DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claim Objections
Claim 28 is objected to because of the following informalities: Claim 28 depends from claim 23, however claim 23 has been cancelled. It appears that instead claim 28 should depend from claim 27, as this is the first recitation of “a first functional group” and “a second functional group”. Appropriate correction is required.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim(s) 25, 29-31, 34, 51, 55 and 56 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Deorkar et al (US PGPub 2008/0203029), as cited on the IDS.
Regarding Claim 25, Deorkar et al teaches a method for modifying a support material for use as a stationary phase in an analytical or preparative separation process (such as a chromatographic process) (see [0019]), comprising the steps:
a) providing a support material (referred to as polymeric chromatographic media, i.e. polymeric resin) (see [0020]-[0025]),
b) coating the support material with an oligoamine or polyamine (to form PEI) (see [0019], [0034] and [0063]),
c) reacting the support material with a compound comprising - a first functional group reactive with amines and/or hydroxy groups, preferably an epoxy group, and an ion-exchange group, preferably a quaternary organo-element of main group V, preferably a quaternary ammonium group (see examples 1, 25, 29 and 30), wherein step b) and c) are performed in sequence (see [0031] and [0034]).
Regarding Claim 29, Deorkar et al teaches that the oligoamine or polyamine in step b) is selected from the group consisting of polyallylamine, linear or branched polyethyleneimine (PEI), poly(2-methylaziridine) (specifically PEI) (See [0019] and [0025]).
Regarding Claim 30, Deorkar et al teaches that the compound used in step c) is of Formula I X-R
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R2 (I) with R being a linear or branched alkyl or ether group; with each of R1, R2 or R3 being selected independently from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloaklyl or five- or six- membered heterocycle formed between R1 and R2 or R2 and R3 or R1 and R3 and with X being the functional group reactive with amines and/or hydroxyl groups (see [0032] and Examples 25, 29 and 30).
Regarding Claim 31, Deorkar et al teaches that the compound is of formula I and R is selected from the linear or branched alkyl or ether group consisting of -(CH2)n- or -(CH2)n-O-(CH2)n- with n being selected from 1, 2, 3, 4, 5, 6, 7, 8, 9,10; and wherein R1, R2 and R3 each or independently being - an alkyl group selected from the group consisting of -CH3 and -(CH2)n-CH3, with n being selected from 1, 2, 3, 4, 5, 6, 7,8,9, 10; or - an alkyl alcohol group selected from the group of linear or branched alkyl alcohols, preferably selected from the group consisting of -(CH2)n-OH, with n = being selected from 1, 2,3,4,5,6,7,8, 9, 10 (see [0032] and Examples 25, 29 and 30).
Regarding Claim 34, Deorkar et al teaches that the compound used in step c) is a (Halogenoalkyl)trialkylammonium halogenide selected from the group consisting of:(3-Chloro-2-hydroxypropyl)trimethylammonium chloride, (2-Chloroethyl)trimethylammonium chloride, (2-Bromoethyl)trimethylammonium bromide, (3-Bromopropyl)trimethylammonium bromide, (5-Bromopentyl)trimethylammonium bromide (specifically, 3-chloro-2-hydroxypropyl)trimethylammonium chloride) (see [0025]).
Regarding Claim 51, Deorkar et al teaches a support material (referred to as chromatographic media) for use as a stationary phase (chromatographic column) in an analytical or preparative separation process obtainable by a method according to claim 25 (see [0025] and [0032]-[0033]).
Regarding Claim 55, Deorkar et al teaches a chromatography column filled with a support material according to claim 51 (see [0081], and examples 25,29 and 30).
Regarding Claim 56, Deorkar et al teaches a method of chromatographic separation of analytes, wherein a solution containing the analytes is contacted with polymer support material according to claim 51 (see [0033], [0081], and examples 25,29 and 30).
Claim(s) 25-31, 33-36, 46 and 51-56 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Wu et al (US 6780327), as cited on the IDS.
Regarding Claim 25, Wu et al teaches a method for modifying a support material for use as a stationary phase in an analytical or preparative separation process (see col. 8, lines 54-60; col. 4, lines 22-24) comprising the steps:
a) providing a support material (see col. 3, line 34, 46-47; col. 4, lines 19-20);
b) coating the support material with polyamine (see col. 3, line 49-50; col. 4, lines 20-21 );
c) reacting the polyamine with a compound comprising a first functional group reactive with amines and/or hydroxy groups such as an epoxy group (see col. 5, lines 18-24, col. 3, line 52; and col. 4, line 26-27;) , and a quaternary ammonium ion-exchange group (see col. 5, lines 23-24), wherein the polyamine is reacted with said compound before being coated on the support material, such that steps b) and c) are performed in sequence or simultaneously (see Col. 3, line – Col. 5, line 50).
Furthermore, Wu et al teaches that the modified polymeric support material can be used as a stationary phase in an analytical or preparative separation process (see col. 12, line 42; col. 3, line 33).
Regarding Claim 26, Wu et al teaches that step c) is followed by a crosslinking step, treating the reaction product resulting from step c) with one or more polyfunctional compounds (such as epoxies) (see Col. 8, lines 33-41 and Examples 5-10).
Regarding Claims 27-28, Wu et al teaches that the one or more polyfunctional compound in step d) has - at least a first functional group reactive with amines and/or hydroxy groups, and at least a second functional group reactive with amines and/or hydroxy groups and more specifically that the first functional group is an epoxy group and wherein the second functional group is an epoxy group (see Col. 5, lines 18-24 and examples 5-10).
Regarding Claim 29, Wu et al teaches that the oligoamine or polyamine in step b) is selected from the group consisting of polyallylamine, linear or branched polyethyleneimine (PEI), poly(2-methylaziridine) (specifically, PEI) (see Col. 5, lines 18-24 and Col. 6, lines 32-49).
Regarding Claim 30, Wu et al teaches that the compound used in step c) is of Formula I X-R
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R2 (I) with R being a linear or branched alkyl or ether group; with each of R1, R2 or R3 being selected independently from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloaklyl or five- or six- membered heterocycle formed between R1 and R2 or R2 and R3 or R1 and R3 and with X being the functional group reactive with amines and/or hydroxyl groups (see Col. 5, lines 18-24).
Regarding Claim 31, Wu et al teaches that the compound is of formula I and R is selected from the linear or branched alkyl or ether group consisting of -(CH2)n- or -(CH2)n-O-(CH2)n- with n being selected from 1, 2, 3, 4, 5, 6, 7, 8, 9,10; and wherein R1, R2 and R3 each or independently being - an alkyl group selected from the group consisting of -CH3 and -(CH2)n-CH3, with n being selected from 1, 2, 3, 4, 5, 6, 7,8,9, 10; or - an alkyl alcohol group selected from the group of linear or branched alkyl alcohols, preferably selected from the group consisting of -(CH2)n-OH, with n = being selected from 1, 2,3,4,5,6,7,8, 9, 10 (see Col. 5, lines 18-24).
Regarding Claim 33, Wu et al teaches that the compound used in step c) is of Formula (I), selected from the group consisting of glycidyltrimethylammonium chloride; glycidylmethyldethanolammonium chloride; and glycidyltriethylammonium chloride (see Col. 18, lines 37-47).
Regarding Claim 34, Wu et al teaches that the compound used in step c) is a (Halogenoalkyl) trialkylammonium halogenide selected from the group consisting of: (3-Chloro-2-hydroxypropyl) trimethylammonium chloride, (2-Chloroethyl) trimethylammonium chloride, (2-Bromoethyl) trimethylammonium bromide, (3-Bromopropyl) trimethylammonium bromide, (5-Bromopentyl) trimethylammonium bromide (see Col. 18, lines 37-47).
Regarding Claims 35-36, Wu et al teaches that polyfunctional compound(s) used in step d) is/are selected from -epoxides; halogenalkanes; or aldehydes, wherein
the epoxides are selected from 1,4-butanedioldiglycidyl ether, trimethylolpropane triglycidyl ether, poly(ethylene glycol) diglycidyl ether, resorcinol diglycidyl ether, glycerol diglycidyl ether, glycidol; and wherein the halogenalkanes are select-ed from epichlorohydrin, epibromohydrin, 1,1'-Oxybis[2-(2-chloroethoxy)ethane]; and 1,2-Bis(2-chloroethoxy)ethane, bis(2-chloroethyl) ether, 1-Chloro-3- iodopropane, 1,4-dibromobutane, 1,3-dibromopropane; and wherein the aldehyde is glutaraldehyde (see Col. 8, lines 33-41; Col. 17, lines 17 and 63 and Col. 18, lines 24-25).
Regarding Claim 46, Wu et al teaches that the support material provided in step a) is selected from the group consisting of hydrocarbon-based compounds; PVA; sugar-based compounds; inorganic compounds (such as polyaromatics, polysulfones, polyamides, polyimides, polyolefins, polystyrenes, polycarbonates, cellulosic polymers such as cellulose acetates and cellulose nitrates, fluoropolymers, and PEEK. Aromatic polysulfones are preferred. Examples of aromatic polysulfones include polyethersulfone, bisphenol A polysulfone, and polyphenylsulfone.) (see Col. 8, lines 52-63).
Regarding Claim 51, Wu et al teaches a support material (referred to as a positively charged microporous membrane comprising a hydrophilic porous substrate) for use as a stationary phase in an analytical or preparative separation process obtainable by a method according to claim 25 (see Col. 4, lines 17-31).
Regarding Claim 52, Wu et al teaches that the support material provided in step a) is microporous or mesoporous (see Col. 4, line 18 and Col. 9, line 42).
Regarding Claims 53-54, Wu et al teaches that thesupport material according to claim 51, is stable in a pH range from 0 to 14 such that the retention time of sulfate in a column packed thereof after one-time rinsing with 1 M NaOH solution and/or one-time rinsing with 1M HNO3 solution does not differ by more than 8% from the retention time of sulfate before such rinsing (see Col. 11, line 64 – Col. 12, line 38).
Regarding Claim 55, Wu et al teaches a chromatography column filled with a support material according to claim 51 (see Col. 13, lines 35-47).
Regarding Claim 56, Wu et al teaches a method of chromatographic separation of analytes, wherein a solution containing the analytes is contacted with polymer support material according to claim 51 (see Col. 12, lines 39 – 64).
Claim Rejections - 35 USC § 103
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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
Claim(s) 26-28, 35 and 46 are rejected under 35 U.S.C. 103 as being unpatentable over Deorkar et al as applied to claims 25 and 26 above, and further in view of Marcus et al (US PGPub 2016/0266134).
Regarding Claims 26-28, Deorkar et al does not disclose that step c) is followed by a crosslinking step, treating the reaction product resulting from step c) with one or more polyfunctional compounds and that the one or more polyfunctional compound in step d) has at least a first functional group reactive with amines and/or hydroxy groups, and at least a second functional group reactive with amines and/or hydroxy groups and more specifically that the first functional group is an epoxy group and wherein the second functional group is an epoxy group.
However, in the analogous art of crosslinked polymer stationary phase for chromatography, Marcus et al teaches a surface of a support phase can be modified to include a crosslinked polymer network as stationary phase to perform separation of one or more species from a liquid in highly efficient separations based on chemical interactions, i.e., chromatography (see abstract). Furthermore, Marcus et al teaches that the polymer can be crosslinked by use of any suitable crosslinking agent that can crosslink the polymer without destroying the desired interactivity capability of the polymer with the analyte of interest. The crosslinking agent can include a polyfunctional compound that can react with functionality of the polymer to form crosslinks within and among the polymer chains on the surface of the support phase. In general, the crosslinking agent can be a non-polymeric compound, i.e., a molecular compound that includes two or more reactively functional terminal moieties linked by a bond or a non-polymeric (non-repeating) linking component. By way of example, the crosslinking agent can include but is not limited to di-epoxides, poly-functional epoxides, diisocyanates, polyisocyanates, polyhydric alcohols, water-soluble carbodiimides, diamines, diaminoalkanes, polyfunctional carboxylic acids, diacid halides, polyglycidyl ethers, such as ethylene glycol diglycidyl ether, 1,4-butane diglycidyl ether, and polyethylene glycol dicglycidyl ether; acrylamides; compounds containing one or more hydrolyzable groups, such as alkoxy groups (e.g., methoxy, ethoxy and propoxy); alkoxyalkoxy groups (e.g., methoxyethoxy, ethoxyethoxy and methoxypropoxy); acyloxy groups (e.g., acetoxy and octanoyloxy); ketoxime groups (e.g., dimethylketoxime, methylketoxime and methylethylketoxime); alkenyloxy groups (e.g., vinyloxy, isopropenyloxy, and 1-ethyl-2-methylvinyloxy); amino groups (e.g., dimethylamino, diethylamino and butylamino); aminoxy groups (e.g., dimethylaminoxy and diethylaminoxy); and amide groups (e.g., N-methylacetamide and N-ethylacetamide) (see [0065]). Furthermore, Marcus et al teaches that the BUDGE crosslinking creates a more dense PEI architecture, which also contains some of the hydrophilic character of the epoxide linkers (see [0126]). Accordingly, it would have been obvious to one of ordinary skill in the art to modify the method of Deorkar et al by treating the reaction product of step c) with a crosslinked epoxide (which is reactive with amines and/or hydroxy of the reaction product) for the benefit of creating a more dense PEI architecture, while imparting some hydrophilic characteristics to the reaction product.
Regarding Claim 35, Deorkar et al does not teach that the polyfunctional compound(s) used in step d) is/are selected from - epoxides; - halogenalkanes; - aldehydes.
However, in the analogous art of crosslinked polymer stationary phase for chromatography, Marcus et al teaches BUDGE crosslinking, which creates a more dense PEI architecture, which also contains some of the hydrophilic character of the epoxide linkers (see [0126]). In addition, Marcus et al teaches that teaches a surface of a support phase can be modified to include a crosslinked polymer network as stationary phase to perform separation of one or more species from a liquid in highly efficient separations based on chemical interactions, i.e., chromatography (see abstract). Furthermore, Marcus et al teaches that the polymer can be crosslinked by use of any suitable crosslinking agent that can crosslink the polymer without destroying the desired interactivity capability of the polymer with the analyte of interest with a polyfunctional group (such as an epoxide)(see abstract and [0065]). Accordingly, it would have been obvious to one of ordinary skill in the art to modify the method of Deorkar et al by treating the reaction product of step c) with a crosslinked epoxide (which is reactive with amines and/or hydroxy of the reaction product) for the benefit of creating a more dense PEI architecture, while imparting some hydrophilic characteristics to the reaction product.
Regarding Claim 46, Deorkar et al does not teach the support material provided in step a) is selected from the group consisting of hydrocarbon-based compounds; PVA; sugar-based compounds; inorganic compounds.
However, in the analogous art of crosslinked polymer stationary phase for chromatography, Marcus et al teaches that the surface modifications can be carried out in addition to the inclusion of the crosslinked polymer as stationary phase on the support phase. For example, in one embodiment, a predetermined chemical reactivity can be obtained by modifying at least portions of the surfaces of a polymeric support phase to a predetermined level of hydrophobicity. Thus, active sites on the fiber surfaces can be functionalized to gain more or less hydrophobic character. A predetermined chemical reactivity also can be obtained by modifying at least portions of the surface of the support phase to a predetermined ionic character. For example, the surfaces of fibers 20 formed from polyvinyl alcohol (PVA) might be protonated in situ by an acidic mobile. Such additional modification can be carried out in the same surface location of the support phase as at the crosslinked polymer or in a different area, as desired (see [0079]). Accordingly, it would have been obvious to one of ordinary skill in the art to utilize PVA to form the support with a predetermined ionic character.
Claim 33 is rejected under 35 U.S.C. 103 as being unpatentable over Deorkar et al as applied to claim 30 above, and further in view of Komiya et al (WO 2006/13233).
Regarding Claim 33, Deorkar et al does not teach that the compound used in step c) is of Formula (I), selected from the group consisting of glycidyltrimethylammonium chloride; glycidylmethyldiethanolammonium chloride; and glycidyltriethylammonium chloride.
However, in the analogous art of packing materials used in liquid chromatography, Komiya et al teaches that when the base point of the reaction is an alcoholic OH group, a cation exchange resin can be obtained by reacting with bromoethyl sulfonic acid, monochloroacetic acid, 1,3-propane sultone, or the like. Further, if it is reacted with 2-chloroethyldetylamamine hydrochloride, glycidyltrimethylammonium chloride, etc., it is possible to obtain a cation-exchanged resin. Furthermore, an epoxy group can also be introduced by reacting with epino or rhohydrin (see [0065]). Accordingly, it would have been obvious to one of ordinary skill in the art to react the support with glycidyltrimethylammonium chloride (as taught by Komiya et al) for the benefit of forming a cation-exchanged resin and providing hydrophilicity.
Claim 36-39 and 41-45 is rejected under 35 U.S.C. 103 as being unpatentable over Deorkar et al et al as applied to claims 25 and 26 above, and further in view of Demmer et al (US PGPub 2011/0147292).
Regarding Claims 36, Deorkar et al does not teach that the epoxides are selected from 1,4-butanedioldiglycidyl ether, trimethylolpropane triglycidyl ether, poly(ethylene glycol) diglycidyl ether, resorcinol diglycidyl ether, glycerol diglycidyl ether, glycidol; and wherein the halogenalkanes are select-ed from epichlorohydrin, epibromohydrin, 1,1'-Oxybis[2-(2-chloroethoxy)ethane]; and 1,2-Bis(2-chloroethoxy)ethane, bis(2-chloroethyl) ether, 1-Chloro-3- iodopropane, 1,4-dibromobutane, 1,3-dibromopropane; and wherein the aldehyde is glutaraldehyde.
However, in the analogous art of membrane chromatography, Demmer et al teaches a cellulose hydrate membrane for membrane chromatography, wherein the membrane is constructed of the cellulose hydrate membrane obtained following any pretreatment carried out and following the hydrolysis with swelling is crosslinked with a crosslinking agent to increase the chemical resistance of the membrane and/or to introduce functional groups. The crosslinking agent has at least two functional groups in the molecule which are reactive with the hydroxyl groups of cellulose and thus make crosslinking of cellulose possible. The usable crosslinking agents are, in principle, not subject to any particular restrictions and a person skilled in the art is capable of selecting them from a series of crosslinking agents usable for the crosslinking of cellulose. However, it is preferred to use, in the crosslinking step, a diepoxide compound or else other compounds which are reactive with hydroxyl groups of cellulose and have at least two reactive functional groups, such as diisocyanate, epichlorohydrin, epibromohydrin, dimethylurea, dimethylethyleneurea, dimethylchloro-silane, bis(2-hydroxyethyl) sulfone, divinyl sulfone, alkylene dihalogen, hydroxyalkylene dihalogen, and glycidyl ethers. From the group of the glycidyl ethers, preference is given to 1,4-butanediol diglycidyl ether, ethylene glycol diglycidyl ether, glycerol diglycidyl ether, and polyethylene glycol diglycidyl ether (see [0048]-[0050]). Accordingly, it would have been obvious to cross link the reaction product of step c) with 1,4-butanediol diglycidyl ether, ethylene glycol diglycidyl ether, glycerol diglycidyl ether, and polyethylene glycol diglycidyl ether (as taught by Demmer et al) for the benefit of enabling effective crosslinking with a cellulose hydrate and thus increase the chemical resistance of the membrane.
Regarding Claims 37-39, Deorkar et al does not teach that the reaction product resulting from step c) is treated with one or more monofunctional compounds, wherein the monofunctional compound is a compound having a functional group reactive with amines and/or hydroxy groups and wherein the monofunctional compound is selected from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloaklyl.
However, in the analogous art of membrane chromatography, Demmer et al teaches a cellulose hydrate membrane for membrane chromatography and introducing functional groups during the crosslinking, e.g., by adding an amine and/or a monofunctional epoxide compound, such as phenyl glycidyl ether or butyl glycidyl ether, to a diepoxide compound (see abstract and [0060]). Accordingly it would have been obvious to one of ordinary skill in the art to cross link the reaction product of step c) with a monofunctional epoxide compound, such as phenyl glycidyl ether or butyl glycidyl ether, to a diepoxide compound (as taught by Demmer al) for the benefit of enabling effective crosslinking with a cellulose hydrate and thus increasing the chemical resistance of the membrane.
Regarding Claim 41, Deorkar et al does not teach that the PEI is covalently attached to the support material.
However, in the analogous art of membrane chromatography, Demmer et al teaches a cellulose hydrate membrane for membrane chromatography (see abstract) and teaches polymers which have a linear, branched, or cyclic structure and which contain primary, secondary, and/or tertiary amine groups are highly suitable for covalent immobilization on activated surfaces. Such polymers offer a sufficient number of cationic groups which are capable of adsorbing negatively charged substances. The direct covalent attachment of polymeric amines to porous supports leads to stable positively charged surfaces (see [0064]). It would have been obvious to one of ordinary skill in the art to covalently attach the PEI (i.e. the coating) to the support for the benefit of providing a stable positively charged surface.
Regarding Claims 42-45, Deorkar et al does not teach that the PEI is attached to the support material by means of a spacer molecule, and wherein the spacer is a polyfunctional molecule with a group reactive with alcohols/amines and the other group reactive with polyamine and wherein the support material provided in step a) comprises groups that are reactive with the spacer molecule (containing epoxides) on the substrate end.
However, in the analogous art of membrane chromatography, Demmer et al teaches a cellulose hydrate membrane for membrane chromatography (see abstract) and that functional groups are bonded to the cellulose membrane via epoxide groups or aldehyde groups. Furthermore, it is also possible to introduce functional groups during the crosslinking, e.g., by adding an amine and/or a monofunctional epoxide compound, such as phenyl glycidyl ether or butyl glycidyl ether, to a diepoxide compound and the functional groups can be a constituent of an oligomeric or polymeric spacer which links the functional groups to the cellulose membrane. In addition, particularly preferably, the functional groups are ligands which preferably comprise anionic or cationic groups. The anionic groups can, for example, be sulfonic acid, phosphoric acid, or carboxylic acids, and the cationic groups can be primary, secondary, tertiary, and/or quaternary amines (see [0059]-[0062]).It would have been obvious to one of ordinary skill in the art to crosslink the support with a spacer reactive with an alcohol/amine and also reactive with polyamine for the benefit of enabling effective crosslinking with a cellulose hydrate (the support) and thus increasing the chemical resistance of the membrane.
Claim 37-39 and 41-45 is rejected under 35 U.S.C. 103 as being unpatentable over Wu et al et al as applied to claims 25 and 26 above, and further in view of Demmer et al (US PGPub 2011/0147292).
Regarding Claims 37-39, Wu et al does not teach that the reaction product resulting from step c) is treated with one or more monofunctional compounds, wherein the monofunctional compound is a compound having a functional group reactive with amines and/or hydroxy groups and wherein the monofunctional compound is selected from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloaklyl.
However, in the analogous art of membrane chromatography, Demmer et al teaches a cellulose hydrate membrane for membrane chromatography and introducing functional groups during the crosslinking, e.g., by adding an amine and/or a monofunctional epoxide compound, such as phenyl glycidyl ether or butyl glycidyl ether, to a diepoxide compound (see abstract and [0060]). Accordingly it would have been obvious to one of ordinary skill in the art to cross link the reaction product of step c) with a monofunctional epoxide compound, such as phenyl glycidyl ether or butyl glycidyl ether, to a diepoxide compound (as taught by Demmer al) for the benefit of enabling effective crosslinking with a cellulose hydrate and thus increasing the chemical resistance of the membrane.
Regarding Claim 41, Wu et al does not teach that the PEI is covalently attached to the support material.
However, in the analogous art of membrane chromatography, Demmer et al teaches a cellulose hydrate membrane for membrane chromatography (see abstract) and teaches polymers which have a linear, branched, or cyclic structure and which contain primary, secondary, and/or tertiary amine groups are highly suitable for covalent immobilization on activated surfaces. Such polymers offer a sufficient number of cationic groups which are capable of adsorbing negatively charged substances. The direct covalent attachment of polymeric amines to porous supports leads to stable positively charged surfaces (see [0064]). It would have been obvious to one of ordinary skill in the art to covalently attach the PEI (i.e. the coating) to the support for the benefit of providing a stable positively charged surface.
Regarding Claims 42-45,Wu et al does not teach that the PEI is attached to the support material by means of a spacer molecule, and wherein the spacer is a polyfunctional molecule with a group reactive with alcohols/amines and the other group reactive with polyamine and wherein the support material provided in step a) comprises groups that are reactive with the spacer molecule (containing epoxides) on the substrate end.
However, in the analogous art of membrane chromatography, Demmer et al teaches a cellulose hydrate membrane for membrane chromatography (see abstract) and that functional groups are bonded to the cellulose membrane via epoxide groups or aldehyde groups. Furthermore, it is also possible to introduce functional groups during the crosslinking, e.g., by adding an amine and/or a monofunctional epoxide compound, such as phenyl glycidyl ether or butyl glycidyl ether, to a diepoxide compound and the functional groups can be a constituent of an oligomeric or polymeric spacer which links the functional groups to the cellulose membrane. In addition, particularly preferably, the functional groups are ligands which preferably comprise anionic or cationic groups. The anionic groups can, for example, be sulfonic acid, phosphoric acid, or carboxylic acids, and the cationic groups can be primary, secondary, tertiary, and/or quaternary amines (see [0059]-[0062]).It would have been obvious to one of ordinary skill in the art to crosslink the support with a spacer reactive with an alcohol/amine and also reactive with polyamine for the benefit of enabling effective crosslinking with a cellulose hydrate (the support) and thus increasing the chemical resistance of the membrane.
Claims 47-50, 53 and 54 are rejected under 35 U.S.C. 103 as being unpatentable over Deorkar et al (or Wu et al) as applied to claims 30 and 51 above, and further in view of Seubert et al (US PGPub 2022/0204712).
Regarding Claim 47, neither Deorkar et al (nor Wu et al) teaches generating hydroxy groups on/in the support material, previous to step b), by a process comprising the steps of - oxidative treatment of the polymer support substrate; and subsequent - reductive or hydrolytic treatment.
However, in the analogous art of modifying polymer carrier materials, Seubert et al teaches a method for modifying a polymer carrier material for use as a stationary phase in an analytical or preparative separating method, the method comprising the steps of: providing a polymer carrier material, which is at least partly formed of aromatic hydrocarbon compounds comprising at least two vinyl or allyl substituents; producing hydroxy groups on/in the polymer carrier material by a method comprising an oxidative treatment of the polymer carrier material and a subsequent reductive or hydrolytic treatment of the reaction product; reacting the product from the previous step with a polyfunctional compound (see abstract). It would have been obvious to one of ordinary skill in the art to generate hydroxy groups on/in the support material, previous to step b), by a process comprising the steps of oxidative treatment of the polymer support substrate; and subsequent reductive or hydrolytic treatment for the benefit of effectively rendering the support accessible to subsequent reduction or hydrolysis.
Regarding Claims 48-49, neither Deorkar et al (nor Wu et al) teaches that the support material is - partially derived from aromatic hydrocarbon compounds having at least two vinyl or allyl substituents; and- partially derived from monomers selected from the group of ethylvinylbenzene, vinyl acetate, styrene and any combination thereof.
However, in the analogous art of modifying polymer carrier materials, Seubert et al teaches that the polymeric carrier material in step a, which is at least partially formed from aromatic hydrocarbon compounds having at least two vinyl or allyl substituents, is additionally partially formed from monomers selected from the group consisting of ethylvinylbenzene, vinyl acetate, styrene, and a combination thereof. In this regard, the proportion of aromatic hydrocarbon compounds having at least two vinyl or allyl substituents is preferably at least 50% by weight (see [0031]). It would have been obvious to one of ordinary skill in the art that the support material is at least partially derived from aromatic hydrocarbon compounds, such as ethylvinylbenzene, vinyl acetate, styrene, or a combination thereof, for the benefit of ensuring the support has the desired hydrophilicity.
Regarding Claim 50, neither Deorkar et al (nor Wu et al) teaches that step c) or d) is followed by a step e) heating the functionalized and crosslinked material in alkaline solution.
However, in the analogous art of modifying polymer carrier materials, Seubert et al teaches heating the polymer support material provided with ion exchange groups in alkaline solution. This allows the selectivity and capacity of the ion exchange material from the previous step to be adjusted. The treatment is hereinafter referred to as elimination and consists in particular in heating the particles provided with exchange groups in aqueous alkaline solution, particularly preferably in heating in an aqueous solution of alkali metal or alkaline earth metal hydroxide or carbonate, for example in sodium hydroxide solution (see [0049]). It would have been obvious to one of ordinary skill in the art to modify the method of either Deorkar et al (or Wu et al) by heating the polymer support material provided with ion exchange groups in alkaline solution for the benefit of allowing for the selectivity and capacity of the ion exchange material from the previous step to be adjusted.
Regarding Claims 53-54, neither Deorkar et al (nor Wu et al) teaches that the material is stable in a pH range from 0 to 14 such that the retention time of sulfate in a column packed thereof after one-time rinsing with 1 M NaOH solution and/or one-time rinsing with 1M HNO3 solution does not differ by more than 8% from the retention time of sulfate before such rinsing.
However, in the analogous art of modifying polymer carrier materials, Seubert et al teaches the that modified polymer support material is stable in the pH range of 0 to 14. By pH stable it is understood here that the retention time of sulfate in a column packed with modified polymer support material after rinsing with 1M NaOH solution and/or rinsing with 1M HCl solution does not deviate more than 8%, preferably not more than 5%, more preferably not more than 3% from the retention time of sulfate in a column packed with modified polymer support material not previously exposed to pH values of 0 and/or 14 (see [0083]). It would have been obvious to modify the method of either Deorkar et al or Wu et al by rinsing the support with 1M NaOH solution and/or rinsing with 1M HCl solution does not deviate more than 8%, preferably not more than 5%, more preferably not more than 3% from the retention time of sulfate in a column packed with modified polymer support material not previously exposed to pH values of 0 and/or 14) in order to produce a pH and mechanically stable support.
Claim 50 is rejected under 35 U.S.C. 103 as being unpatentable over Deorkar et al et al (or Wu et al) as applied to claim 25 above, and further in view of Iemura et al (US PGPub 2021/0237034), cited on the IDS.
Regarding Claim 50, neither Deorkar et al (nor Wu et al) teaches that step c) or d) is followed by a step e) heating the functionalized and crosslinked material in alkaline solution.
However, in the analogous art of packing material for ion chromatography, Iemura et al teaches that alkaline treatment may be carried out on packing material obtained by reaction in order to enhance the stability with respect to the alkaline eluent. The alkaline treatment takes place by stirring under heating in an alkaline aqueous solution. This alkaline treatment is implemented in order to make fine adjustments to the retention time of the column obtainable from the packing material, or in order for a column to indicate a stabilized baseline (see [0054]). It would have been obvious to one of ordinary skill in the art to modify the method of Wu et al or Deorkar et al by heating the crosslinked material in alkaline solution (as claimed by Iemura et al) for the benefit of enhancing the stability of the support.
Allowable Subject Matter
Claims 32 and 40 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Regarding Claim 32, the prior art neither teaches nor fairly suggests that he compound is of formula II,III or IV
PNG
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155
332
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(II) (III) (IV) with R being selected from the linear or branched alkyl or ether group consisting of -(CH2)n- or -(CH2)n-O-(CH2)n- with n being selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10.
Regarding Claim 40, the prior art neither teaches nor fairly suggests that the monofunctional compound is selected from halogene alkanes or epoxy alkanes.
Conclusion
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/JENNIFER WECKER/ Primary Examiner, Art Unit 1797