that is used [0009] in a preparation method of phenolic amine type Mannich base occlusive agents comprising [0008] adding an alcohol-water solvent, formalin solution, and alkylamine, along with a few drops of the acid catalyst to a reaction vessel 1, adding phenol to a reaction vessel 2 and dissolving it in an alcohol-water solvent, adding the solution from reaction vessel 1 to reaction vessel 2, reacting, and obtaining phenol-aldehyde-amine type Mannich base compound [0009], wherein the phenol can be phenol or o-cresol [0017], wherein the alkylamine is dimethylamine, diethylamine, or diethanolamine [0018]. Zhang and Zhong are analogous art because both references are in the same field of endeavor of a process for preparing a Mannich base, the process comprising reacting a phenolic compound with a compound comprising a secondary amine group in the presence of an aldehyde. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to carry out Zhang’s reacting CNSL, paraformaldehyde, and polyamines in the presence of Zhong’s acid catalyst in Zhang’s round flask. The proposed modification would read on the process further comprising adding an acid catalyst to the reaction vessel, and the reacting in the presence of a formaldehyde is further in the presence of the catalyst as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for catalyzing Zhang’s reacting CNSL, paraformaldehyde, and polyamines in Zhang’s round flask because Zhong teaches acid catalyst that is used [0009] in a preparation method of phenolic amine type Mannich base occlusive agents comprising [0008] adding an alcohol-water solvent, formalin solution, and alkylamine, along with a few drops of the acid catalyst to a reaction vessel 1, adding phenol to a reaction vessel 2 and dissolving it in an alcohol-water solvent, adding the solution from reaction vessel 1 to reaction vessel 2, reacting, and obtaining phenol-aldehyde-amine type Mannich base compound [0009], wherein the phenol can be phenol or o-cresol [0017], wherein the alkylamine is dimethylamine, diethylamine, or diethanolamine [0018], which is substantially similar to Zhang’s reacting CNSL, paraformaldehyde, and polyamines because Zhang teaches preparing a phenalkamine compound by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082] in a round flask [0081, 0083], wherein the CNSL mainly comprises cardanol and cardol [0019], that the polyamine for preparing the phenalkamine compound can be aliphatic, cycloaliphatic, aromatic, polycyclic, polyamide, polyamidoamine, or mixtures thereof [0020], that examples of suitable aliphatic polyamines include diethylenetriamine (DETA) [0020], that examples of suitable polyoxyalkylene polyamines include JEFFAMINETM D-230 and JEFFAMINE D-400 polyoxypropylenediamines [0020], and that in some embodiments, the polyamines used are DETA, polyoxyproylenediamine, polyoxyethylenediamine, or mixtures thereof [0020].
Regarding claim 21, Zhang in view of Zhong satisfies the process of claim 12, wherein the bisphenol is Bisphenol A as claimed because claims 12 and 21 do not require the process to comprise adding a bisphenol to a reaction vessel, and reacting the bisphenol, if the process comprises adding a cardanol to a reaction vessel, and reacting the cardanol, and Zhang in view of Zhong renders it obvious that the process comprises adding a cardanol to a reaction vessel, and reacting the cardanol, as explained above for claim 12.
Regarding claim 22, Zhang teaches preparing a phenalkamine compound by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082] in a round flask [0081, 0083], that the polyamine for preparing the phenalkamine compound can be aliphatic, cycloaliphatic, aromatic, polycyclic, polyamide, polyamidoamine, or mixtures thereof [0020], that examples of suitable aliphatic polyamines include diethylenetriamine (DETA) and triethylenetetramine (TETA) [0020], and that examples of suitable polyoxyalkylene polyamines include JEFFAMINETM D-230 and JEFFAMINE D-400 polyoxypropylenediamines [0020], which suggests using Zhang’s triethylenetetramine to substitute for Zhang’s diethylenetriamine, and selecting a mixture of Zhang’s polyoxypropylenediamine and Zhang’s triethylenetetramine as Zhang’s polyamine that is reacted during preparing Zhang’s phenalkamine compound, which would read on wherein the first compound is triethylenetetramine as claimed.
Zhang does not teach a specific embodiment wherein the first compound is triethylenetetramine. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Zhang’s triethylenetetramine to substitute for Zhang’s diethylenetriamine, and to select a mixture of Zhang’s polyoxypropylenediamine and Zhang’s triethylenetetramine as Zhang’s polyamine that is reacted in Zhang’s round flask during preparing Zhang’s phenalkamine compound. The proposed modification would read on wherein the first compound is triethylenetetramine as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying curing properties of Zhang’s phenalkamine compound because Zhang teaches that the phenalkamine compound is prepared by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082] in a round flask [0081, 0083], that the polyamine for preparing the phenalkamine compound can be aliphatic, cycloaliphatic, aromatic, polycyclic, polyamide, polyamidoamine, or mixtures thereof [0020], that examples of suitable aliphatic polyamines include diethylenetriamine (DETA) and triethylenetetramine (TETA) [0020], that examples of suitable polyoxyalkylene polyamines include JEFFAMINETM D-230 and JEFFAMINE D-400 polyoxypropylenediamines [0020], and that the phenalkamine is a phenalkamine curing agent [0006].
Regarding claim 28, Zhang teaches a curable asphalt composition comprising pigments [0048], and an asphalt emulsion comprising asphalt, the phenalkamine compound, an emulsifier, an acid, water [0008], and a waterborne epoxy resin [0009], which reads on the process of claim 12, further comprising adding a coloring agent as claimed.
Claim 27 is rejected under 35 U.S.C. 103 as being unpatentable over Zhang et al. (US 2016/0215142 A1) in view of Liu et al. (CN 101348563 A, machine translation in English used for citation) as applied to claim 12, and further in view of Zheng et al. (US 2017/0240691 A1).
Regarding claim 27, Zhang in view of Liu renders obvious the process of claim 12. Zhang teaches that water generated during reaction is removed by xylene under azeotropic distillation [0081, 0083], which reads on the process of claim 12, further comprising removing residual water from the compound.
Zhang does not teach that the process of claim 12 further comprises removing residual water from the compound by applying a vacuum. However, Zheng teaches subjection a reaction to vacuum distillation to remove all water, wherein the reaction is synthesis of Mannich base of cardanol with dimethylamine by reacting cardanol, dimethyl amine, and formaldehyde [0148]. Zhang and Zheng are analogous art because both references are in the same field of endeavor of a process for preparing a phenalkamine compound comprising in the presence of a formaldehyde, reacting a cardanol with a compound comprising a second amine group. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to remove water generated during Zhang’s reaction by subjecting the product of Zhang’s reaction to vacuum distillation, as suggested by Zheng. The proposed modification would read on the process of claim 12, further comprising removing residual water from the compound by applying a vacuum as claimed. One of ordinary skill in the art would have been motivated to do so because Zheng teaches that subjecting a reaction to vacuum distillation is beneficial for removing all water, wherein the reaction is synthesis of Mannich base of cardanol with dimethylamine by reacting cardanol, dimethyl amine, and formaldehyde [0148], which is substantially similar to Zhang’s reaction because Zhang teaches preparing a phenalkamine compound by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082], wherein the CNSL mainly comprises cardanol and cardol [0019], which means that the proposed modification would have been beneficial for removing substantially all water generated during Zhang’s reaction, which would have been desirable because Zhang teaches that water generated during reaction is removed by xylene under azeotropic distillation [0081, 0083].
Claim 27 is rejected under 35 U.S.C. 103 as being unpatentable over Zhang et al. (US 2016/0215142 A1) in view of Zhong et al. (CN 103881773 A, machine translation in English used for citation) as applied to claim 12, and further in view of Zheng et al. (US 2017/0240691 A1).
Regarding claim 27, Zhang in view of Zhong renders obvious the process of claim 12. Zhang teaches that water generated during reaction is removed by xylene under azeotropic distillation [0081, 0083], which reads on the process of claim 12, further comprising removing residual water from the compound.
Zhang does not teach that the process of claim 12 further comprises removing residual water from the compound by applying a vacuum. However, Zheng teaches subjection a reaction to vacuum distillation to remove all water, wherein the reaction is synthesis of Mannich base of cardanol with dimethylamine by reacting cardanol, dimethyl amine, and formaldehyde [0148]. Zhang and Zheng are analogous art because both references are in the same field of endeavor of a process for preparing a phenalkamine compound comprising in the presence of a formaldehyde, reacting a cardanol with a compound comprising a second amine group. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to remove water generated during Zhang’s reaction by subjecting the product of Zhang’s reaction to vacuum distillation, as suggested by Zheng. The proposed modification would read on the process of claim 12, further comprising removing residual water from the compound by applying a vacuum as claimed. One of ordinary skill in the art would have been motivated to do so because Zheng teaches that subjecting a reaction to vacuum distillation is beneficial for removing all water, wherein the reaction is synthesis of Mannich base of cardanol with dimethylamine by reacting cardanol, dimethyl amine, and formaldehyde [0148], which is substantially similar to Zhang’s reaction because Zhang teaches preparing a phenalkamine compound by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082], wherein the CNSL mainly comprises cardanol and cardol [0019], which means that the proposed modification would have been beneficial for removing substantially all water generated during Zhang’s reaction, which would have been desirable because Zhang teaches that water generated during reaction is removed by xylene under azeotropic distillation [0081, 0083].
Claim 29-31 are rejected under 35 U.S.C. 103 as being unpatentable over Zhang et al. (US 2016/0215142 A1) in view of Liu et al. (CN 101348563 A, machine translation in English used for citation) and Zheng et al. (US 2017/0240691 A1).
Regarding claim 29, Zhang teaches preparing a phenalkamine compound by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082], wherein the CNSL mainly comprises cardanol and cardol [0019], wherein the phenalkamine compound is a curing agent [0006], wherein formaldehyde is optionally used instead of the paraformaldehyde [0020], wherein the polyamine for preparing the phenalkamine compound can be aliphatic, cycloaliphatic, aromatic, polycyclic, polyamide, polyamidoamine, or mixtures thereof [0020], wherein examples of suitable aliphatic polyamines include diethylenetriamine (DETA) and triethylenetetramine (TETA) [0020], wherein examples of suitable polyoxyalkylene polyamines include JEFFAMINETM D-230 and JEFFAMINE D-400 polyoxypropylenediamines [0020], which suggests using Zhang’’s formaldehyde to substitute of Zhang’s paraformaldehyde, and selecting a mixture of Zhang’s polyoxypropylenediamine and Zhang’s triethylenetetramine as Zhang’s polyamine that is reacted during preparing Zhang’s phenalkamine compound, which would read on a process for preparing a curing agent, the process comprising in the presence of formaldehyde, reacting a cardanol with triethylenetetramine and a polyetheramine.
Zhang does not teach a specific embodiment of the process comprising in the presence of formaldehyde, reacting a cardanol with triethylenetetramine and a polyetheramine. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Zhang’’s formaldehyde to substitute of Zhang’s paraformaldehyde, to use Zhang’s triethylenetetramine to substitute for Zhang’s diethylenetriamine, and to select a mixture of Zhang’s polyoxypropylenediamine and Zhang’s triethylenetetramine as Zhang’s polyamine that is reacted during preparing Zhang’s phenalkamine compound. The proposed modification would read on the process comprising in the presence of formaldehyde, reacting a cardanol with triethylenetetramine and a polyetheramine as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying curing properties of Zhang’s phenalkamine compound because Zhang teaches that the phenalkamine compound is prepared by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082], that formaldehyde is optionally used instead of the paraformaldehyde [0020], that the polyamine for preparing the phenalkamine compound can be aliphatic, cycloaliphatic, aromatic, polycyclic, polyamide, polyamidoamine, or mixtures thereof [0020], that examples of suitable aliphatic polyamines include diethylenetriamine (DETA) and triethylenetetramine (TETA) [0020], that examples of suitable polyoxyalkylene polyamines include JEFFAMINETM D-230 and JEFFAMINE D-400 polyoxypropylenediamines [0020], and that the phenalkamine is a phenalkamine curing agent [0006].
Zhang does not teach that the process comprises further in the presence of oxalic acid, reacting the cardanol. However, Liu teaches an acidic catalyst [0021] that is oxalic acid [0026] and that is used [0021] in a method for preparing a Mannich base curing agent comprising [0020] mixing tung oil and phenol and subjecting to Friedel-Crafts substitution reaction under the catalysis of the acid catalyst [0021], adding amines to the reaction system of the previous step to carry out a salt formation reaction, then adding aldehydes to the reaction system to carry out a Mannich reaction [0022], heating the product to complete the polycondensation reaction [0023], heating the crude curing agent obtained in the previous step, and distilling it under normal and reduced pressure to remove low-boiling substances and moisture from the reaction system [0024], wherein the phenols are phenol, o-cresol, mixed cresol, nonylphenol, p-tert-butylphenol, resorcinol, and bisphenol A [0013], wherein the aldehydes are optionally formaldehyde [0014], wherein the amines are one or more of ethylenediamine, hexamethylenediamine, diethylenetriamine, triethylenetetramine, polyethylene polyamine, m-phenylenediamine, m-phenylenediamine, isophorone diamine, and dimethylamine [0015]. Zhang and Liu are analogous art because both references are in the same field of endeavor of a process for preparing a Mannich base, the process comprising in the presence of an aldehyde, reacting a phenolic compound with a compound comprising one or more of a primary amine group and a secondary amine group. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to carry out Zhang’s reacting in the presence of Liu’s acidic catalyst that is oxalic acid. The proposed modification would read on the process comprises further in the presence of oxalic acid, reacting the cardanol as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for catalyzing Zhang’s reacting CNSL, formaldehyde, and polyamines because Liu teaches an acidic catalyst [0021] that is oxalic acid [0026] and that is used [0021] in a method for preparing a Mannich base curing agent comprising [0020] mixing tung oil and phenol and subjecting to Friedel-Crafts substitution reaction under the catalysis of the acid catalyst [0021], adding amines to the reaction system of the previous step to carry out a salt formation reaction, then adding aldehydes to the reaction system to carry out a Mannich reaction [0022], heating the product to complete the polycondensation reaction [0023], heating the crude curing agent obtained in the previous step, and distilling it under normal and reduced pressure to remove low-boiling substances and moisture from the reaction system [0024], wherein the phenols are phenol, o-cresol, mixed cresol, nonylphenol, p-tert-butylphenol, resorcinol, and bisphenol A [0013], wherein the aldehydes are optionally formaldehyde [0014], wherein the amines are one or more of ethylenediamine, hexamethylenediamine, diethylenetriamine, triethylenetetramine, polyethylene polyamine, m-phenylenediamine, m-phenylenediamine, isophorone diamine, and dimethylamine [0015], which is substantially similar to Zhang’s reacting CNSL, paraformaldehyde, and polyamines because Zhang teaches preparing a phenalkamine compound by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082], that the CNSL mainly comprises cardanol and cardol [0019], that formaldehyde is optionally used instead of the paraformaldehyde [0020], that formaldehyde is optionally used instead of the paraformaldehyde [0020], that the polyamine for preparing the phenalkamine compound can be aliphatic, cycloaliphatic, aromatic, polycyclic, polyamide, polyamidoamine, or mixtures thereof [0020], that examples of suitable aliphatic polyamines include diethylenetriamine (DETA) and triethylenetetramine (TETA) [0020], and that examples of suitable polyoxyalkylene polyamines include JEFFAMINETM D-230 and JEFFAMINE D-400 polyoxypropylenediamines [0020].
Zhang does not teach that the process comprises further reacting a bisphenol with the triethylenetetramine and the polyetheramine. However, Zheng teaches obtaining a substituted phenolic compound, also known as Mannich bases, by reacting a phenolic compound with formaldehyde and an appropriate amine [0049], wherein the substituted phenolic compound is a low molecular weight di-alkylaminomethyl-substituted cardanol, 4,4′-dihydroxydiphenyl ether, 4,4′-dihydroxydiphenylsulfone, 4,4′-dihydroxydiphenylmethane, or bisphenol A [0046], wherein the amine is selected from a primary or a secondary amine [0049]. Zhang and Zheng are analogous art because both references are in the same field of endeavor of a process for preparing a Mannich base, the process comprising in the presence of an aldehyde, reacting a phenolic compound with a compound comprising one or more of a primary amine group and a secondary amine group. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Zheng’s 4,4′-dihydroxydiphenyl ether, 4,4′-dihydroxydiphenylsulfone, 4,4′-dihydroxydiphenylmethane, or bisphenol A to substitute for a fraction of Zhang’s CNSL that is reacted to prepare Zhang’s phenalkamine compound. The proposed modification would read on the process comprises further reacting a bisphenol with the triethylenetetramine and the polyetheramine as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying curing properties of Zhang’s phenalkamine compound because Zheng teaches that the 4,4′-dihydroxydiphenyl ether, 4,4′-dihydroxydiphenylsulfone, 4,4′-dihydroxydiphenylmethane, or bisphenol A is a phenolic compound [0046] that is beneficial for reacting with formaldehyde and an appropriate amine to obtain a substituted phenolic compound, also known as Mannich bases [0049], wherein the amine is selected from a primary or a secondary amine [0049], wherein the phenolic compound is optionally cardanol instead of the 4,4′-dihydroxydiphenyl ether, 4,4′-dihydroxydiphenylsulfone, 4,4′-dihydroxydiphenylmethane, or bisphenol A [0046], which is substantially similar to Zhang’s reacting CNSL, paraformaldehyde, and polyamines because Zhang teaches preparing a phenalkamine compound by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082], that the CNSL mainly comprises cardanol and cardol [0019], that formaldehyde is optionally used instead of the paraformaldehyde [0020], that formaldehyde is optionally used instead of the paraformaldehyde [0020], that the polyamine for preparing the phenalkamine compound can be aliphatic, cycloaliphatic, aromatic, polycyclic, polyamide, polyamidoamine, or mixtures thereof [0020], that examples of suitable aliphatic polyamines include diethylenetriamine (DETA) and triethylenetetramine (TETA) [0020], and that examples of suitable polyoxyalkylene polyamines include JEFFAMINETM D-230 and JEFFAMINE D-400 polyoxypropylenediamines [0020].
Regarding claim 30, Zhang teaches that water generated during reaction is removed by xylene under azeotropic distillation [0081, 0083], which reads on the process of claim 29 further comprising removing residual water from the curing agent.
Zhang does not teach that the process of claim 29 further comprises removing residual water from the curing agent by applying a vacuum. However, Zheng teaches subjection a reaction to vacuum distillation to remove all water, wherein the reaction is synthesis of Mannich base of cardanol with dimethylamine by reacting cardanol, dimethyl amine, and formaldehyde [0148]. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to remove water generated during Zhang’s reaction by subjecting the product of Zhang’s reaction to vacuum distillation, as suggested by Zheng. The proposed modification would read on the process of claim 29 further comprising removing residual water from the curing agent by applying a vacuum as claimed.
Regarding claim 31, Zhang teaches preparing a phenalkamine compound by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082], wherein the CNSL mainly comprises cardanol and cardol [0019].
Zhang does not teach that the cardanol and the bisphenol are present in about a 50:50 ratio. However, Zheng teaches obtaining a substituted phenolic compound, also known as Mannich bases, by reacting a phenolic compound with formaldehyde and an appropriate amine [0049], wherein the substituted phenolic compound is a low molecular weight di-alkylaminomethyl-substituted cardanol, 4,4′-dihydroxydiphenyl ether, 4,4′-dihydroxydiphenylsulfone, 4,4′-dihydroxydiphenylmethane, or bisphenol A [0046], wherein the amine is selected from a primary or a secondary amine [0049]. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Zheng’s 4,4′-dihydroxydiphenyl ether, 4,4′-dihydroxydiphenylsulfone, 4,4′-dihydroxydiphenylmethane, or bisphenol A to substitute for a fraction of Zhang’s cardanol in Zhang’s CNSL that is reacted to prepare Zhang’s phenalkamine compound, such that the amount of Zhang’s cardanol is about equal to the amount of Zheng’s 4,4′-dihydroxydiphenyl ether, 4,4′-dihydroxydiphenylsulfone, 4,4′-dihydroxydiphenylmethane, or bisphenol A. The proposed modification would read on wherein the cardanol and the bisphenol are present in about a 50:50 ratio as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying curing properties of Zhang’s phenalkamine compound because Zheng teaches that the 4,4′-dihydroxydiphenyl ether, 4,4′-dihydroxydiphenylsulfone, 4,4′-dihydroxydiphenylmethane, or bisphenol A is a phenolic compound [0046] that is beneficial for reacting with formaldehyde and an appropriate amine to obtain a substituted phenolic compound, also known as Mannich bases [0049], wherein the amine is selected from a primary or a secondary amine [0049], wherein the phenolic compound is optionally cardanol instead of the 4,4′-dihydroxydiphenyl ether, 4,4′-dihydroxydiphenylsulfone, 4,4′-dihydroxydiphenylmethane, or bisphenol A [0046], which is substantially similar to Zhang’s reacting CNSL, paraformaldehyde, and polyamines because Zhang teaches preparing a phenalkamine compound by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082], that the CNSL mainly comprises cardanol and cardol [0019], that formaldehyde is optionally used instead of the paraformaldehyde [0020], that formaldehyde is optionally used instead of the paraformaldehyde [0020], that the polyamine for preparing the phenalkamine compound can be aliphatic, cycloaliphatic, aromatic, polycyclic, polyamide, polyamidoamine, or mixtures thereof [0020], that examples of suitable aliphatic polyamines include diethylenetriamine (DETA) and triethylenetetramine (TETA) [0020], and that examples of suitable polyoxyalkylene polyamines include JEFFAMINETM D-230 and JEFFAMINE D-400 polyoxypropylenediamines [0020].
Response to Arguments
Applicant’s arguments, see p. 4, filed 02/09/2026, with respect to the objection to claims 18 and 19 have been fully considered and are persuasive. The objection to claims 18 and 19 has been withdrawn.
Applicant's arguments filed 02/09/2026 have been fully considered but they are not persuasive. In response to the applicant’s argument that the Examiner contends that one of ordinary skill in the art would have been motivated to use a combination of an ether containing amine and an amine that is not required to have an ether group because Zhang teaches these types of amines individually (p. 4), the Office actually contends that one of ordinary skill in the art would have been motivated to select a mixture of Zhang’s polyoxypropylenediamine and Zhang’s diethylenetriamine as Zhang’s polyamine that is reacted in Zhang’s round flask during preparing Zhang’s phenalkamine compound because it would have been beneficial for modifying curing properties of Zhang’s phenalkamine compound because Zhang teaches that the phenalkamine compound is prepared by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082] in a round flask [0081, 0083], that the polyamine for preparing the phenalkamine compound can be aliphatic, cycloaliphatic, aromatic, polycyclic, polyamide, polyamidoamine, or mixtures thereof [0020], that examples of suitable aliphatic polyamines include diethylenetriamine (DETA) [0020], that examples of suitable polyoxyalkylene polyamines include JEFFAMINETM D-230 and JEFFAMINE D-400 polyoxypropylenediamines [0020], that in some embodiments, the polyamines used are DETA, polyoxyproylenediamine, polyoxyethylenediamine, or mixtures thereof [0020], and that the phenalkamine is a phenalkamine curing agent [0006].
In response to the applicant’s argument that Liu does not teach a one step reaction as described in the pending claims (p. 4), the rejection of the claims that is set forth in this Office action does not rely on Liu for a teaching or suggestion of the claimed one step reaction and is not based on Liu individually. The rejection of claim 12 relies on Zhang for rendering it obvious that the process comprises adding a first compound comprising one or more of a primary amine group and a secondary amine group, a second compound comprising an ether group and one or more of a primary amine group and a secondary amine group, a cardanol, and a formaldehyde to a reaction vessel, reacting the cardanol with the first compound comprising one or more of a primary amine group and a secondary amine group and the second compound comprising an ether group and one or more of a primary amine group and a secondary amine group in the presence of the formaldehyde as claimed. The rejection of the claim 12 relies on Liu for a teaching and/or suggestion to carry out Zhang’s reacting CNSL, paraformaldehyde, and polyamines in the presence of Liu’s acidic catalyst in Zhang’s round flask. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to carry out Zhang’s reacting CNSL, paraformaldehyde, and polyamines in the presence of Liu’s acidic catalyst in Zhang’s round flask. The proposed modification would read on the process further comprising adding an acid catalyst to the reaction vessel, and the reacting in the presence of a formaldehyde is further in the presence of the catalyst as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for catalyzing Zhang’s reacting CNSL, paraformaldehyde, and polyamines in Zhang’s round flask because Liu teaches an acidic catalyst that is used [0021] in a method for preparing a Mannich base curing agent comprising [0020] mixing tung oil and phenol and subjecting to Friedel-Crafts substitution reaction under the catalysis of the acid catalyst [0021], adding amines to the reaction system of the previous step to carry out a salt formation reaction, then adding aldehydes to the reaction system to carry out a Mannich reaction [0022], heating the product to complete the polycondensation reaction [0023], heating the crude curing agent obtained in the previous step, and distilling it under normal and reduced pressure to remove low-boiling substances and moisture from the reaction system [0024], wherein the phenols are phenol, o-cresol, mixed cresol, nonylphenol, p-tert-butylphenol, resorcinol, and bisphenol A [0013], wherein the aldehydes are optionally formaldehyde [0014], wherein the amines are one or more of ethylenediamine, hexamethylenediamine, diethylenetriamine, triethylenetetramine, polyethylene polyamine, m-phenylenediamine, m-phenylenediamine, isophorone diamine, and dimethylamine [0015], which is substantially similar to Zhang’s reacting CNSL, paraformaldehyde, and polyamines because Zhang teaches preparing a phenalkamine compound by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082] in a round flask [0081, 0083], wherein the CNSL mainly comprises cardanol and cardol [0019], that the polyamine for preparing the phenalkamine compound can be aliphatic, cycloaliphatic, aromatic, polycyclic, polyamide, polyamidoamine, or mixtures thereof [0020], that examples of suitable aliphatic polyamines include diethylenetriamine (DETA) [0020], that examples of suitable polyoxyalkylene polyamines include JEFFAMINETM D-230 and JEFFAMINE D-400 polyoxypropylenediamines [0020], and that in some embodiments, the polyamines used are DETA, polyoxyproylenediamine, polyoxyethylenediamine, or mixtures thereof [0020]. One cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).
In response to the applicant’s argument that because the combination of Zhang and Liu does not teach all the elements of the claims, Zhang and Liu cannot provide sufficient basis for a case of obviousness (p. 5), Zhang in view of Liu renders obvious all the elements of claims 12-14, 18-24, 26, and 28 as explained in the rejection of the claims that is set forth in this Office action.
In response to the applicant’s argument that Zhong teaches a two step reaction and that neither Zhang or Zhong teaches the process described in the pending claims (p. 5), the rejection of the claims that is set forth in this Office is not based on Zhang or Zhong individually teaching the process of the pending claims and is not based on either of them individually teaching the claimed one step reaction. The rejection of claim 12 is based on Zhang rendering it obvious that the process comprises adding a first compound comprising one or more of a primary amine group and a secondary amine group, a second compound comprising an ether group and one or more of a primary amine group and a secondary amine group, a cardanol, and a formaldehyde to a reaction vessel, reacting the cardanol with the first compound comprising one or more of a primary amine group and a secondary amine group and the second compound comprising an ether group and one or more of a primary amine group and a secondary amine group in the presence of the formaldehyde as claimed. The rejection of claim 12 is also based on the combination of Zhang in view of Zhong rendering it obvious that the process further comprises adding an acid catalyst to the reaction vessel, and the reacting in the presence of a formaldehyde is further in the presence of the catalyst as claimed. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to carry out Zhang’s reacting CNSL, paraformaldehyde, and polyamines in the presence of Zhong’s acid catalyst in Zhang’s round flask. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for catalyzing Zhang’s reacting CNSL, paraformaldehyde, and polyamines in Zhang’s round flask because Zhong teaches acid catalyst that is used [0009] in a preparation method of phenolic amine type Mannich base occlusive agents comprising [0008] adding an alcohol-water solvent, formalin solution, and alkylamine, along with a few drops of the acid catalyst to a reaction vessel 1, adding phenol to a reaction vessel 2 and dissolving it in an alcohol-water solvent, adding the solution from reaction vessel 1 to reaction vessel 2, reacting, and obtaining phenol-aldehyde-amine type Mannich base compound [0009], wherein the phenol can be phenol or o-cresol [0017], wherein the alkylamine is dimethylamine, diethylamine, or diethanolamine [0018], which is substantially similar to Zhang’s reacting CNSL, paraformaldehyde, and polyamines because Zhang teaches preparing a phenalkamine compound by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082] in a round flask [0081, 0083], wherein the CNSL mainly comprises cardanol and cardol [0019], that the polyamine for preparing the phenalkamine compound can be aliphatic, cycloaliphatic, aromatic, polycyclic, polyamide, polyamidoamine, or mixtures thereof [0020], that examples of suitable aliphatic polyamines include diethylenetriamine (DETA) [0020], that examples of suitable polyoxyalkylene polyamines include JEFFAMINETM D-230 and JEFFAMINE D-400 polyoxypropylenediamines [0020], and that in some embodiments, the polyamines used are DETA, polyoxyproylenediamine, polyoxyethylenediamine, or mixtures thereof [0020]. One cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. The combination of Zhang in view of Zhong renders obvious claims 12-14, 18-24, and 28 as explained in the rejection of the claims that is set forth in this Office action. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).
In response to the applicant’s argument that Zheng does not cure the deficiencies of Zhang and Liu with regard to claim 12 (p. 5), Zhang in view of Liu does not have deficiencies with regard to claim 12 as explained above in the Office’s response to the applicant’s arguments against Zhang in view of Liu.
In response to the applicant’s argument that Zheng does not cure the deficiencies of Zhang and Zhong with regard to claim 12 (p. 5), Zhang in view of Zhong does not have deficiencies with regard to claim 12 as explained above in the Office’s response to the applicant’s arguments against Zhang in view of Zhong.
In response to the applicant’s argument that although the wording of claim 29 varies slightly from claim 12, the concept of a single step reaction is the same (p. 5), the rejection of claim 29 is not based on Zhang, Liu, or Zheng individually teaching the claimed single step reaction. The rejection of claim 29 is based on Zhang rendering it obvious that the process comprises in the presence of formaldehyde, reacting a cardanol with triethylenetetramine and a polyetheramine as claimed. The rejection of claim 29 is based on the combination of Zhang in view of Liu rendering it obvious that the process comprises further in the presence of oxalic acid, reacting the cardanol as claimed. The rejection of claim 29 is based on the combination of Zhang in view of Zheng rendering it obvious that the process comprises further reacting a bisphenol with the triethylenetetramine and the polyetheramine as claimed. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to carry out Zhang’s reacting in the presence of Liu’s acidic catalyst that is oxalic acid. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for catalyzing Zhang’s reacting CNSL, formaldehyde, and polyamines because Liu teaches an acidic catalyst [0021] that is oxalic acid [0026] and that is used [0021] in a method for preparing a Mannich base curing agent comprising [0020] mixing tung oil and phenol and subjecting to Friedel-Crafts substitution reaction under the catalysis of the acid catalyst [0021], adding amines to the reaction system of the previous step to carry out a salt formation reaction, then adding aldehydes to the reaction system to carry out a Mannich reaction [0022], heating the product to complete the polycondensation reaction [0023], heating the crude curing agent obtained in the previous step, and distilling it under normal and reduced pressure to remove low-boiling substances and moisture from the reaction system [0024], wherein the phenols are phenol, o-cresol, mixed cresol, nonylphenol, p-tert-butylphenol, resorcinol, and bisphenol A [0013], wherein the aldehydes are optionally formaldehyde [0014], wherein the amines are one or more of ethylenediamine, hexamethylenediamine, diethylenetriamine, triethylenetetramine, polyethylene polyamine, m-phenylenediamine, m-phenylenediamine, isophorone diamine, and dimethylamine [0015], which is substantially similar to Zhang’s reacting CNSL, paraformaldehyde, and polyamines because Zhang teaches preparing a phenalkamine compound by reacting CNSL, paraformaldehyde [0080, 0082], and polyoxypropylenediamine [0080] or diethylenetriamine [0082], that the CNSL mainly comprises cardanol and cardol [0019], that formaldehyde is optionally used instead of the paraformaldehyde [0020], that formaldehyde is optionally used instead of the paraformaldehyde [0020], that the polyamine for preparing the phenalkamine compound can be aliphatic, cycloaliphatic, aromatic, polycyclic, polyamide, polyamidoamine, or mixtures thereof [0020], that examples of suitable aliphatic polyamines include diethylenetriamine (DETA) and triethylenetetramine (TETA) [0020], and that examples of suitable polyoxyalkylene polyamines include JEFFAMINETM D-230 and JEFFAMINE D-400 polyoxypropylenediamines [0020]. One cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).
In response to the applicant’s argument that claims 29-31 are patentable for the same reasons as presented above with regard to claim 12 (p. 5), Zhang in view of Liu and Zheng renders obvious claims 29-31 as explained in the rejection of the claims that is set forth in this Office action.
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.
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/DAVID T KARST/Primary Examiner, Art Unit 1767
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