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Patent US20060180549 - Organosilanes and substrates covalently bonded with same and methods for ... - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inAdvanced Patent SearchPatentsThe present invention provides novel silicon compounds, methods for making these novel silicon compounds, compositions comprising these novel silicon compounds attached to substrates, methods for attaching the novel silicon compounds to substrates and methods for using the compositions in a variety of...http://www.google.com/patents/US20060180549?utm_source=gb-gplus-sharePatent US20060180549 - Organosilanes and substrates covalently bonded with same and methods for synthesis and use sameAdvanced Patent SearchPublication numberUS20060180549 A1Publication typeApplicationApplication numberUS 11/059,179Publication dateAug 17, 2006Filing dateFeb 15, 2005Priority dateFeb 15, 2005Also published asCA2597899A1, CN101120007A, EP1848726A1, EP1848726B1, US7468130, US20090130767, WO2006088760A1Publication number059179, 11059179, US 2006/0180549 A1, US 2006/180549 A1, US 20060180549 A1, US 20060180549A1, US 2006180549 A1, US 2006180549A1, US-A1-20060180549, US-A1-2006180549, US2006/0180549A1, US2006/180549A1, US20060180549 A1, US20060180549A1, US2006180549 A1, US2006180549A1InventorsXiaodong Liu, Christopher PohlOriginal AssigneeDionex CorporationExport CitationBiBTeX, EndNote, RefManReferenced by (8), Classifications (13), Legal Events (3) External Links: USPTO, USPTO Assignment, EspacenetOrganosilanes and substrates covalently bonded with same and methods for synthesis and use same
US 20060180549 A1Abstract
The present invention provides novel silicon compounds, methods for making these novel silicon compounds, compositions comprising these novel silicon compounds attached to substrates, methods for attaching the novel silicon compounds to substrates and methods for using the compositions in a variety of chromatographic applications. Images(11) Claims(21)
1. A compound of structural Formula (II): or salts, solvates or hydrates thereof wherein: R1, R2 and R3 are independently alkyl, alkoxy, alkoxycarbonyl, alkylsulfonyloxy, amino, aryl, aryloxycarbonyl, arylsulfonyloxy, halo or hydroxyl, optionally substituted with one or more R14 groups, provided that at least one of R1, R2 and R3 are not alkyl, aryl or hydroxyl; L1 is alkyldiyl, heteroalkyldiyl, aryldiyl or heteroaryldiyl; Y is �C(O)N(R4)(R5), �N(R4)C(O)R7, �N(R4)S(O2)R7, �S(O)2N(R4)(R5), �OC(O)R7, �OC(O)N(R4)(R5), �N(R4)C(O)OR7, �N(R4)C(O)N(R5)(R6) or �N(R4)S(O2)N(R5)(R6); and R4, R5 and R6 are independently hydrogen, (C1-C6) alkyl optionally substituted with one or more hydroxy or cyano groups or (C5-C7) aryl optionally substituted with one or more hydroxy or cyano groups; R7 is (C1-C6) alkyl optionally substituted with one or more hydroxy or cyano groups or (C5-C7) aryl optionally substituted with one or more hydroxy or cyano groups and R14 is (C1-C6) alkyl; provided that one of R4, R5 or R6 is not hydrogen. 2. The compound of claim 1 having the structure 3. A composition comprising the compound of claim 1 covalently bonded to a substrate. 4. The composition of claim 3 in which the compound is covalently bonded to the substrate by reaction of one or more of R1, R2 and R3 with reactive groups on the substrate selected from the group consisting of silanol, alkoxysilane, halosilane or aminosilane. 5. The composition of claim 3 in which �SiR1(R2)(R3) is covalently bonded to another compound of claim 1 by reaction with reactive groups selected from the group consisting of silanol, alkoxysilane or halosilane on the other compound. 6. The composition of claim 3 of structural Formula (III): wherein R1, R3, L and Y are as defined in claim 1. 7. The composition of claim 3 having the structure: 8. A composition comprising the compound of claim 1 covalently bonded to a substrate and a compound of structural Formula (IV) covalently bonded to the substrate wherein: R8, R9, and R10 are independently alkyl, alkoxy, alkoxycarbonyl, alkylsulfonyloxy, amino aryl, aryloxycarbonyl, aryloxy, arylsulfonyloxy, halo or hydroxyl optionally substituted with one or more of the same or different R15 groups, provided that at least one of R1, R2 and R3 are not alkyl, aryl or hydroxyl; R15 is (C1-C6) alkyl; L2 is alkyldiyl, heteroalkyldiyl, aryldiyl or heteroaryldiyl; and W is an ionizable group. 9. The composition of claim 8 having structural Formula (V): 10. The composition of claim 8 having the structure: 11. The composition of claim 3 or claim 8 in which the substrate is a silica substrate. 12. The composition of claim 3 or claim 8 in which the silica substrate is silica gel. 13. The composition of claim 3 or claim 8 in which the substrate is glass, a sol-gel polymer or a hybrid sol-gel polymer. 14. The composition of claim 3 or claim 8 in a flow-through bed suitable for use in a reverse phase chromatographic medium. 15. The composition of claim 3 or claim 8 in a flow-through bed suitable for use in a multi mode chromatographic medium 16. A chromatographic method comprising flowing an aqueous liquid through a bed of separation medium comprising the composition of claim 3 or claim 8. 17. A method for the chromatographic separation of analytes in a liquid sample comprising flowing the liquid sample through medium comprising the composition of claim 3 or claim 8. 18. A method for simultaneous analysis of cationic, neutral and anionic surfactants in a liquid sample comprising flowing the liquid sample through medium comprising the composition of claim 3 or claim 8. 19. A chromatography column comprising the composition of claim 3 or claim 8 packed in a suitable housing. 20. A packing comprising the compound of claim 1 covalently bonded to a first substrate and a compound of structural Formula (IV) bonded to a second substrate wherein: R8, R9, and R10 are independently alkyl, alkoxy, alkoxycarbonyl, alkylsulfonyloxy, amino aryl, aryloxycarbonyl, aryloxy, arylsulfonyloxy, halo or hydroxyl, optionally substituted with one or more of the same or different R13 groups, provided that at least one of R1, R2 and R3 are not alkyl, aryl or hydroxyl; R13 is (C1-C6) alkyl; L2 is alkyldiyl, heteroalkyldiyl, aryldiyl or heteroaryldiyl; and W is an ionizable group. 21. The compound of claim 19 in which the first substrate and the second substrate are a silica substrate.
1. FIELD The present invention relates generally to novel silicon compounds, methods for making these novel silicon compounds, compositions comprising these novel silicon compounds attached to substrates, methods for attaching the novel silicon compounds to substrates and methods for using the compositions in a variety of chromatographic applications. 2. BACKGROUND Conventional reversed phase silica columns (e.g., ODS) are widely used as general-purpose stationary phases for chromatographic separations (Neue, �HPLC Columns�Theory, Technology, and Practice,� WILEY-VCH, New York, 1997, 183-203). However, some drawbacks, including, for example, �phase collapse� (i.e., dewetting) in highly aqueous environments, weak retention of ionic compounds and residual silanol activity which leads to peak tailing of basic analytes prevent employment of conventional reverse phase silica columns in certain applications. Polar-embedded phases improve the peak shape of basic analytes and enable operation of reverse phase HPLC columns in highly aqueous environments (O'Gara et al., LC-GC 2001, 19 (6):632-641). Commonly used polar groups include, for example, amides, ureas, ethers and carbamates. In general, polar-embedded phases provide superior peak shapes of basic analytes and are more compatible with highly aqueous environments when compared to general purpose reverse phases. Further, polar embedded phases often have selectivities which are substantially different from those exhibited by conventional C-18 packings. Surfactants are important components of a variety of consumer, industrial, agricultural and pharmaceutical products. Surfactant analysis is often complicated by the presence of mixtures which are difficult to resolve using conventional chromatography. Surfactants have been analyzed by liquid chromatography on reversed-phase columns (e.g., C18, C8, cyano, phenyl, etc.), normal phase columns, ion-exchange columns and size-exclusion columns (Schmitt, �Analysis of Surfactants,� 2nd edition, Marcel Dekker, Inc, New York, 2001, 197-292). C18 columns provide reasonable separation, peak efficiency and asymmetry, especially for anionic surfactants. However, the presence of underivatized silanols on silica-based reversed-phase columns often prevents satisfactory resolution of cationic surfactants. For example, C18 reversed phase columns fail to separate individual oligomers of polyethylene glycol (PEG) based surfactants. In addition, because of �de-wetting� caused by necessary usage of high aqueous mobile phases, conventional high-density C18 columns are unsuitable for analysis of highly hydrophilic hydrotopes, (e.g., sodium naphthalene sulfonate and xylene sulfonate). Despite the availability of a variety of HPLC columns to analyze a wide range of surfactants using a plurality of different conditions, no single column can be used to separate cationic, nonionic, and anionic surfactants in a single run using simple and volatile, mass spectroscopy compatible, mobile phases. Accordingly, what is needed are novel silane compounds which have both hydrophobic and polar functionality, substrates functionalized with these new silane compounds and the use of these novel functionalized substrates to simultaneously separate cationic, nonionic and anionic surfactants. 3. SUMMARY The present invention satisfies these and other needs by providing a new class of silane compounds, which have hydrophobic and polar functionality, substrates functionalized with these new silane compounds and the use of these novel functionalized substrates to simultaneously separate cationic, nonionic, and anionic surfactants. In one aspect, a compound described by Formula (I) is disclosed: or salts, solvates or hydrates thereof. The compound of Formula (I) has at least one activated silyl group (e.g., Si(OMe)3, �SiMe(OMe)2, �SiMe2(OMe), �Si(OEt)3, �SiMe(OEt)2, �SiMe2(OEt), �SiMe2NMe2, �SiCl3, etc.), at least one polar group (e.g., amide, sulfonamide, carbamate, urea, ester, etc.) and a short head chain (e.g., (C1-C6) alkyl) connected to the polar group. In another aspect, a compound of structural Formula (II) is provided: or salts, solvates or hydrates thereof wherein: R1, R2 and R3 are independently alkyl, alkoxy, alkoxycarbonyl, alkylsulfonyloxy, amino, aryl, aryloxycarbonyl, arylsulfonyloxy, halo or hydroxyl, optionally substituted with one or more R12 groups, provided that at least one of R1, R2 and R3 are not alkyl, aryl or hydroxyl; L1 is alkyldiyl, heteroalkyldiyl, aryldiyl or heteroaryldiyl; Y is �C(O)N(R4)(R5), �N(R4)C(O)R7, �N(R4)S(O2)R7, �S(O)2N(R4)(R5), �OC(O)R7, �OC(O)N(R4)(R5), �N(R4)C(O)OR7, �N(R4)C(O)N(R5)(R6) or �N(R4)S(O2)N(R5)(R6); and R4, R5 and R6 are independently hydrogen, (C1-C6) alkyl optionally substituted with one or more hydroxy or cyano groups or (C5-C7) aryl optionally substituted with one or more hydroxy or cyano groups; R7 is (C1-C6) alkyl optionally substituted with one or more hydroxy or cyano groups or (C5-C7) aryl optionally substituted with one or more hydroxy or cyano groups; and R14 is (C1-C6) alkyl; provided that one of R4, R5 or R6 is not hydrogen. In another aspect, a composition including a compound of Formula (II) covalently bonded to a substrate is provided. In some embodiments, the composition is in a flow-through bed suitable for use a reverse phase chromatographic medium. In still another aspect, a composition comprising the compound of structural Formula (II) covalently bonded to a substrate and a compound of structural Formula (IV) covalently bonded to the substrate is provided wherein: R8, R9, and R10 are independently alkyl, alkoxy, alkoxycarbonyl, alkylsulfonyloxy, amino aryl, aryloxycarbonyl, aryloxy, arylsulfonyloxy, halo or hydroxyl optionally substituted with one or more of the same or different R14 groups, provided that at least one of R1, R2 and R3 are not alkyl, aryl or hydroxyl; R15 is (C1-C6) alkyl; L2 is alkyldiyl, heteroalkyldiyl, aryldiyl or heteroaryldiyl; and W is an ionizable group. In still another aspect, a chromatographic method is provided. An aqueous liquid is flowed through a bed of separation medium, which includes either a composition containing a compound of Formula (II) covalently bonded to a substrate or a composition comprising the compound of structural Formula (II) covalently bonded to a substrate and a compound of structural Formula (IV) covalently bonded to the substrate. In still another aspect, a method for chromatographic separation of analytes in a liquid sample is provided. The liquid sample is flowed through medium, which includes a composition containing a compound of Formula (II) covalently bonded to a substrate or a composition comprising the compound of structural Formula (II) covalently bonded to a substrate and a compound of structural Formula (IV) covalently bonded to the substrate. In still another aspect, a method for simultaneous analysis of inorganic analytes and organic analytes in a liquid sample is provided. The liquid sample is flowed through medium, which includes a composition containing a compound of Formula (II) covalently bonded to a substrate or a composition of a compound of structural Formula (II) and a compound of structural Formula (IV) covalently bonded to a substrate.
4. BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 illustrates the synthesis of an amide of Formula (II); FIG. 2 illustrates the synthesis of amine derivatives of Formula (II); FIG. 3 illustrates the synthesis of alcohol derivatives of Formula (II); FIG. 4 illustrates synthesis of a compound of Formula (IV); FIG. 5 illustrates the separation of uracil, p-butyl benzoic acid and phenanthrene by a C8 column and a column packed with composition 27; FIG. 6 illustrates separation of a number of surfactants with and a column packed with composition 36; FIG. 7 illustrates the separation of Triton X-100 with a conventional C18 column and a column packed with composition 36; FIG. 8 illustrates the separation of a number of surfactants with a conventional C18 column and a column packed with composition 36; FIG. 9 illustrates the separation of lauryldimethylbenzyl ammonium chloride with a conventional C18 column and a column packed with composition 36; and FIG. 10 illustrates the separation of sodium xylene sulfonate with a conventional C18 column and a column packed with composition 36.
5. DETAILED DESCRIPTION 5.1 Definitions �Alkyl� by itself or as part of another substituent, refers to a saturated or unsaturated, branched, straight-chain or cyclic monovalent hydrocarbon radical derived by the removal of one hydrogen atom from a single carbon atom of a parent alkane, alkene or alkyne. Typical alkyl groups include, but are not limited to, methyl; ethyls such as ethanyl, ethenyl, ethynyl; propyls such as propan-1-yl, propan-2-yl, cyclopropan-1-yl, prop-1-en-1-yl, prop-1-en-2-yl, prop-2-en-1-yl(allyl), cycloprop-1-en-1-yl; cycloprop-2-en-1-yl, prop-1-yn-1-yl, prop-2-yn-1-yl, etc.; butyls such as butan-1-yl, butan-2-yl, 2-methyl-propan-1-yl, 2-methyl-propan-2-yl, cyclobutan-1-yl, but-1-en-1-yl, but-1-en-2-yl, 2-methyl-prop-1-en-1-yl, but-2-en-1-yl, but-2-en-2-yl, buta-1,3-dien-1-yl, buta-1,3-dien-2-yl, cyclobut-1-en-1-yl, cyclobut-1-en-3-yl, cyclobuta-1,3-dien-1-yl, but-1-yn-1-yl, but-1-yn-3-yl, but-3-yn-1-yl, etc.; and the like. The term �alkyl� is specifically intended to include groups having any degree or level of saturation, i.e., groups having exclusively single carbon-carbon bonds, groups having one or more double carbon-carbon bonds, groups having one or more triple carbon-carbon bonds and groups having mixtures of single, double and triple carbon-carbon bonds. Where a specific level of saturation is intended, the expressions �alkanyl,� �alkenyl,� and �alkynyl� are used. In some embodiments, an alkyl group comprises from 1 to 20 carbon atoms. In other embodiments, an alkyl group comprises from 1 to 10 carbon atoms. �Alkanyl� by itself or as part of another substituent, refers to a saturated branched, straight-chain or cyclic alkyl radical derived by the removal of one hydrogen atom from a single carbon atom of a parent alkane. Typical alkanyl groups include, but are not limited to, methanyl; ethanyl; propanyls such as propan-1-yl, propan-2-yl(isopropyl), cyclopropan-1-yl, etc.; butanyls such as butan-1-yl, butan-2-yl(sec-butyl), 2-methyl-propan-1-yl(isobutyl), 2-methyl-propan-2-yl (t-butyl), cyclobutan-1-yl, etc.; and the like. �Alkenyl� by itself or as part of another substituent, refers to an unsaturated branched, straight-chain or cyclic alkyl radical having at least one carbon-carbon double bond derived by the removal of one hydrogen atom from a single carbon atom of a parent alkene. The group may be in either the cis or trans conformation about the double bond(s). Typical alkenyl groups include, but are not limited to, ethenyl; propenyls such as prop-1-en-1-yl, prop-1-en-2-yl, prop-2-en-1-yl(allyl), prop-2-en-2-yl, cycloprop-1-en-1-yl, cycloprop-2-en-1-yl; butenyls such as but-1-en-1-yl, but-1-en-2-yl, 2-methyl-prop-1-en-1-yl, but-2-en-1-yl, but-2-en-1-yl, but-2-en-2-yl, buta-1,3-dien-1-yl, buta-1,3-dien-2-yl, cyclobut-1-en-1-yl, cyclobut-1-en-3-yl, cyclobuta-1,3-dien-1-yl, etc.; and the like. �Alkynyl� by itself or as part of another substituent, refers to an unsaturated branched, straight-chain or cyclic alkyl radical having at least one carbon-carbon triple bond derived by the removal of one hydrogen atom from a single carbon atom of a parent alkyne. Typical alkynyl groups include, but are not limited to, ethynyl; propynyls such as prop-1-yn-1-yl, prop-2-yn-1-yl, etc.; butynyls such as but-1-yn-1-yl, but-1-yn-3-yl, but-3-yn-1-yl, etc.; and the like. �Alkyldiyl� by itself or as part of another substituent, refers to a saturated or unsaturated, branched, straight-chain or cyclic divalent hydrocarbon group derived by the removal of one hydrogen atom from each of two different carbon atoms of a parent alkane, alkene or alkyne, or by the removal of two hydrogen atoms from a single carbon atom of a parent alkane, alkene or alkyne. The two monovalent radical centers or each valency of the divalent radical center can form bonds with the same or different atoms. Typical alkyldiyl groups include, but are not limited to methandiyl; ethyldiyls such as ethan-1,1-diyl, ethan-1,2-diyl, ethen-1,1-diyl, ethen-1,2-diyl; propyldiyls such as propan-1,1-diyl, propan-1,2-diyl, propan-2,2-diyl, propan-1,3-diyl, cyclopropan-1,1-diyl, cyclopropan-1,2-diyl, prop-1-en-1,1-diyl, prop-1-en-1,2-diyl, prop-2-en-1,2-diyl, prop-1-en-1,3-diyl, cycloprop-1-en-1,2-diyl, cycloprop-2-en-1,2-diyl, cycloprop-2-en-1,1-diyl, prop-1-yn-1,3-diyl, etc. butyldiyls such as, butan-1,1-diyl, butan-1,2-diyl, butan-1,3-diyl, butan-1,4-diyl, butan-2,2-diyl, 2-methyl-propan-1,1-diyl, 2-methyl-propan-1,2-diyl, cyclobutan-1,1-diyl; cyclobutan-1,2-diyl, cyclobutan-1,3-diyl, but-1-en-1,1-diyl, but-1-en-1,2-diyl, but-1-en-1,3-diyl, but-1-en-1,4-diyl, 2-methyl-prop-1-en-1,1-diyl, 2-methanylidene-propan-1,1-diyl, buta-1,3-dien-1,1-diyl, buta-1,3-dien-1,2-diyl, buta-1,3-dien-1,3-diyl, buta-1,3-dien-1,4-diyl, cyclobut-1-en-1,2-diyl, cyclobut-1-en-1,3-diyl, cyclobut-2-en-1,2-diyl, cyclobuta-1,3-dien-1,2-diyl, cyclobuta-1,3-dien-1,3-diyl, but-1-yn-1,3-diyl, but-1-yn-1,4-diyl, buta-1,3-diyn-1,4-diyl, etc.; and the like. Where specific levels of saturation are intended, the nomenclature alkanyldiyl, alkenyldiyl and/or alkynyldiyl is used. In some embodiments, the alkyldiyl group is (C1-C20) alkyldiyl. In other embodiments, the alkyldiyl group is (C1-C10) alkyldiyl. In still other embodiments, the alkyldiyl group is a saturated acyclic alkanyldiyl group in which the radical centers are at the terminal carbons, e.g., methandiyl(methano); ethan-1,2-diyl(ethano); propan-1,3-diyl (propano); butan-1,4-diyl(butano); and the like (also referred to as alkyleno, defined infra). �Alkyleno� by itself or as part of another substituent, refers to a straight-chain alkyldiyl group having two terminal monovalent radical centers derived by the removal of one hydrogen atom from each of the two terminal carbon atoms of straight-chain parent alkane, alkene or alkyne. Typical alkyleno groups include, but are not limited to, methano; ethylenos such as ethano, etheno, ethyno; propylenos such as propano, prop[1]eno, propa[1,2]dieno, prop[1]yno, etc.; butylenos such as butano, but[1]eno, but[2]eno, buta[1,3]dieno, but[1]yno, but[2]yno, but[1,3]diyno, etc.; and the like. Where specific levels of saturation are intended, the nomenclature alkano, alkeno and/or alkyno is used. In some embodiments, the alkyleno group is (C1-C20) alkyleno. In other embodiments, the alkyleno group is (C1-C10) alkyleno. In still other embodiments, the alkyleno group is a straight-chain saturated alkano groups, e.g., methano, ethano, propano, butano, and the like. �Alkylsulfonyloxy� by itself or as part of another substituent, refers to a radical �OS(O)2R30 where R30 represents an alkyl or cycloalkyl group as defined herein. �Alkoxy� by itself or as part of another substituent, refers to a radical �OR31 where R31 represents an alkyl or cycloalkyl group as defined herein. Representative examples include, but are not limited to, methoxy, ethoxy, propoxy, butoxy, cyclohexyloxy and the like. �Alkoxycarbonyl� by itself or as part of another substituent, refers to a radical �C(O)OR32 where R32 represents an alkyl or cycloalkyl group as defined herein. �Aryl� by itself or as part of another substituent, refers to a monovalent aromatic hydrocarbon radical derived by the removal of one hydrogen atom from a single carbon atom of a parent aromatic ring system. Typical aryl groups include, but are not limited to, groups derived from aceanthrylene, acenaphthylene, acephenanthrylene, anthracene, azulene, benzene, chrysene, coronene, fluoranthene, fluorene, hexacene, hexaphene, hexalene, as-indacene, s-indacene, indane, indene, naphthalene, octacene, octaphene, octalene, ovalene, penta-2,4-diene, pentacene, pentalene, pentaphene, perylene, phenalene, phenanthrene, picene, pleiadene, pyrene, pyranthrene, rubicene, triphenylene, trinaphthalene and the like. In some embodiments, an aryl group comprises from 5 to 20 carbon atoms. In other embodiments, an aryl group comprises from 5 to 12 carbon atoms. �Aryldiyl� by itself or as part of another substituent refers to a divalent hydrocarbon radical derived by the removal of one hydrogen atom from each of two different carbon atoms of a parent aromatic system or by removal of two hydrogen atoms from a single carbon atom of a parent aromatic ring system. The two monovalent radical centers or each valency of the divalent center can form bonds with the same or different atom(s). Typical aryldiyl groups include, but are not limited to, groups derived from aceanthrylene, acenaphthylene, acephenanthrylene, anthracene, azulene, benzene, chrysene, coronene, fluoranthene, fluorene, hexacene, hexaphene, hexalene, as-indacene, s-indacene, indane, indene, naphthalene, octacene, octaphene, octalene, ovalene, penta-2,4-diene, pentacene, pentalene, pentaphene, perylene, phenalene, phenanthrene, picene, pleiadene, pyrene, pyranthrene, rubicene, triphenylene, trinaphthalene and the like. In som embodiments, an aryldiyl group comprises from 5 to 20 carbon atoms. In other embodiments, an aryldiyl group comprises from 5 to 12 carbon atoms. �Aryloxycarbonyl� by itself or as part of another substituent, refers to a radical �C(O)OR33 where R33 represents an aryl group as defined herein. �Arylsulfonyloxy� by itself or as part of another substituent, refers to a radical �OS(O)2R35 where R35 represents an alkyl or cycloalkyl group as defined herein. �Cycloalkyl� by itself or as part of another substituent, refers to a saturated or unsaturated cyclic alkyl radical. Where a specific level of saturation is intended, the nomenclature �cycloalkanyl� or �cycloalkenyl� is used. Typical cycloalkyl groups include, but are not limited to, groups derived from cyclopropane, cyclobutane, cyclopentane, cyclohexane and the like. In some embodiments, the cycloalkyl group is (C3-C10) cycloalkyl. In other embodiments, the cycloalkyl group is (C3-C7) cycloalkyl. �Heteroalkyl, Heteroalkanyl, Heteroalkenyl, Heteroalkanyl, Heteroalkyldiyl and Heteroalkyleno� by themselves or as part of another substituent, refer to alkyl, alkanyl, alkenyl, alkynyl, alkyldiyl and alkyleno groups, respectively, in which one or more of the carbon atoms (and any associated hydrogen atoms) are each independently replaced with the same or different heteroatomic groups. Typical heteroatomic groups which can be included in these groups include, but are not limited to, �O�, �S�, �O�O�, �S�S�, �O�S�, �NR35R36�, ═N�N═, �N═N�, �N═N�NR37R38, �PR39�, �P(O)2�, �PR40�, �O�P(O)2�, �SO�, �SO2�, �SnR41R42� and the like, where R35, R36, R37, R38, R39, R40, R41 and R42 are independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl or substituted heteroarylalkyl. �Heteroaryl� by itself or as part of another substituent, refers to a monovalent heteroaromatic radical derived by the removal of one hydrogen atom from a single atom of a parent heteroaromatic ring system. Typical heteroaryl groups include, but are not limited to, groups derived from acridine, arsindole, carbazole, β-carboline, chromane, chromene, cinnoline, furan, imidazole, indazole, indole, indoline, indolizine, isobenzofuran, isochromene, isoindole, isoindoline, isoquinoline, isothiazole, isoxazole, naphthyridine, oxadiazole, oxazole, perimidine, phenanthridine, phenanthroline, phenazine, phthalazine, pteridine, purine, pyran, pyrazine, pyrazole, pyridazine, pyridine, pyrimidine, pyrrole, pyrrolizine, quinazoline, quinoline, quinolizine, quinoxaline, tetrazole, thiadiazole, thiazole, thiophene, triazole, xanthene, and the like. In some embodiments, the heteroaryl group is from 5-20 membered heteroaryl. In other embodiments, the heteroaryl group is from 5-10 membered heteroaryl. In still other embodiments, the heteroaryl groups are those derived from thiophene, pyrrole, benzothiophene, benzofuran, indole, pyridine, quinoline, imidazole, oxazole and pyrazine. �Heteroaryldiyl� by itself or as part of another substituent refers to a divalent radical derived by the removal of one hydrogen atom from each of two different carbon atoms of a parent heteroaromatic system or by removal of two hydrogen atoms from a single carbon atom of a parent aromatic ring system. The two monovalent radical centers or each valency of the divalent center can form bonds with the same or different atom(s). Typical heteroaryldiyl groups include, but are not limited to, groups derived from acridine, arsindole, carbazole, β-carboline, chromane, chromene, cinnoline, furan, imidazole, indazole, indole, indoline, indolizine, isobenzofuran, isochromene, isoindole, isoindoline, isoquinoline, isothiazole, isoxazole, naphthyridine, oxadiazole, oxazole, perimidine, phenanthridine, phenanthroline, phenazine, phthalazine, pteridine, purine, pyran, pyrazine, pyrazole, pyridazine, pyridine, pyrimidine, pyrrole, pyrrolizine, quinazoline, quinoline, quinolizine, quinoxaline, tetrazole, thiadiazole, thiazole, thiophene, triazole, xanthene, and the like. In some embodiments, a heteroaryldiyl group comprises from 5 to 20 carbon atoms. In other embodiments, a heteroaryldiyl group comprises from 5 to 12 carbon atoms. �Parent Aromatic Ring System� by itself or as part of another substituent, refers to an unsaturated cyclic or polycyclic ring system having a conjugated π electron system. Specifically included within the definition of �parent aromatic ring system� are fused ring systems in which one or more of the rings are aromatic and one or more of the rings are saturated or unsaturated, such as, for example, fluorene, indane, indene, phenalene, etc. Typical parent aromatic ring systems include, but are not limited to, aceanthrylene, acenaphthylene, acephenanthrylene, anthracene, azulene, benzene, chrysene, coronene, fluoranthene, fluorene, hexacene, hexaphene, hexalene, as-indacene, s-indacene, indane, indene, naphthalene, octacene, octaphene, octalene, ovalene, penta-2,4-diene, pentacene, pentalene, pentaphene, perylene, phenalene, phenanthrene, picene, pleiadene, pyrene, pyranthrene, rubicene, triphenylene, trinaphthalene and the like. �Parent Heteroaromatic Ring System� by itself or as part of another substituent, refers to a parent aromatic ring system in which one or more carbon atoms (and any associated hydrogen atoms) are independently replaced with the same or different heteroatom. Typical heteroatoms to replace the carbon atoms include, but are not limited to, N, P, O, S, Si, etc. Specifically included within the definition of �parent heteroaromatic ring systems� are fused ring systems in which one or more of the rings are aromatic and one or more of the rings are saturated or unsaturated, such as, for example, arsindole, benzodioxan, benzofuran, chromane, chromene, indole, indoline, xanthene, etc. Typical parent heteroaromatic ring systems include, but are not limited to, arsindole, carbazole, β-carboline, chromane, chromene, cinnoline, furan, imidazole, indazole, indole, indoline, indolizine, isobenzofuran, isochromene, isoindole, isoindoline, isoquinoline, isothiazole, isoxazole, naphthyridine, oxadiazole, oxazole, perimidine, phenanthridine, phenanthroline, phenazine, phthalazine, pteridine, purine, pyran, pyrazine, pyrazole, pyridazine, pyridine, pyrimidine, pyrrole, pyrrolizine, quinazoline, quinoline, quinolizine, quinoxaline, tetrazole, thiadiazole, thiazole, thiophene, triazole, xanthene, and the like. �Substituted� refers to a group in which one or more hydrogen atoms are independently replaced with the same or different substituent(s). Typical substituents include, but are not limited to, -M, �R60, �O−, ═O, �OR60, �SR60, �S−, ═S, �NR60R61, ═NR60�CF3, �CN, �OCN, �SCN, �NO, �NO2, ═N2, �N3, �S(O)2O−, �S(O)2OH, �S(O)2R60, �OS(O2)O−, �OS(O)2R60, �P(O)(O−)2, �P(O)(OR60)(O−), �OP(O)(OR60)(OR61), �C(O)R60, �C(S)R60, �C(O)OR60, �C(O)NR60R61, �C(O)O−, �C(S)OR60, �NR62C(O)NR60R61, �NR62C(S)NR60R61, �NR62C(NR63)NR60R61 and �C(NR62)NR60R61 where M is independently a halogen; R60, R61, R62 and R63 are independently hydrogen, alkyl, substituted alkyl, alkoxy, substituted alkoxy, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, aryl, substituted aryl, heteroaryl or substituted heteroaryl, or optionally R60 and R61 together with the nitrogen atom to which they are bonded form a cycloheteroalkyl or substituted cycloheteroalkyl ring; and R64 and R65 are independently hydrogen, alkyl, substituted alkyl, aryl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, aryl, substituted aryl, heteroaryl or substituted heteroaryl, or optionally R64 and R65 together with the nitrogen atom to which they are bonded form a cycloheteroalkyl or substituted cycloheteroalkyl ring. Preferably, substituents include -M, �R60, ═O, �OR60, �SR60, �S−, ═S, �NR60R61, ═NR60, �CF3, �CN, �OCN, �SCN, �NO, �NO2, ═N2, �N3, �S(O)2R60, �OS(O)O−, �OS(O)2R60, �P(O)(O−)2, �P(O)(OR60)(O−), �OP(O)(OR60)(OR61), �C(O)R60, �C(S)R60, �C(O)OR60, �C(O)NR60R61, �C(O)O−, �NR62C(O)NR60R61, more preferably, -M, �R60, ═O, �OR60, �SR60, �NR60R61, �CF3, �CN, �NO2, �S(O)2R60, �P(O)(OR60)(O−), �OP(O)(OR60)(OR61), �C(O)R60, �C(O)OR60, �C(O)NR60R61, �C(O)O−, most preferably, -M, �R60, ═O, �OR60, �SR60, �NR60R61, �CF3, �CN, �NO2, �S(O)2R60, �OP(O)(OR60)(OR61), �C(O)R60, C(O)OR60, �C(O)O−, where R60, R61 and R62 are as defined above. 5.2 Organosilanes and Substrates Thereof The present invention provides novel silane compounds which have both hydrophobic and ionic functionality. At one terminus of the novel silane compound is a silyl group, which can be covalently attached to a substrate. At the other end of the novel silane compound is a short head chain (e.g., (C1-C6) alkyl). The silyl group and the short head chain are connected via a linker joined to a polar group. The linkers may be alkyl, aryl, heteroaryl or heteroalkyl groups while the polar group may be amide, carbamate, urea, sulfonamide, etc. In one aspect, a compound described by Formula (I) is provided or salts, solvates or hydrates thereof. Compounds of Formula (I) have at least one activated silyl group, a head chain joined by a linker connected to a polar group. An �activated silyl group� refers to silicon moieties, which are capable of reacting with the surface of a substrate to form a covalent bond with the surface. For example, an activated silyl group can react with the surface of a silica substrate comprising surface Si�OH groups to create siloxane bonds between compounds of Formula (I) and the substrate. Exemplary activated silyl groups include, but are not limited to, �Si(OMe)3, �SiMe(OMe)2, �SiMe2(OMe), �Si(OEt)3, �SiMe(OEt)2, �SiMe2(OEt), �SiMe2NMe2 and �SiCl3. A �linker� refers to an alkyl, heteroalkyl, aryl or heteroaryl group. A �polar group� refers to an amide, sulfonamide, carbamate, urea, ester, etc. The linker in compounds of Formula (I) serve as a spacer between the activated silyl group and the polar group. In some embodiments, a compound of structural Formula (II) is provided: or salts, solvates or hydrates thereof wherein: R1, R2 and R3 are independently alkyl, alkoxy, alkoxycarbonyl, alkylsulfonyloxy, amino, aryl, aryloxycarbonyl, arylsulfonyloxy, halo or hydroxyl, optionally substituted with one or more R14 groups, provided that at least one of R1, R2 and R3 are not alkyl, aryl or hydroxyl; L1 is alkyldiyl, heteroalkyldiyl, aryldiyl or heteroaryldiyl; Y is �C(O)N(R4)(R5), �N(R4)C(O)R7, �N(R4)S(O2)R7, �S(O)2N(R4)(R5), �OC(O)R7, �OC(O)N(R4)(R5), �N(R4)C(O)OR7, �N(R4)C(O)N(R5)(R6) or �N(R4)S(O2)N(R5)(R6); and R4, R5 and R6 are independently hydrogen, (C1-C6) alkyl optionally substituted with one or more hydroxy or cyano groups or (C5-C7) aryl optionally substituted with one or more hydroxy or cyano groups; R7 is (C1-C6) alkyl optionally substituted with one or more hydroxy or cyano groups or (C5-C7) aryl optionally substituted with one or more hydroxy or cyano groups and R14 is (C1-C6) alkyl; provided that one of R4, R5 or R6 is not hydrogen. In some embodiments, R1, R2 and R3 are independently alkyl, alkoxy or halo. In other embodiments, R1, R2 and R3 are alkoxy. In still other embodiments, R1, R2 and R3 are alkyl or alkoxy. In still other embodiments, R1, R2 and R3 are ethoxy or methyl. In some embodiments, L1 is alkyldiyl. In other embodiments, L1 is alkanyldiyl. In still other embodiments, L1 is alkyleno. In still other embodiments, L1 is (C6-C20) alkanyleno. In still other embodiments, L1 is (C8-C15) alkanyleno. In still other embodiments, L1 is (C10-C11) alkanyleno. In some embodiments, R4, R5 and R6 are independently hydrogen, alkyl, or aryl. In other embodiments, R4, R5 and R6 are independently alkyl, or aryl. In still other embodiments, R4, R5 and R6 are independently methyl or phenyl. In still other embodiments, R4, R5 and R6 are methyl. In some embodiments, R1, R2 and R3 are independently alkyl, alkoxy or halo, L1 is alkyldiyl and R4, R5 and R6 are independently hydrogen, alkyl, or aryl. In other embodiments, R1, R2 and R3 are alkyl or alkoxy, L1 is (C8-C15) alkanyleno and R4, R5 and R6 are independently alkyl, or aryl. In still other embodiments, R1, R2 and R3 are ethoxy or methyl, L1 is (C10-C11) alkanyleno and R4, R5 and R6 are independently methyl or phenyl. In some embodiments, R4, R5 and R6 are methyl. In other embodiments, R5 is phenyl. In some embodiments, the compounds of Formula (II) have the structure: Exemplary methods of synthesizing compounds described herein are presented in Schemes 1-4, infra. Starting materials useful for preparing compounds described herein are commercially available or can be prepared by well-known synthetic methods. Other methods for synthesis of the compounds described herein will be readily apparent to the skilled artisan. Accordingly, the methods presented in Schemes 1-4 herein are illustrative rather than comprehensive. Referring now to FIG. 1, 10-undecanoyl chloride 10 is reacted with dimethylamine 11 to provide amide 12. Amide 12 is then hydrosilylated with silane 13 in presence of a platinum catalyst to yield compound 1. Referring now to FIG. 2, the imine of undecylenic aldehyde 14 is formed upon treatment with methylamine 15. The imine 16 is reduced with sodium borohydride 17 to provide amine 18 which is hydrosilylated with silane 13 in the presence of a platinum catalyst to provide the mono-methylated amine 19. Amine 19 may be reacted with acetyl chloride 20, benzenesulfonyl chloride 21, ethyl chloroformate 22, N,N-dimethylcarbamyl chloride 23 or N,N-dimethylsulphamoyl chloride 24 to provide silicon compounds 3, 4, 5, 6 and 7, respectively. Referring now to FIG. 3, 10-undecen-1-ol 25 is hydrosilylated with silane 13 in the presence of a platinum catalyst to provide silyl alcohol 26. Acylation of silyl alcohol 26 with acetyl chloride 20 or N,N-dimethylcarbamyl chloride 23, provides silicon compounds 8 and 9, respectively. Referring now to FIG. 4, bromide 37 is displaced with dimethylamine 11 to provide the amine 38 which is then hydrosilated with silane in the presence of platinum catalyst to yield the silylamine 39. Compound 39 may be used as the ionizable component of a mixed mode chromatography support. Those of skill in the art will appreciate that the synthetic strategies disclosed, supra, may be readily adapted to make silanes with aryl, heteroaryl and heteroalkyl linkers by varying the starting amine or acyl chloride or alkyl halide. Further, diverse methods are known to those of skill in the art to accomplish the transformations above (or equivalents thereof) and may be found in any compendia of organic synthesis (see e.g., Harrison et al., �Compendium of Synthetic Organic Methods�, Vols. 1-8 (John Wiley and Sons, 1971-1996); �Beilstein Handbook of Organic Chemistry,� Beilstein Institute of Organic Chemistry, Frankfurt, Germany; Feiser et al., �Reagents for Organic Synthesis,� Volumes 1-17, Wiley Interscience; Trost et al., �Comprehensive Organic Synthesis,� Pergamon Press, 1991; �Theilheimer's Synthetic Methods of Organic Chemistry,� Volumes 1-45, Karger, 1991; March, �Advanced Organic Chemistry,� Wiley Interscience, 1991; Larock �Comprehensive Organic Transformations,� VCH Publishers, 1989; and Paquette, �Encyclopedia of Reagents for Organic Synthesis,� John Wiley & Sons, 1995). The compounds disclosed, supra, may be reacted with substrates to form functionalized substrates, which can be used in a wide range of different applications. The compounds disclosed, supra, incorporate both hydrophobic and polar sites in one molecular structure and have reproducible surface chemistries in reactions with substrate surfaces. In some embodiments, a compound of structural Formula (II) is covalently bonded to a substrate. In other embodiments, the compound of structural Formula (II) is covalently bonded to the substrate by reaction of one or more of R1, R2 and R3 groups with reactive groups on the substrate such, for example, silanol, alkoxysilane, halosilane or aminosilane. In some embodiments, a compound of structural Formula (II) is covalently bonded through the SiR1(R2)(R3) group, to another compound of structural Formula (II) by reaction with reactive groups selected from the group consisting of silanol, alkoxysilane or halosilane on the other compound. In this embodiment, the two compounds are both covalently bonded to the substrate. In some embodiments, compositions of structural Formula (III) are provided where R1, R3, L and Y are as defined, supra. In other embodiments, compositions having the following structures are provided: In still other embodiments, compositions of at least one compound of structural Formula (II) and at least one compound of structural Formula (IV) covalently bonded to a substrate are provided where R8, R9, and R10 are independently alkyl, alkoxy, alkoxycarbonyl, alkylsulfonyloxy, amino aryl, aryloxycarbonyl, aryloxy, arylsulfonyloxy, halo or hydroxyl optionally substituted with one or more of the same or different R15 groups, provided that at least one of R1, R2 and R3 are not alkyl, aryl or hydroxyl; R15 is (C1-C6) alkyl; L2 is alkyldiyl, heteroalkyldiyl, aryldiyl or heteroaryldiyl; and W is an ionizable group. In other embodiments, a composition of structural Formula (V) is provided where R1, R3, L1, L2, Y and W are as defined, supra. In some embodiments, R8, R9 and R10 are independently alkyl, alkoxy or halo. In other embodiments, R8, R9 and R10 are alkoxy. In still other embodiments, R8, R9 and R10 are alkyl or alkoxy. In still other embodiments, R8, R9 and R10 are ethoxy or methyl. In some embodiments, L2 is alkydiyl. In other embodiments, L2 is alkanyldiyl. In still other embodiments, L2 is alkyleno. In still other embodiments, L2 is (C6-C20) alkanyleno. In still other embodiments, L2 is (C8-C15) alkanyleno. In still other embodiments, L2 is (C10-C11) alkanyleno. In some embodiments, W is �CO2 −, �SO3 −, �P(O)(OR11)O�, �NR11R12, or �N+R11R12R13, where R11, R12, R13 are independently hydrogen or (C1-C6) alkyl. In other embodiments, W is �NR11R12, or �N+R11R12R13 wherein R11, R12 and R13 are methyl. In some embodiments, R1, R2, R3, R8, R9 and R10 are independently alkyl, alkoxy or halo, L1 and L2 are alkyldiyl, R4, R5 and R6 are independently hydrogen, alkyl, or aryl and W is �NR11R12, or �N+R11R12R13 where R11, R12 and R13 are independently (C1-C6) alkyl. In some embodiments, R1, R2, R3, R8, R9 and R10 are alkyl or alkoxy, L1 and L2 are (C8-C15) alkanyleno, R4, R5 and R6 are independently alkyl, or aryl and W is �NR11R12, or �N+R11R12R13 where R11, R12 and R13 are independently (C1-C6) alkyl. In other embodiments, R1, R2, R3, R8, R9 and R10 are ethoxy or methyl, L1 and L2 are (C10-C11) alkanyleno, R4, R5 and R6 are independently methyl or phenyl and W is �NR11R12, or �N+R11R12R13 where R11, R12 and R13 are methyl. In a more specific embodiment, R4, R5 and R6 are methyl. In another more specific embodiment, R5 is phenyl. In some embodiments, a compound of Formula (II) and the compound of Formula (IV) are covalently bonded to the substrate by reaction of one or more of R1, R2 and R3 and one or more of R8, R9 and R10 with reactive groups on the substrate selected from the group consisting of silanol, alkoxysilane, halosilane or aminosilane. In other embodiments, R2 and R9 are �OEt. In still other embodiments, a composition where the compound of Formula (II) is and the compound of Formula (IV) is is provided. In still other embodiments a composition of the following structure is provided: In some embodiments, compounds of Formulae (I) and (II) are covalently attached to substrates as shown, supra. In these embodiments, the polar group is disposed from the surface of the substrate, which may improve hydrolytic stability of the functionalized substrate. Compounds of Formulae (I) and (II) can be attached to substrates (e.g., silica) to provide a functionalized stationary phase for various chromatographic separations such as reversed phase separations of surfactants. Further, compounds of Formulae (I) and (II) may be mixed with silyl ligands containing one or more ion exchange functionality (e.g., compounds of Formula (IV) prior to reaction with the substrate to provide mixed mode substrates of varying selectivity that also can be used for reversed phase separations of surfactants. Compounds of Formulae (I), (II) and (IV) may be covalently bound to a substrate by reaction of R1, R2 or R3 of the Si functionality with reactive groups on the substrate selected from the group consisting of silanol, alkoxysilane, halosilane and aminosilane moieties. In some embodiments, compounds of Formulae (I), (II) and (IV) which are covalently bonded to a substrate may be cross linked to one or more compounds of Formulae (I), (II) or (IV) by reaction with reactive groups selected from the group consisting of silanol, alkoxysilane or halosilane on other compound of Formulae (I), (II) or (IV). Compounds of Formulae (I), (II) and (IV) can be covalently attached to a variety of substrates. Exemplary substrates include materials that have a functional group that can react with activated silyl groups in compounds of Formulae (I), (II) and (IV). Thus, compounds of Formulae (I), (II) and (IV) can be attached, for example, to silica based materials such as glass surfaces, or the surfaces of other silicon oxide, titanium oxide, germanium oxide, zirconium oxide and aluminum oxide based materials; and also to the surfaces of various carbonized materials, metals, crosslinked and non-crosslinked polymers, which contain suitable functional groups for reacting with activated silyl groups. Examples of suitable functional groups include silanols, alkoxysilanes, titanium hydroxides, zirconium hydroxides, etc. Compounds of Formulae (I), (II) and (IV) can also be incorporated into polymeric or sol-gel networks by utilizing reactive silicon functionalities. Compounds of Formulae (I), (II) and (IV) containing polymerizable groups or groups that can be converted into radicals and/or ion-radicals and/or ions, can be used for making polymeric materials and for surface grafting, by utilizing those groups and/or reactive silicon functionalities. The resulting materials can be applied for a development of adsorbents, membranes, filters, microfluidic devices, microchips, and functionalized surfaces for various types of separation, detection, and analysis. In some embodiments, mono- and multi-layered surfaces are prepared by treating silica substrates with compounds of Formulae (I), (II) and/or (IV). Compounds of Formulae (I), (II) and/or (IV) can be covalently attached to a variety of substrates, such as silica gel, zirconia, hybrid sol-gel/polymers or glass plates. Suitable silica gels comprise non-porous, or porous silica particles of different pore sizes, preferably from 20 Å to 3000 Å and more preferably, from 60 Å to 2000 Å; and of different particle sizes, preferably, from 0.2 um to 1000 um, and more preferably, from 2 um to 50 um. The attachment reaction can be carried out in a slurry of silica gel in an inert solvent, such as toluene, at elevated temperature. Water, acid or base catalyst can be applied to enhance the surface coverage, depending on the type of properties desired for the separation media. Alternatively, an aminosilane compound, such as bis(trimethoxysilylpropyl)amine can be used for modifying underivatized silica gel by incorporating the reactive amino group onto a surface. Then, a reagent, such as acyl chloride, carbamyl chloride, sulfonyl chloride, or isocyanate, containing a proper functional group, can be reacted with the aminated silica gel to form the corresponding bonded phase. The compositions described herein may be used as packing for chromatography columns. The packing may be particles, monoliths (i.e., material containing pores) or packed bed resins which are loaded into a housing suitable for a chromatography column. Also provided is a packing of a compound of structural Formula (I) covalently bonded to a substrate and a compound of structural Formula (IV) bonded to another substrate. In some embodiments, the substrates are silica substrates. The compositions described herein may be used to resolve a variety of compounds. Generally, the compositions described herein may be used to separate surfactants. The compositions described herein may also be used, in some situations to resolve a mixture including cationic surfactants, anionic surfactants and neutral surfactants in a single chromatographic run. This invention provides simple and versatile approaches to produce a variety of novel solid supports with excellent hydrolytic stability. The method of synthesis allows for efficient incorporation of different functionalities onto the surfaces of the substrates and silica substrates, in particular. The resulting materials can be applied for development of adsorbents, membranes, filters, microfluidic devices, microchips, and functionalized surfaces for various types of separation, detection and analysis. 6. EXAMPLES The following examples are provided by way of illustration only and not by way of limitation. Those of skill in the art will readily recognize a variety of noncritical parameters that could be changed or modified to yield essentially similar results. 6.1 Preparation of Compound 1 Dimethylamine was mixed with an excess of triethylamine (2.0 eq.) in anhydrous CH2Cl2 and kept at between about 0� C. and about 5� C. for 20 min. Then, a solution of 10-undecenoyl chloride (1.0 eq.) in CH2Cl2 was added dropwise and the mixture was stirred at ambient temperature for 12 h. The reaction mixture was washed with water, dried over Na2SO4 and the solvent was removed in vacuo to yield the dimethylamide of 10-undecenoic acid. Excess dimethylethoxysilane (10 eq.) was added to the amide followed by addition of a solution of catalyst (0.1 mol %), (e.g., hexachloroplatinic acid in a minimum amount of ethanol). After stirring at 50� C. for 24 h, the silane and solvent were removed in vacuo to provide compound 1. 6.2 Example 2 Preparation of Compounds 3, 4, 5, 6 and 7 To a solution of 10-undecylenic aldehyde (1 eq.) in anhydrous methanol was added excess methylamine in anhydrous methanol (3 eq.). After 6 h at ambient temperature, the reaction mixture was filtered followed by concentration in vacuo to give imine 16. Then imine 16 was reduced with sodium borohydride (6 eq.) in methanol at ambient temperature for 24 h. After removal of all volatiles in vacuo, amine 18 was obtained by partitioning the residue between Et2O and H2O, drying over Na2SO4 and concentrating in vacuo. Then excess dimethylethoxysilane (10 eq.) was added to compound 18 followed by addition of a solution of catalyst (0.1 mol %), (e.g., hexachloroplatinic acid in a minimum amount of ethanol). After stirring at 50� C. for 24 h, the silane and solvent were removed in vacuo to provide silyl compound 19. Compound 19 was mixed with excess triethylamine (2.0 eq.) in anhydrous CH2Cl2 and kept at between about 0� C. and about 5� C. for 20 min. A solution of acetyl chloride (1.2 equiv) in anhydrous CH2Cl2 was then added dropwise and the mixture was stirred at ambient temperature for 12 h. All volatiles were removed in vacuo and hexanes were added to precipitate triethylammonium chloride salt. Compound 3 was obtained after filtration and removal of solvent in vacuo. Similarly, compounds 4, 5, 6 and 7 can be prepared by reacting compound 19 with sulfonyl chloride, ethyl chloroformate, N,N-dimethylcarbamyl chloride and N, N-dimethylsulphamoyl chloride, respectively. 6.3 Example 3 Preparation of Compounds 8 and 9 Excess dimethylethoxysilane (10 equiv) was added to 10-undecen-1-ol (25) followed by addition of a solution of catalyst (0.1 mol %), (e.g., hexachloroplatinic acid in a minimum amount of ethanol). After stirring at 50� C. for 24 h, the silane and solvent were removed in vacuo to provide silyl compound 26. Compound 26 was then mixed with excess triethylamine (2.0 eq.) in anhydrous CH2Cl2 and kept at between about 0� C. and about 5� C. for 20 min. Then, a solution of acetyl chloride (1.2 eq.) in anhydrous CH2Cl2 was added dropwise and the mixture stirred at ambient temperature for 12 h. All volatiles were removed in vacuo and hexanes were added to precipitate triethylammonium chloride salt. Compound 8 was obtained after filtration and concentration in vacuo. Similarly compound 9 can be prepared by reacting compound 26 with N, N-dimethylcarbamyl chloride. 6.4 Example 4 Preparation of Compound 39 A 5� C. solution of 11-bromo-1-undecene in THF was added dropwise to a solution of dimethylamine (10 eq.) in THF and stirred at ambient temperature for 12 h. The volatiles were removed in vacuo and the residue was partitioned between CH2Cl2 and H2O, dried over Na2SO4 followed by removal of solvent in vacuo to provide 38. Excess dimethylethoxysilane (10 eq.) was added to compound 38 followed by addition of a solution of catalyst (0.1 mol %), (e.g., hexachloroplatinic acid in a minimum amount of ethanol). After stirring at 50� C. for 24 h, the silane and solvent were removed in vacuo to provide silyl compound 39. 6.5 Example 5 Synthesis of Compositions 27, 28, 29, 30, 31, 32, 33, 34 and 35 Compounds 27, 28, 29, 30, 31, 32, 33, 34, or 35 in an inert solvent (e.g., toluene at elevated temperature) were reacted with a slurry of selected raw silica gel with the following physical properties: average particle size, 5.0 μm; specific surface area, 300 m2/g; mean pore size, 120 Å; pore volume, 1.00 mL/g. The addition of water, acid or base catalyst can be applied to control the surface coverage. After a certain period of time (from 3 h to 6 days), the reaction slurry was filtered, washed with acetone, and dried in vacuum oven at 50� C. for 5 h. A proper end-capping reagent, such as a trialkylsilyl chloride, may also be required to produce a packing material for chromatographic separations. 6.6 Example 6 Synthesis of Composition 36 Compounds 27 and 39 were mixed in appropriate ratios in an inert solvent such as toluene at elevated temperature. Then raw silica with the characteristics described in Example 6 was added to the above mixture to form a reaction slurry which was kept elevated temperature for 3 days. The reaction slurry was filtered, washed with acetone, and dried in vacuum oven at 50� C. for 5 h to give functionalized silica of composition 36. A proper end-capping reagent, such as a trialkylsilyl chloride, may also be required to produce a packing material for the reversed-phase chromatographic separation. 6.7 Example 7 Polarity Test HPLC chromatography of a test mixture containing uracil, p-butyl benzoic acid and phenanthrene on composition 27 packed into 4.6�150 mm stainless steel tubes using traditional high pressure slurry techniques yielded the results illustrated in FIG. 1. The mixture (injection volume of about 5 μL) was eluted with CH3CN/25 mM phosphate buffer at about pH 3.2 at a flow rate of about 1 mL/min at about 30� C. and was detected at 210 nm. For comparison, a C8 column of the same column dimension and prepared using the same silica substrate was also used in chromatography of the test mixture. FIG. 1 illustrates the high polarity of composition 27, since the relative retention of the polar compound p-butyl benzoic acid to neutral compound phenanthrene is higher on composition 27 than that on C8 column despite that fact that the latter has lower carbon content. Enhancement of polarity may be due to the placement of polar group at the end of the ligand furthest disposed from the silica surface. 6.8 Example 8 Separation of Cationic, Nonionic and Anionic Surfactants HPLC chromatography of a test mixture containing 7 common surfactants including two cationic surfactants (lauryldimethylbenzyl ammonium chloride and octylphenoxyethoxyethyl dimethylbenzyl ammonium chloride), four anionic surfactants (sodium salts of xylene sulfonate, dodecylbenzene sulfonate, decyl sulfate, and dodecyl sulfate) and one nonionic surfactant (Triton X-100), on composition 36 packed into 4.6�150 mm stainless steel tubes using traditional high pressure slurry techniques yielded the results illustrated in FIG. 6. The test mixture (injection volume of about 25 μL) was eluted with, CH3CN (A) and 0.1 M NH4OAc at about pH 5.8 (B) mobile phases using a gradient method (25% to 85% A in 30 min, then keep at 85% A for additional 10 min), at a flow rate of about 1 mL/min, at about 30� C. and was detected with evaporative light scattering detection (ELS). 6.9 Example 9 Chromatographic Comparison: Analysis of Ethoxylated Surfactants As shown in FIG. 7, a column packed with composition 36 was compared with a conventional C18 column of the same column dimension (5 μm, in 4.6�150 mm stainless steel tubes) in analysis of an ethoxylated nonionic surfactant Triton X-100. The sample (injection volume of about 10 μL) was eluted with CH3CN and 0.1 M NH4OAc at about pH 5.4 (isocratic mobile phases) at a flow rate of about 1 mL/min, at about 30� C. and was detected by UV at 225 nm. 6.10 Example 10 Chromatographic Comparison: Selectivity HPLC chromatography of a test mixture containing 5 common surfactants including four anionic surfactants (sodium salts of xylene sulfonate, dodecylbenzene sulfonate, decyl sulfate and dodecyl sulfate) and one nonionic surfactant (Triton X-100), on composition 36 packed into 4.6�150 mm stainless steel tubes using traditional high pressure slurry techniques yielded the results illustrated in FIG. 8. The test mixture (injection volume of about 25 μL) was eluted with CH3CN (A) and 0.1 M NH4OAc at about pH 5.8 (B) mobile phases using a gradient method (25% to 85% A in 30 min, then keep at 85% A for additional 10 min) at a flow rate of about 1 mL/min at about 30� C. and detected with an evaporative light scatting detector. For comparison, the same test mixture was also chromatographed on a C18 column of the same column dimension. 6.11 Example 11 Chromatographic Comparison: Analysis of Cationic Surfactants As shown in FIG. 9, a column packed with composition 36 was compared with a conventional C18 column of the same column dimension (5 μm, in 4.6�150 mm stainless steel tubes) in analyzing the cationic surfactant lauryldimethylbenzyl ammonium chloride. The sample (injection volume of about 5 μL) was eluted with CH3CN and 0.1 M NH4OAc at pH 5.4 (isocratic mobile phases) at a flow rate of about 1 mL/min at about 30� C. and was detected by ELS. The column packed with composition 36 exhibits superior peak shape over the C18 column. 6.12 Example 12 Chromatographic Comparison: Analysis of Sodium Xylene Sulfonate As shown in FIG. 10, a column packed with composition 36 was compared with a conventional C18 column of the same column dimension (5 μm, in 4.6�150 mm stainless steel tubes) in analyzing the highly hydrophilic surfactant, sodium xylene sulfonate. The sample (injection volume of about 5 μL) was eluted with, CH3CN/0.1 M NH4OAc, about pH 5.4 v/v 30/70 (isocratic mobile phases) at a flow rate of about 1 mL/min, at about 30� C. and detected by UV at about 225 nm. The column packed with composition 36 exhibits excellent resolution among the isomers with decent retention times. Although the foregoing invention has been described in some detail by way of illustration and example for purposes of clarity of understanding, it will be readily apparent to one of ordinary skill in the art in light of the teachings of this invention that certain changes and modifications may be made thereto without departing from the spirit or scope of the appended claims. All publications and patent documents cited in this specification are herein incorporated by reference in their entirety. Referenced byCiting PatentFiling datePublication dateApplicantTitleUS7402243 *Sep 10, 2004Jul 22, 2008Dionex CorporationOrganosilanes and substrate bonded with sameUS7557232May 25, 2007Jul 7, 2009Dionex CorporationReaction product of 1,2-epoxy-9-decene and dimethylethoxysilane, for example; can be used in either hydrophilic (HILIC) mode, in which the mobile phase includes a high percentage of an organic solvent, or in reversed phase modeUS8182679Apr 28, 2008May 22, 2012Dionex CorporationOrganosilanes and substrate bonded with sameUS8425778May 4, 2012Apr 23, 2013Dionex CorporationOrganosilanes and substrate bonded with sameUS8680311Nov 6, 2007Mar 25, 2014Waters Technologies CorporationMonolithic electrokinetic pump fabricationUS20110284465 *May 19, 2011Nov 24, 2011Dionex CorporationFunctionalized substrates with aromatic stacking propertiesEP2783749A2 *Mar 17, 2014Oct 1, 2014Dionex CorporationEpoxy chemistry derived materials as mixed mode chromatography media, method for their synthesis and useWO2008136854A2 *Nov 6, 2007Nov 13, 2008Edouard S P BouvierMonolithic electrokinetic pump fabrication* Cited by examinerClassifications U.S. Classification210/656, 210/198.2, 422/70, 210/502.1International ClassificationB01D15/08Cooperative ClassificationB01J20/286, B01J20/287, B01J20/3257, C07B2200/11, C07F7/1844, B01J20/3259, B01J20/3261European ClassificationC07F7/18C4DLegal EventsDateCodeEventDescriptionJun 14, 2012FPAYFee paymentYear of fee payment: 4Aug 31, 2010CCCertificate of correctionMay 25, 2005ASAssignmentOwner name: DIONEX CORPORATION, CALIFORNIAFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:LIU, XIAODONG;POHL, CHRISTOPHER A.;REEL/FRAME:016594/0564Effective date: 20050505RotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS Patent Services


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9781480341036 - Alibris
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Reinventing Metal: the True Story of Pantera and the Tragically Short Life of Dimebag Darrell: an Unauthorized Biography
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Patent US4168331 - Process for preparing resin impregnated substrates for use in preparing ... - Google Patents
The preparation of substrates impregnated with epoxy resins and curing agents therefor is improved by employing as the epoxy resin one which has been prepared by reacting a low equivalent weight epoxy resin such as a diglycidyl ether of bisphenol A with a dihydric phenolic compound such as tetrabromo...http://www.google.com/patents/US4168331?utm_source=gb-gplus-sharePatent US4168331 - Process for preparing resin impregnated substrates for use in preparing electrical laminates
Publication number US4168331 A
Application number US 05/930,640
Publication number 05930640, 930640, US 4168331 A, US 4168331A, US-A-4168331, US4168331 A, US4168331A
Inventors William Davis
Process for preparing resin impregnated substrates for use in preparing electrical laminates
US 4168331 A
The preparation of substrates impregnated with epoxy resins and curing agents therefor is improved by employing as the epoxy resin one which has been prepared by reacting a low equivalent weight epoxy resin such as a diglycidyl ether of bisphenol A with a dihydric phenolic compound such as tetrabromo bisphenol A in the presence of a quaternary ammonium hydroxide such as tetramethyl ammonium hydroxide.
1. In a process for preparing resin impregnated substrates for use in preparing electrical laminates which process comprises:
(A) an epoxy resin having an epoxide equivalent weight of from about 300 to about 600, which has been prepared by reacting
(1) a glycidyl ether of a dihydric phenol having an average of more than one epoxide group per molecule and an epoxide equivalent weight (EEW) of from about 156 to about 400, with
(3) a catalyst for effecting the reaction between 1 and 2;
(C) a solvent system for Components A and B; and
(II) heating the resultant impregnated substrate to B-stage the resin and remove the solvent system; the improvement which comprises employing as the catalyst a quaternary ammonium hydroxide.
2. The process of claim 1 wherein Component (A-1) has an EEW of from about 170 to about 200 and Components (A-1) and (A-2) are employed in quantities such that the phenolic hydroxyl to epoxide equivalent ratio is from about 0.2:1 to about 0.35:1.
3. The process of claim 2 wherein Component (A-1) has an EEW of from about 180 to about 195 and Components (A-1) and (A-2)are employed in quantities such that the phenolic hydroxyl to epoxide equivalent ratio is from about 0.24:1 to about 0.31:1.
4. The process of claim 3 wherein Component (A-1) is a diglycidyl ether of bisphenol A, Component (A-2) is tetrabromo bisphenol A and Component (A-3) is a quaternary ammonium hydroxide represented by the formula ##STR5## where is R1,R2, R3, and R4 are independently a hydrocarbon group having from 1 to about 10 carbon atoms.
5. The process of claim 4 wherein Component (A-3) is tetramethyl ammonium hydroxide.
6. The process of claim 4 wherein Component (A-3) is benzyl trimethyl ammonium hydroxide.
7. A resin impregnated substrate prepared by the process of claims 1, 2, 3, 4, 5 or 6.
Electrical laminates have been prepared from substrates impregnated with epoxy resins and curing agents therefor employing as the epoxy resin one which has been prepared from a diglycidyl ether and a dihydric phenolic compound employing as a catalyst a phosphonium compound. Electrical laminates when prepared from such substrates often fail the pressure cooker-solder test.
It has now been unexpectedly discovered that when the phosphonium catalyst is replaced by an ammonium hydroxide catalyst that the resultant electrical laminates pass the pressure cooker-solder test and the glass transition temperature is increased as well as an improvement in one or more physical properties of the electrical laminates.
The present invention pertains to an improvement in a process for preparing resin impregnated substrates for use in preparing electrical laminates which comprises:
(ii) heating the resultant impreganted substrate to B-stage the resin and remove the solvent system; the improvement which comprises employing as the catalyst Component (A-3) a quaternary ammonium hydroxide. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
Suitable glycidyl ethers of a dihydric phenol which can be employed in the present invention include those represented by the formula ##STR1## wherein A is a divalent hydrocarbon group having from 1 to about 8 carbon atoms, --S--, --S--S--, --O--, ##STR2## each X is independently hydrogen, chlorine or bromine; x has a value of zero or one and n has a value such that the EEW is from about 156 to about 400 preferably from about 177 to about 190.
The dihydric phenol and the glycidyl ether of a dihydric phenol are employed in quantities such that the phenolic OH:epoxide equivalent ratio is from about 0.2:1 to about 0.35:1 preferably from about 0.24:1 to about 0.31:1.
Suitable quaternary ammonium hydroxides include, for example, those represented by the formula ##STR4## wherein each R1, R2, R3, and R4 are independently a hydrocarbon group having from 1 to about 10 carbon atoms. Particularly suitable quaternary ammonium hydroxides include, for example, tetramethyl ammonium hydroxide and benzyl trimethyl ammonium hydroxide,
The quaternary ammonium hydroxide catalyst is employed in quantites of from about 0.005% to about 0.30% preferably from about 0.01% to about 0.10% by weight of the combined weight of the glycidyl ether of a dihydric phenol and the dihydric phenolic compound.
Suitable curing agents include, for example, guanidines such as dicyandiamide and tetramethyl guanidine and biguanides such as 2,6-xylene biguanide.
The curing agent is employed in quantities of from about 2 to about 8 preferably from about 3 to about 4 parts by weight per 100 parts or resin solids.
Suitable solvents include, for example, the oxygenated solvents such as acetone, methylethyl ketone, cyclohexanone, diacetone alcohol, mixtures thereof and the like, and the glycol ethers such as ethylene glycol, ethyl ether acetate; ethylene glycol, methyl ether; ethylene glycol, n-butyl ether; diethylene glycol, ethyl ether; diethylene glycol, n-butyl ether; propylene glycol, methyl ether; dipropylene glycol, methyl ether; mixtures thereof and the like and in admixture with aromatic solvents such as, for example, xylene, toluene, ethylbenzene and the like. Other suitable solvents include the halogenated solvents such as trichloroethylene, methylene chloride and the like and dimethyl formamide and the like.
The solvents are usually employed in quantities of from about 30 to about 80 preferably from about 40 to about 60 percent by weight based upon the total formulation.
Other components which can be included are accelerators such as, for example, imidazoles, benzyl dimethylamine, metaphenylene diamine, N,N,N',N'-tetramethyl-1-3-butanediamine and the like.
The accelerators are usually employed in quantities of from about 0.05 to about 1.0 preferably from about 0.1 to about 0.6 parts by weight per 100 parts resin solids.
Other components include wetting agents, colorants, fillers and the like.
Suitable substrates include, for example, fiberglass, polyester, and the like in woven or mat form.
An epoxy resin was prepared by reacting 73 g (.39 equiv.) of a diglycidyl ether of bisphenol A having an EEW of 187 with 27 g (0.10 equiv.) of tetrabromo bisphenol A in the presence of .075 g of tetramethylammonium hydroxide at a temperature of 170° C. for 120 minutes. The resultant epoxy resin had an EEW of 440.
An epoxy resin was prepared by reacting 66 g (0.353 equiv.) of a diglycidyl ether of bisphenol A having an EEW of 187 with 34 g (0.125 equiv.) of tetrabromo bisphenol A in the presence of 0.02 g of ethyl triphenyl phosphonium acetate acetic acid complex at a temperature of 160° C. for 120 minutes. The resultant resin had an EEW of 440.
The resin solutions also called prepreg varnish had the following compositions.
______________________________________                  COMPARATIVE        EXAMPLE 1 EXPERIMENT A______________________________________EPOXY RESIN A, grams          4848.0      --EPOXY RESIN B, grams          --          4343.0dicyandiamide, grams           140.0      130.0benzyl dimethylamine,           12.0        10.8 gramsacetone        1484.0      2097.0methylether of ethylene glycol, grams 1091.0      977.0Viscosity of solution at 25° C. 55 cps      52 cps______________________________________
Fiberglass cloth was impregnated by passing it through the prepreg varnish, followed by a pair of doctor bars set at 15 mils clearance to control resin pickup, and finally through an oven at 300° F. for a dwell time of approximately 4 minutes. The resulting B-staged impregnated cloth or prepreg had a gel time of 70 to 90 seconds at 175° C.
Laminates were then prepared from each of the above prepared preimpreganted fiberglass employing 5 plys of 12 in.×12 in. ×0.013 in. (3 cm×3 cm×0.33 mm) sheets of 7637 style glass with single plys of 7628 style glass on the outsides, all of which were I617 finish. The laminates were prepared by pressing at 500 psig (3500 kg/cm2) for 60 minutes at 175° C. The laminates were then tested. The results of the tests are given in Table I with the laminates prepared from Example 1 designated as laminate 1 while those prepared from Comparative Experiment A are designated as laminate A.
The pressure cooker-solder test was conducted by cutting 2 in×4 in coupons from prepared laminates, placing coupons edgewise on a rack in a pressure cooker and maintaining 15 pounds steam pressure for one hour, allowing coupons to equilibrate to ambient conditions for 30 minutes, and then immersing in 500° F. solder for 20 seconds. The laminates must be free blister after immersion in hot solder.
______________________________________             Laminate 1                     Laminate A______________________________________Glass Transition Temp. (Tg) ° C.               118° C.                         113° C.Flexural Strength, psi               80,638    76,185Flexural Modulus, psi               3.725 × 106                         3.3 × 106Tensile Strength, psi               56,648    60,577Tensile Modulus, psi               4.03 × 106                         4.04 × 106Copper Peel Strength (lbs/in)               9.6       10.4Volume Resistivity (L-cm)               1.0 × 1015                         1.0 × 1015Disipation Factor, Condition A,               .00580    .00900 105 cyclesDielectric Constant, Condition A,               3.9095    4.2025 105 cyclesPressure-Cooker-Solder TestCoupon No. 1        Pass      FailCoupon No. 2        Pass      FailCoupon No. 3        Pass      FailCoupon No. 4        Pass      FailCoupon No. 5        Pass      FailCoupon No. 6        Pass      FailCoupon No. 7        Pass      FailCoupon No. 8        Pass      Fail______________________________________
GB1434889A * Title not available
US4251594 * Sep 27, 1979 Feb 17, 1981 The Dow Chemical Company Process for preparing resin impregnated substrates for use in preparing electrical laminates
US4336302 * Feb 11, 1981 Jun 22, 1982 Siemens Aktiengesellschaft Insulating tape for fabricating an insulating sleeve for electric conductors impregnated with a thermo-setting epoxy resin/acid anhydride mixture
US6160077 * Nov 20, 1998 Dec 12, 2000 Siemens Aktiengesellschaft Halogen-free epoxy resin
US6743375 * Mar 8, 2002 Jun 1, 2004 Ardes Enterprises, Inc. Epoxy hardener of imidazole or trihydric compound with methylol groups, trimethylolpropane and tetramethylguanidine (adduct)
US7592067 Sep 22, 2003 Sep 22, 2009 Hexion Specialty Chemicals, Inc. Epoxy resin compositions, processes utilizing same and articles made therefrom
US20050065295 * Sep 22, 2003 Mar 24, 2005 Christiansen Walter H. Epoxy resin compositions, processes utilizing same and articles made therefrom
USRE32951 * Jun 30, 1983 Jun 13, 1989 The Dow Chemical Company Process for preparing epoxy resins having improved physical properties when cured using quaternary phosphonium catalysts
EP0027568A1 * Sep 25, 1980 Apr 29, 1981 The Dow Chemical Company Process for preparing resin impregnated substrates, resin impregnated substrate and electrical laminate therefrom
EP0556421A1 * Feb 18, 1992 Aug 25, 1993 The Dow Chemical Company Curable resin compositions
WO1982001877A1 * Dec 1, 1981 Jun 10, 1982 Dow Chemical Co A process for advancing epoxy resins in molecular weight and a process for preparing resin impregnated substrates
U.S. Classification 428/413, 427/99.4, 427/386, 174/258, 427/434.4, 428/417
International Classification C08G59/06, H05K1/03
Cooperative Classification H05K1/0326, Y10T428/31525, C08G59/066, Y10T428/31511
European Classification C08G59/06C

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4 bedroom terraced house for sale in Paragon Terrace, Cheltenham, Gloucestershire, GL53, GL53
www.rightmove.co.uk/property/55966206
Paragon Terrace, Cheltenham, Gloucestershire, GL53
A pretty Regency end of terrace town house sitting in a superb private position close to the centre of Cheltenham. The walled garden has a covered terrace and there is parking for 2/3 cars to the front of the property
No 1 Paragon Terrace is a pretty Regency town house set on a quiet private no through road.
Bordered by wrought iron railings with steps leading up to the front door. The lovely wide reception hall has a cantilevered staircase with pretty turned hand rail and leads to the main double reception room. The light and bright drawing/dining room has an abundance of period features including sash hung windows, period fire surrounds, detailed plaster work and ceiling roses and deep skirting's. The rooms are separated by parliament hinged doors.
Stairs down to the lower ground level lead to the kitchen/breakfast/ family room. This room has dual access with steps down from the front into a glazed porch with a door into the family/breakfast area and double French doors onto the terrace at the rear. There is stone flooring throughout the lower ground floor. The kitchen is fitted with a range of modern units with a central island and the breakfast has a feature fireplace. There is another access to the garden from this level with a large shower room and utility cupboard completing the accommodation on this floor.
Upstairs there is a family bathroom on the mezzanine level with steps up to a guest room with fitted wardrobes and lovely distant views to Cleeve Hill, a master bedroom with fitted wardrobes and a further small double.
To the rear there is a glazed pergola over the paved terrace creating the perfect place to enjoy the walled garden with deep planted beds and mature trees.
Situated on a private 'No through Road' in a central location enjoying privacy in the hub of Cheltenham and all it has to offer. Cheltenham has a comprehensive range facilities including an eclectic mixture of both shops and restaurants along with a wide range of excellent schools including Cheltenham Ladies' Collage, Dean Close and Cheltenham College.
To view this media, please visit the on-line version of this page at www.rightmove.co.uk/property-for-sale/property-55966206.html
Disclaimer - Property reference CHE180256. The information displayed about this property comprises a property advertisement. Rightmove.co.uk makes no warranty as to the accuracy or completeness of the advertisement or any linked or associated information, and Rightmove has no control over the content. This property advertisement does not constitute property particulars. The information is provided and maintained by Knight Frank, Cheltenham. Please contact the selling agent or developer directly to obtain any information which may be available under the terms of The Energy Performance of Buildings (Certificates and Inspections) (England and Wales) Regulations 2007 or the Home Report if in relation to a residential property in Scotland.
01 Mar 2016 5 Paragon Terrace, GL53 £815,000
23 Sep 2011 2 Paragon Terrace, GL53 £782,500
17 Dec 2010 6 Paragon Terrace, GL53 £650,000

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9783640843558: Eve with a Spade - AbeBooks - Iwona Eberle: 364084355X
ISBN 10: 364084355X ISBN 13: 9783640843558
Thesis (M.A.) from the year 2001 in the subject English Language and Literature Studies - Literature, grade: 1, University of Zurich (Englisches Seminar), language: English, abstract: Women have been closely associated with gardens: for a perceived similarity to their 'nature', for the garden's connection to the domestic sphere, and, not least, for their connection by the 'hortus conclusus' motif, referring back to the Bible. This connection became even stronger in 19th century England. In the wake of the general gardening rage it became possible for women to pursue gardening as a career. Women began to emerge as competent authors of gardening books, and in imaginative literature, too, women in particular showed no restraint in declaring their passion for the garden. The most important among them was Elizabeth von Arnim (1866-1941), an Australian-born British novelist. In her bestselling novels "Elizabeth and Her German Garden" (1898), as well as in the two sequels "The Solitary Summer" (1899) and "The Pious Pilgrimage" (1901), the autobiographical heroine Elizabeth enjoys ecstatic, creative freedom in her Pomeranian garden. This thesis explores the relationship between gardens and their representation in literature, the relationship between women and gardens in the 19th century, and the function of the garden for the main character and narrator in works by writer Elizabeth von Arnim. In von Arnim's works, the garden is a protected space of liberty. It enables a return to childhood, it restores the female speaker to her original self, is a space for creativity, offers freedom from familial restraints and society's roles, and provides independence and room for ecstatic feelings. It acts as an ally in a patriarchal and materialistic society, and it is, in general, the central object and issue against and through which the female speaker defines herself. Von Arnim draws on a multitude of literary models and traditions related to gardens, and to women in gardens,
Book Description Grin Publishing, 2011. PAP. Book Condition: New. New Book.Shipped from US within 10 to 14 business days.THIS BOOK IS PRINTED ON DEMAND. Established seller since 2000. Bookseller Inventory # IP-9783640843558
Book Description Grin Publishing, 2011. PAP. Book Condition: New. New Book. Delivered from our US warehouse in 10 to 14 business days. THIS BOOK IS PRINTED ON DEMAND.Established seller since 2000. Bookseller Inventory # IP-9783640843558
Book Description GRIN Publishing, 2017. Paperback. Book Condition: New. Never used! This item is printed on demand. Bookseller Inventory # 364084355X
5. Eve with a Spade (Paperback or Softback)
Book Description Grin Publishing 9/29/2013, 2013. Paperback or Softback. Book Condition: New. Eve with a Spade. Book. Bookseller Inventory # BBS-9783640843558
6. Eve with a Spade
Book Description GRIN Publishing, 2011. Book Condition: New. Bookseller Inventory # I-9783640843558
7. Eve with a Spade
Book Description GRIN Publishing, 2011. Book Condition: New. This item is printed on demand for shipment within 3 working days. Bookseller Inventory # LP9783640843558
8. Eve with a Spade
9. Eve with a Spade
Book Description GRIN Publishing, 2016. Paperback. Book Condition: New. PRINT ON DEMAND Book; New; Publication Year 2016; Not Signed; Fast Shipping from the UK. No. book. Bookseller Inventory # ria9783640843558_lsuk
10. Eve with a Spade
Book Description GRIN Publishing. PAPERBACK. Book Condition: New. 364084355X Special order direct from the distributor. Bookseller Inventory # ING9783640843558

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Mango Promo Code - Mango Promo Code | Groupon
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Scott Electric in Corpus Christi, TX with Reviews - YP.com
Corpus Christi, TX Scott Electric
4. Scott's Electronics
5. Mathieu Electric Commercial, LLC
6. Dave's Electrical Services, Inc.
7. Martin Electric Co Inc.
8. Budd Electric
SAMBA DrCorpus Christi, TX 78414
10. CW Campbell Electric Inc.
11. Rabalais I & E Constructors
12. Malek Inc
15. Advantage Electric Inc
16. Ledbetter Electric
17. Rabalais Electric
(361) 561-8110
18. Pike Electric
19. Aguilar R Electric Inc
8279 Leopard StCorpus Christi, TX 78409
(361) 241-1989
20. Computer Cable Service Inc
2801 Thunder Bay CtsCorpus Christi, TX 78414
(361) 991-4757
21. Rosendin Electric
22. T L Electric
4717 Westway DrCorpus Christi, TX 78408
(361) 814-7748
23. Custom Electrical Service - CLOSED
1838 Talisman StCorpus Christi, TX 78416
24. Adrian Enterprises, Inc.
25. C & I Electrical Contractors
2801 S Port AveCorpus Christi, TX 78405
(361) 885-0315
26. Palacios Electric Co
4137 Sierra CirCorpus Christi, TX 78410
(361) 242-2214
27. Ays Live Sound Inc
4437 Green Grove DrCorpus Christi, TX 78415
(361) 855-4675
28. AEP Texas Central Company
5502 Corporate DrCorpus Christi, TX 78405
(361) 299-6348
29. T & D Solutions
30. Lamp Lighter Electrical Contractor
(361) 985-7485
Related Articlesfor Scott Electricmore related articles »
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value: This website is a United States-based web site operated by YP Holdings that provides listings for local businesses. In 2013 it was re-branded as YP.com or simply "YP".


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User ID joemama1931 (Feedback score 48979)
Honda rear wheel axle TRX 250X / TRX 300EX Fourtrax / Sportrax 1987 1988 - 2009 (Fits: 1987 Honda)
Honda TRX Rear Axle bearing carrier 250X / 300X / 300EX / 350X 1987-2009 (Fits: 1987 Honda)
Fuel Petcock Switch/Valve FIT Honda TRX200SX FourTrax TRX250 TRX250X TRX300 USA (Fits: 1987 Honda)
Carburetor For Honda ATC250R TRX250 TRX250X TRX250R Suzuki LT250R LT500R (Fits: 1987 Honda)
1987-1990 Suzuki Quadracer 500 LT500R. 1985-1990 Suzuki Quadracer 250 LT250R. 1981-1986 Honda ATC250R. 1985-1992 Honda FourTrax 250. 7.0 Slide. 55 Pilot Jet. 170 Main Jet.
TIE ROD END KIT for HONDA TRX250X 250 X FOURTRAX 1987 1988 1991 1992
TRX250X FOURTRAX 1987, 1988, 1991, 1992. TIE ROD END KIT. FITS: HONDA.
Honda TRX250X 1987-1992 Front Wheel Bearings & Seals TRX 250X (Fits: 1987 Honda)
You are looking at a Front Wheel bearing and seal kit for years 1987-1992 Honda TRX250X. This will do both front wheels.
Fuel Petcock For Honda TRX200SX TRX250 TRX250X ATC250ES ATC250SX ATC350X TRX30 (Fits: 1987 Honda)
Carburetor Carb Rebuild Kit Repair For Honda Fourtrax TRX250X 87 88 91 92 TRX250 (Fits: 1987 Honda)
1987 1988, 1991 1992 Honda Fourtrax TRX250X.
FRONT REAR BRAKE PADS FITS HONDA TRX250X TRX 250 X FOURTRAX 1987 1988 1989-1992 (Fits: 1987 Honda)
TRX250X FOURTRAX 1987-1992. FRONT REAR BRAKE PADS. FITS: HONDA.
HONDA TRX250X Seat Cover 1987 - 1992 in 2-tone or 25 Colors (HONDA SIDES)
Honda TRX250X. 1987 - 1992 Models. DEMO PICS SHOWN IN VARIOUS OPTIONS. IF NO PREFERENCES ARE MADE YOU WILL RECEIVE Asolid black SEAT COVER AS OUR DEFAULT OPTION WITH HONDA ON SIDES IN WHITE. If no pre...
In great shape. Has paint wear. Ready to mount and ride.
1987-92 Honda TRX250X Wiseco Cam Chain (Fits: 1987 Honda)
Honda TRX250X 1987-1988 & 1991-1992 CARBURETOR Carb Rebuild Kit Repair TRX 250X (Fits: 1987 Honda)
New 1987-1992 Honda TRX250X Ignition Key Switch KS105R (Fits: 1987 Honda)
1987 Honda TRX250x Stator
1987 Honda TRX250x Cylinder Head
Cylinder Head removed from a 1987 Honda TRX250x. In working condition. All parts are USED unless otherwise noted. What you see in the pictures is what you will get so inspect them carefully. Each part...
87-92 Honda TRX250X Moose Racing Stator M21-614H (Fits: 1987 Honda)
Fit Models: TRX250X. Make: Honda.
This is the carburetor. Removed from a 1987 Honda TRX 250x. Arctic Cat ATK Bombardier Can Am Car & Truck Parts Harley Davidson Honda Husaberg Kawasaki KTM MX/ATV Parts & Accessories Polaris Rupp Skido...
1987 Honda TRX250x Dura Blue Axle
Dura Blue Axle - Missing Spacers - removed from a 1987 Honda TRX250x. In working condition. All parts are USED unless otherwise noted. What you see in the pictures is what you will get so inspect them...
Wiring Harness removed from a 1987 Honda TRX250x. In working condition. All parts are USED unless otherwise noted. What you see in the pictures is what you will get so inspect them carefully. Each par...
IGNITION COIL + CDI Fit Honda TRX250X FOURTRAX 1987 1988 1989 1990 1991 1992 ATV (Fits: 1987 Honda)
1987 Honda 250X Head
Head has no cracks, or dents. Valves and seats are good. Cam is in good condition. Teeth are good with none missing or chipped. Valve covers are not bent or cracked. Has good chain tensioner.
1987 Honda TRX 250 X 2WD Rear Axle/ Hubs
The axle is not bent, broken, or cracked. It is very straight. Splines do not show any wear. The hubs are not cracked, bent, or broken. The bolts are not broken, cracked, or stripped. All parts are in...
1987 87 HONDA TRX 250X SEAT
*EP* 1987 Honda TRX250X Fourtrax 2wd - Head
Head is not bent, broken, chipped, dented, or cracked. Good condition.
Hond ATC350X (1985-1986). Honda ATC250SX (1985-1987). Honda Big Red 250 (1985-1987). Honda FourTrax 200 (1986-1988). Honda FourTrax 250 (1985-1992). Honda FourTrax 300 (1988-2000). Honda Sportrax 250 ...
About 1987 Honda 250X


text:
Geography Alive 8 for the Ac & Ebk + History Alive 8 for the Ac & Ebk + Jacaranda Atlas for the Ac 8E (Includes Myworld Atlas Ac) by Judy Mraz: 9780730308386 1st. - AbeBooks.com
Home Judy Mraz Geography Alive 8 for the Ac & Ebk + History Alive 8 for the Ac ...
Geography Alive 8 for the Ac & Ebk + History Alive 8 for the Ac & Ebk + Jacaranda Atlas for the Ac 8E (Includes Myworld Atlas Ac)
ISBN 10: 0730308383 / ISBN 13: 9780730308386
Jacaranda's latest resources for Australian Curriculum Geography and History offer new ways to engage students. High impact artwork, a wealth of resources and structured activities build on the po.Shipping may be from multiple locations in the US or from the UK, depending on stock availability. 2.600. Bookseller Inventory #
Title: Geography Alive 8 for the Ac & Ebk + History...


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Buttermere, Cumbria - Wikipedia
For the lake of the same name, see Buttermere.
Buttermere village (centre), with Grasmoor (above), Buttermere lake (below), and Crummock Water (left).
Buttermere shown within Cumbria
121 (2011)
NY174170
54°32′30″N 3°16′32″W / 54.541543°N 3.275625°W / 54.541543; -3.275625Coordinates: 54°32′30″N 3°16′32″W / 54.541543°N 3.275625°W / 54.541543; -3.275625
Buttermere is a village and civil parish in the county of Cumbria, England.
2 Civil parish
The village of Buttermere lies between the Lake District lakes of Buttermere and Crummock Water, and is overlooked by the summits of Grasmoor to the north and High Stile to the south. The nearest towns are Keswick and Cockermouth, both of which are approximately 10 miles (16 km) away.[1]
In the village, The Bridge Hotel, stands on a site tracing back to the 11th century, where an armoury and a bakery stood, in connection with the Water-Mill Earl Boether built higher up the stream. For seven centuries the mill worked continuously, the buildings being many times renewed. Circa 1734, the buildings were sold to the church, the curate being the Reverend Robert Walker. He obtained a beer licence and originated the 'Bridge Inn'. In 1837, Jonathan Thomas Sleap purchased the property, rebuilding the inn using stone obtained from the old water will. He changed the name to 'Victoria' upon the visit by Her Majesty in 1850. In 1861, Mrs H Cooper inherited the property incorporating the bay windows, but it was the author Nicholas Size, who in 1920 extended and improved the building. Upon his death the new owner changed the name to 'The Bridge'. Peter and Janet McGuire who bought the hotel 1978, have owned the premises to the present day.
Buttermere is situated on the B5289 road that runs beside Crummock Water and along the valley of the River Cocker north to Cockermouth. In the other direction, the B5289 runs via the steep Honister Pass, to Borrowdale and Keswick. A more direct, but more minor, road crosses the nearby Newlands Pass into the Newlands Valley and hence to Keswick.
The civil parish of Buttermere covers a considerable area around the village, including both Buttermere and Crummock Water lakes, the summit of Grasmoor, the north side of High Stile and the western side of Honister Pass. The smaller settlements of Brackenthwaite, to the north of Crummock Water, and Gatesgarth, at the foot of the Honister Pass, are included. The parish lies entirely within the Lake District National Park. At the time of the 2001 census the parish had a population of 127 living in 49 households,[2][3] falling slightly at the 2011 Census to a population of 121 in 45 households.[4]
For local government purposes the civil parish forms part of the district of Allerdale within the county of Cumbria. Historically part of Cumberland, it is within the Workington constituency of the United Kingdom Parliament, and the North West England constituency of the European Parliament.[2]
Mary Robinson (1778–1837) — known as "The Maid of Buttermere" and the subject of Melvyn Bragg's novel of that name.
Listed buildings in Buttermere, Cumbria
^ "Buttermere, Cumbria, The Lake District". The Cumbria Directory. Retrieved 2010-01-13. ^ a b "Election Maps". Ordnance Survey. Retrieved 2010-01-02. ^ "Census 2001 : Parish Headcounts : Allerdale". Office for National Statistics. Retrieved 2009-11-22. ^ "Parish population 2011". Retrieved 17 June 2015. External links[edit]
Media related to Buttermere, Cumbria at Wikimedia Commons
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