US4512898A
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Packing materials for chromatographic use and a method for analysis of an enantiomer mixture using the same
Assignee: Sumitomo Chemical Co Ltd
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Filing: 1983-09-30
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Granted: 1985-04-23
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Expires: 2003-09-30
Abstract
Abstract A packing material for chromatographic use comprising an inorganic carrier having hydroxyl groups at the surface thereof having grafted thereon an organosilane derivative selected from the group consisting of a urea derivative obtained by reacting an optically active isocyanate with an aminoalkylsilane, an N-carbomoyl amino acid derivative obtained by reacting an optically active amino acid carbamoylated by isocyanate with an aminoalkylsilane and an O-carbamoyl hydroxy acid derivative obtained by reacting an optically active hydroxy acid carbamoylated by isocyanate with an aminoalkylsilane is disclosed. This packing material is useful as a packing material for liquid chromatography analysis which comprises separating and analyzing an enantiomer mixture of a compound having an -OH group, a -CONH- group, <IMAGE> a -COO- group, an -NHCOO- group, an -NHCONH- group or <IMAGE> bonded to an asymmetric carbon atom thereof.
Inventors
- 👤 Naobumi Oi
- 👤 Hajimu Kitahara
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 22:51
CPC Classifications
B; B01; B01D; B01D15/00; B01D15/08; B01D15/26; B01D15/38; B01D15/3833; B01J; B01J20/00; B01J20/02; B01J20/10; B01J20/103; B01J20/28; B01J20/28002; B01J20/28004; B01J20/28054; B01J20/28057; B01J20/28078; B01J20/28083; B01J20/281; B01J20/29; B01J20/30; B01J20/3092; B01J20/32; B01J20/3202; B01J20/3204; B01J20/3231; B01J20/3242; B01J20/3244; B01J20/3246; B01J20/3257; B01J20/3259; B01J20/3261; B01J2220/00; B01J2220/50; B01J2220/54; B01J2220/58
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
70 words
A packing material for chromatographic use which comprises an inorganic carrier having hydroxyl groups at the surface thereof to which an organosilane derivative selected from the group consisting of an N-carbamoyl amino acid derivative obtained by reacting an optically active amino acid carbamoylated by isocyanate with an aminoalkylsilane and an O-carbamoyl hydroxy acid derivative obtained by reacting an optically active hydroxy acid carbamoylated by isocyanate with an aminoalkylsilane is grafted.
Claim 2
Dependent Claim
70 words
A packing material for chromatographic use which comprises an inorganic carrier having hydroxyl groups at the surface thereof to which an organosilane derivative selected from the group consisting of an N-carbamoyl amino acid derivative obtained by reacting an optically active amino acid carbamoylated by isocyanate with an aminoalkylsilane and an O-carbamoyl hydroxy acid derivative obtained by reacting an optically active hydroxy acid carbamoylated by isocyanate with an aminoalkylsilane is grafted.
Claim 3
Dependent Claim
150 words
A packing material for chromatographic use as claimed in claim 1, wherein said organosilane derivative is an organosilane represented by the general formula: ##STR16## wherein R 1 , R 2 and R 3 each, which may be the same or different, is an alkyl group, an alkoxy group, a hydroxyl group or a halogen atom, with the proviso that at least one of R 1 , R 2 and R 3 is an alkoxyl group or a halogen atom; R 4 is an alkyl group, an aryl group or an aralkyl group; R 5 is an alkyl group, an aryl group or an aralkyl group which may be substituted with an aryl group including those groups which are optically active substituents; X is an --NHCO-- group or an --N.sup.⊕ H 3 .O.sup.⊖ CO-- group; Y is an --NH-- group or an oxygen atom; and l is 2, 3 or 4.
Claim 4
Dependent Claim
25 words
A packing material for chromatographic use as claimed in claim 1, wherein said inorganic carrier having hydroxyl groups at the surface thereof is silica gel.
Claim 5
Dependent Claim
27 words
A packing material for chromatographic use as claimed in claim 2, wherein the aminoalkylsilane residue in general formula (I) is an ω-aminopropyltriethoxysilane residue or an ω-aminopropyltrichlorosilane residue.
Claim 6
Dependent Claim
64 words
A packing material for chromatographic use as claimed in the claim 2, wherein in general formula R 4 is an isopropyl group or a phenyl group; and R 5 is an n-propyl group, an isopropyl group, a tert-butyl group, a phenyl group, a 3,5-dinitrophenyl group, an α-naphthyl group, an optically active 1-(α-naphthyl)ethyl group, an optically active 1-phenylethyl group, or an optically active 1phenyl-2-2-(4-tolyl)ethyl group.
Claim 7
Dependent Claim
39 words
A packing material for chromatographic use as claimed in the claim 2, wherein in general formula; R 4 is an isopropyl group or a phenyl group; and R 5 is a tert-butyl group or an optically active 1-(α-naphthyl)ethyl group.
Claim 8
Independent Claim
114 words
A method for liquid chromatography analysis which comprises separating and analyzing an enantiomer mixture of a compound having an --OH group, a --CONH-- group, ##STR17## a --COO-- group, an --NHCOO-- group, an --NHCONH-- group or an ##STR18## bonded to an asymmetric carbon atom thereof by using a packing material for chromatographic use obtained by grafting on an inorganic carrier having hydroxyl groups at the surface thereof an organosilane derivative selected from the group consisting of an N-carbamoyl amino acid derivative obtained by reacting an optically active amino acid carbamoylated by isocyanate with an aminoalkylsilane and an O-carbamoyl hydroxy acid derivative obtained by reacting an optically active hydroxy acid carbamoylated by isocyanate with an aminoalkylsilane.
Claim 9
Independent Claim
114 words
A method for liquid chromatography analysis which comprises separating and analyzing an enantiomer mixture of a compound having an --OH group, a --CONH-- group, ##STR17## a --COO-- group, an --NHCOO-- group, an --NHCONH-- group or an ##STR18## bonded to an asymmetric carbon atom thereof by using a packing material for chromatographic use obtained by grafting on an inorganic carrier having hydroxyl groups at the surface thereof an organosilane derivative selected from the group consisting of an N-carbamoyl amino acid derivative obtained by reacting an optically active amino acid carbamoylated by isocyanate with an aminoalkylsilane and an O-carbamoyl hydroxy acid derivative obtained by reacting an optically active hydroxy acid carbamoylated by isocyanate with an aminoalkylsilane.
Claim 10
Dependent Claim
147 words
A method for analysis as claimed in claim 7, wherein said organosilane derivative is an organosilane represented by the general formula: ##STR19## wherein R 1 , R 2 and R 3 each, which may be the same or different, is an alkyl group, an alkoxyl group, a hydroxyl group or a halogen atom, with the proviso that at least one of R 1 , R 2 and R 3 is an alkoxyl group or a halogen atom; R 4 is an alkyl group, an aryl group or an aralkyl group; R 5 is an alkyl group, an aryl group or an aralkyl group which may be substituted with an aryl group including those groups being optically active substituents; X is an --NHCO-- group or an --N.sup.⊕ H 3 .O.sup.⊖ CO-- group; Y is an --NH-- group or an oxygen atom; and l is 2, 3 or 4.
Claim 11
Dependent Claim
23 words
A method for analysis as claimed in claim 7, wherein said inorganic carrier having hydroxyl groups at the surface thereof is silica gel.
Claim 12
Dependent Claim
25 words
A method for analysis as claimed in claim 8, wherein the aminoalkylsilane residue in the general formula is an ω-aminopropyltriethoxysilane residue or an ω-aminopropyltrichlorosilane residue.
Claim 13
Dependent Claim
62 words
A method for analysis as claimed in claim 8, wherein in the general formula; R 4 is an isopropyl group or a phenyl group; and R 5 is an n-propyl group, an isopropyl group, a tert-butyl group, a phenyl group, a 3,5-dinitrophenyl group, an α-naphthyl group, an optically active 1-(α-naphthyl)ethyl group, an optically active 1-phenylethyl group or an optically active 1-phenyl-2-(4-tolyl)ethyl group.
Claim 14
Dependent Claim
37 words
A method for analysis as claimed in claim 8, wherein in the general formula R 4 is an isopropyl group or a phenyl group; and R 5 is a tert-butyl group or an optically active 1-(α-naphthyl)ethyl group.
References Cited (Backward Citations)
US3984349A
Cited
US4190425A
Cited
US3960521A
Cited
US4322310A
Cited
US4324681A
Cited
US4368275A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-04-22 | 1988-10-22 | 1989-04-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-04-22 | 1992-10-22 | 1993-04-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-04-22 | 1996-10-22 | 1997-04-23 | $7700.00 | Window Closed / Lapsed |