US5162155A — Silane coated inorganic materials for chromatogra…

Claim 1

Independent Claim 331 words

An inorganic substrate having a coating comprised of a silane derivative of the formula I ##STR9## wherein X is H or CH 3 , R 1 , R 2 and R 3 are in each case, independently of one another, halogen; C 1 -C 12 -alkyl; C 1 -C 12 -alkyl wherein one or two non-adjacent CH 2 groups are replaced by --O--, --CO--, --CH═CH--, --OCO--, --COO-- or a combination thereof; phenyl, phenylalkyl, phenoxy, phenylalkoxy or a derivative thereof wherein the phenyl group in each case can also be substituted by halogen, alkyl, alkoxy or a combination thereof, wherein the alkyl chain in each case has up to 12 C atoms; or cycloalkyl, alkylcycloalkyl or a derivative thereof which is substituted by alkyl, wherein the cyclic ring has 3-10 C atoms and the alkyl chain in each case has up to 12 C atoms; and R 4 and R 5 a) are in each case, independently of one another, hydrogen; alkyl which can be substituted by cycloalkyl, cyano, amino, or hydroxyl; naphthyl, naphthylalkyl, phenyl, phenylalkyl or a derivative thereof which is substituted by alkyl, cycloalkyl, halogen, cyano, amino or hydroxyl, wherein the alkyl group in each case has up to 12 C atoms and includes alkyl substituents having one or two non-adjacent CH 2 groups replaced by --O--, --CO--, --CH═CH--, --OCO--, --COO--, ##STR10## wherein two hetero atoms are not linked to one another; or b) together form an alkylene bridge of up to 7 C atoms; or c) are a cycloalkyl or alkylcycloalkyl radical having 3-10 C atoms in the ring and from 1-12 carbon atoms in the alkyl group; or d) are mono- or oligosaccharides; or e) are such that the formula --NR 4 R 5 defines an amino acid derivative which is bonded via the nitrogen atom and has up to 15 C atoms in the main chain; with the proviso that at least one of R 1 , R 2 or R 3 is a reactive leaving group.

Claim 2

Dependent Claim 331 words

An inorganic substrate having a coating comprised of a silane derivative of the formula I ##STR9## wherein X is H or CH 3 , R 1 , R 2 and R 3 are in each case, independently of one another, halogen; C 1 -C 12 -alkyl; C 1 -C 12 -alkyl wherein one or two non-adjacent CH 2 groups are replaced by --O--, --CO--, --CH═CH--, --OCO--, --COO-- or a combination thereof; phenyl, phenylalkyl, phenoxy, phenylalkoxy or a derivative thereof wherein the phenyl group in each case can also be substituted by halogen, alkyl, alkoxy or a combination thereof, wherein the alkyl chain in each case has up to 12 C atoms; or cycloalkyl, alkylcycloalkyl or a derivative thereof which is substituted by alkyl, wherein the cyclic ring has 3-10 C atoms and the alkyl chain in each case has up to 12 C atoms; and R 4 and R 5 a) are in each case, independently of one another, hydrogen; alkyl which can be substituted by cycloalkyl, cyano, amino, or hydroxyl; naphthyl, naphthylalkyl, phenyl, phenylalkyl or a derivative thereof which is substituted by alkyl, cycloalkyl, halogen, cyano, amino or hydroxyl, wherein the alkyl group in each case has up to 12 C atoms and includes alkyl substituents having one or two non-adjacent CH 2 groups replaced by --O--, --CO--, --CH═CH--, --OCO--, --COO--, ##STR10## wherein two hetero atoms are not linked to one another; or b) together form an alkylene bridge of up to 7 C atoms; or c) are a cycloalkyl or alkylcycloalkyl radical having 3-10 C atoms in the ring and from 1-12 carbon atoms in the alkyl group; or d) are mono- or oligosaccharides; or e) are such that the formula --NR 4 R 5 defines an amino acid derivative which is bonded via the nitrogen atom and has up to 15 C atoms in the main chain; with the proviso that at least one of R 1 , R 2 or R 3 is a reactive leaving group.

Claim 3

Dependent Claim 88 words

An inorganic substrate as in claim 1, wherein R 1 , R 2 , R 3 of Formula I are in each case, independently of one another, halogen; C 1 -C 7 -alkyl; C 1 -C 7 -alkyl wherein one CH 2 group is replaced with --O--; phenyl or a derivative thereof wherein the phenyl group is substituted by halogen, C 1 -C 12 -alkyl, C 1 -C 12 -alkoxy or a combination thereof; or cycloalkyl, alkylcycloalkyl or a derivative thereof substituted by C 1 -C 12 -alkyl.

Claim 4

Dependent Claim 216 words

An inorganic substrate as in claim 1, wherein R 1 , R 2 and R 3 of Formula I are in each case, independently of one another: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, isopropyl, isobutyl, sec.- or tert.-butyl, 3-methylbutyl, 1,1-, 1,2- or 2,2-dimethylpropyl, 1-ethylpropyl; or methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, isopropoxy, isobutoxy, sec.- or tert.-butoxy, 3-methyl-butoxy, 1-ethylpropoxy, methoxymethyl, ethoxymethyl, 2-methoxyethyl, 2-, 3- or 4-oxapentyl, 2-, 3-, 4- or 5-oxahexyl, 2-, 3-, 4-, 5- or 6-oxaheptyl, 2-oxa-3-methylbutyl, 3-oxa-4-methylbutyl, 2-methyl-3-oxapentyl, 2-methyl-3-oxahexyl, octyl, nonyl, decyl, undecyl, dodecyl, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, 2-octyl or 2-octyloxy; or phenyl, phenoxy, benzyl, 1- or 2-phenylethyl, o-, m- or p-methylbenzyl, 1- or 2-o-, -m- or -p-tolylethyl, o-, m- or p-ethylbenzyl, 1- or 2-o-, -m- or -p-ethylphenylethyl, o-, m- or p-methoxyphenyl, 1- or 2-o-, -m- or -p-methoxyphenylethyl, o-, m- or p-fluorophenyl, o-, m- or p-fluorobenzyl, o-, m- or p-chlorophenyl, o-, m- or p-chlorobenzyl, 1- or 2-o-, -m- or -p-chlorophenylethyl, o-, m- or p-bromophenyl, o-, m- or p-iodophenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-dimethoxyphenyl or 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-dimethoxybenzyl; or cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl or cyclodecyl, 4-ethylcyclohexyl, 4-propylcyclohexyl, 4-butylcyclohexyl, 4-isopropylcyclohexyl, 3-ethylcyclopropyl 5-ethylcyclooctyl, cyclohexylmethyl, 1- or 2-cyclohexylethyl, 2-, 3- or 4-methylcyclohexylmethyl, 2-, 3- or 4-ethylcyclohexylmethyl, 2-, 3-, or 4-tert.-butylcyclohexylmethyl or 1- or 2-(2-, 3- or 4-ethylcyclohexyl)-ethyl.

Claim 5

Dependent Claim 43 words

An inorganic substrate as in claim 3, wherein R 4 and R 5 of Formula I are, in each case, independently of one another, selected from the same group of radicals as R 1 , R 2 and R 3 and additionally hydrogen.

Claim 6

Dependent Claim 29 words

An inorganic substrate as in claim 1, wherein R 4 and R 5 of Formula I together form an alkylene group which is propylene, butylene, pentylene, hexylene, or heptylene.

Claim 7

Dependent Claim 26 words

An inorganic substrate as in claim 1, wherein the reactive leaving group of R 1 , R 2 or R 3 of Formula I is ##STR11##

Claim 8

Dependent Claim 40 words

An inorganic substrate as in claim 1, wherein R 1 , R 2 and R 3 of Formula I provide the following combinations of substituents on the silicon atom: dimethylchloro-, triethoxy-, trichloro-, phenyldichloro-, methyldichloro-, diethoxymethyl-, diethylchloro-, trimethoxy-, ethyldichloro- and dimethoxymethyl-.

Claim 9

Dependent Claim 30 words

An inorganic substrate as in claim 1, wherein R 4 and R 5 of Formula I are radicals of hexoses, pentoses, fructoses, glycosides, pyranoses, furanoses, pyranosides, furanosides, disaccharides or trisaccharides.

Claim 10

Dependent Claim 26 words

An inorganic substrate as in claim 1, wherein R 4 and R 5 of Formula I are glucosyl, arabinosyl, ribosyl, galatosyl, fructosyl, lactose or sucrose radicals.

Claim 11

Dependent Claim 44 words

An inorganic substrate as in claim 1, wherein R 4 and R 5 of Formula I are such that the formula --NR 4 R 5 defines an amino acid derivative which is a free acid, ester, amide or substituted amide or an amino acid.

Claim 12

Dependent Claim 77 words

An inorganic substrate as in claim 1, wherein R 4 and R 5 of Formula I are such that the formula --NR 4 R 5 defines a free acid, C 1-7 -alkyl ester, phenyl ester, amide, C 1-7 -alkyl or phenyl substituted amide of an amino acid which is glycine, β-alanine, alanine, ε-aminocaproic acid, phenylalanine, α-aminoisobutyric acid, 4-aminobenzoic acid, valine, leucine, isoleucine, serine, threonine, aspartic acid, asparagine, glutamic acid, glutamine, lysine, arginine, histidine, tyrosine, tryptophan or ornithine.

Claim 13

Dependent Claim 33 words

An inorganic substrate as in claim 1, wherein R 4 and R 5 of Formula I form one of the following radicals on the silicon atoms, where x=hydrogen or CH 3 , ##STR12##

Claim 14

Dependent Claim 14 words

A chromatographic carrier having a coating comprised of a silane derivative of claim 1.

Claim 15

Dependent Claim 39 words

A chromatographic carrier as in claim 13 comprised of silica gel, TiO 2 or Al 2 O 3 and R 4 and R 5 of formula I are such that --NR 4 R 5 defines an amino acid derivative.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1995-11-10	1996-05-11	1996-11-10	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1999-11-10	2000-05-11	2000-11-10	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	2003-11-10	2004-05-11	2004-11-10	$7700.00	Window Closed / Lapsed

Silane coated inorganic materials for chromatography

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