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US4604207A
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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: 1983-05-18
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Granted: 1986-08-05
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Expires: 2003-05-18
Abstract
Abstract PCT No. PCT/JP83/00145 Sec. 371 Date Jan. 18, 1984 Sec. 102(e) Date Jan. 18, 1984 PCT Filed May 18, 1983 PCT Pub. No. WO83/04103 PCT Pub. Date Nov. 24, 1983.A packing material for chromatographic use which comprises an inorganic carrier having hydroxyl groups at the surface thereof having grafted thereon an alpha -arylalkylamine derivative which is formed by bonding an optically active alpha -arylalkylamine and an aminoalkylsilane through a dibasic carboxylic acid, and a method for liquid chromatographic analysis of an enantiomer mixture using this packing material as a stationary phase. The packing material of the present invention can be easily produced by the usual chemical reaction, is chemically stable, and exhibits excellent effects in the separation of an enantiomer mixture of a compound having an -NH- group, -CONH- group, or an -OCO- group bonded to an asymmetric carbon atom thereof.
Inventors
- 👤 Naobumi Oi
- 👤 Tadashi Doi
- 👤 Masayuki Nagase
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 20:28
CPC Classifications
B; B01; B01J; B01J20/00; B01J20/281; B01J20/286; B01J20/289; B01J20/29; B01J20/30; B01J20/32; B01J20/3202; B01J20/3204; B01J20/3214; B01J20/3217; B01J20/3219; B01J20/3221; 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: 12
Claim 1
Independent Claim
151 words
A packing material for chromatographic use which comprises an inorganic carrier having hydroxyl groups at the surface thereof having grafted thereon an α-arylalkylamine derivative which is formed by bonding an optically active α-arylalkylamine and an aminoalkylsilane through a dibasic carboxylic acid, wherein the grafted α-arylalkylamine derivative is an organosilane represented by general formula (I): ##STR9## 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 proviso that at least one thereof is an alkoxyl group or a halogen atom; R 4 is an alkyl group; Ar is a naphthyl group, which may be substituted; X is --NHCO-- or --N.sup.⊕ H 3 .O.sup.⊖ CO--; Y is a lower alkylene group or a phenylene group; n is an integer of from 2 to 4; and * indicates an asymmetric carbon atom.
Claim 2
Dependent Claim
151 words
A packing material for chromatographic use which comprises an inorganic carrier having hydroxyl groups at the surface thereof having grafted thereon an α-arylalkylamine derivative which is formed by bonding an optically active α-arylalkylamine and an aminoalkylsilane through a dibasic carboxylic acid, wherein the grafted α-arylalkylamine derivative is an organosilane represented by general formula (I): ##STR9## 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 proviso that at least one thereof is an alkoxyl group or a halogen atom; R 4 is an alkyl group; Ar is a naphthyl group, which may be substituted; X is --NHCO-- or --N.sup.⊕ H 3 .O.sup.⊖ CO--; Y is a lower alkylene group or a phenylene group; n is an integer of from 2 to 4; and * indicates an asymmetric carbon atom.
Claim 3
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 4
Dependent Claim
25 words
A packing material for chromatographic use as claimed in claim 2, wherein the α-arylalkylamine residue in general formula (I) is an optically active 1-(α-naphthyl)ethylamine residue.
Claim 5
Dependent Claim
29 words
A packing material for chromatographic use as claimed in claim 2 or 3, wherein the aminoalkylsilane residue in general formula (I) is an ω-aminopropyltriethoxysilane residue or an ω-aminopropyltrichlorosilane residue.
Claim 6
Dependent Claim
31 words
A packing material for chromatographic use as claimed in claim 4, wherein the dibasic carboxylic acid residue in general formula (I) is a succinic acid residue or a terephthalic acid residue.
Claim 7
Independent Claim
187 words
A method for liquid chromatographic analysis which comprises separating and analyzing an enantiomer mixture of a compound having an --NH-- group, a --CONH-- group, or an --OCO-- group bonded to an asymmetric carbon atom thereof by using a packing material for chromatographic use comprising an inorganic carrier having hydroxyl groups at the surface thereof having grafted thereon an α-arylalkylamine derivative which is formed by bonding an optically active α-arylkalkylamine and an aminoalkylsilane through a dibasic carboxylic acid, wherein the grafted α-arylalkylamine derivative is an organosilane represented by general formula (I): ##STR10## 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 proviso that at least one thereof is an alkoxyl group or a halogen atom; R 4 is an alkyl group; Ar is a naphthyl group, which may be substituted; X is --NHCO-- or --N.sup.⊕ H 3 .O.sup.⊖ CO--; Y is a lower alkylene group or a phenylene group; n is an integer of from 2 to 4; and * indicates an asymmetric carbon atom.
Claim 8
Independent Claim
187 words
A method for liquid chromatographic analysis which comprises separating and analyzing an enantiomer mixture of a compound having an --NH-- group, a --CONH-- group, or an --OCO-- group bonded to an asymmetric carbon atom thereof by using a packing material for chromatographic use comprising an inorganic carrier having hydroxyl groups at the surface thereof having grafted thereon an α-arylalkylamine derivative which is formed by bonding an optically active α-arylkalkylamine and an aminoalkylsilane through a dibasic carboxylic acid, wherein the grafted α-arylalkylamine derivative is an organosilane represented by general formula (I): ##STR10## 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 proviso that at least one thereof is an alkoxyl group or a halogen atom; R 4 is an alkyl group; Ar is a naphthyl group, which may be substituted; X is --NHCO-- or --N.sup.⊕ H 3 .O.sup.⊖ CO--; Y is a lower alkylene group or a phenylene group; n is an integer of from 2 to 4; and * indicates an asymmetric carbon atom.
Claim 9
Dependent Claim
23 words
A method for analysis as claimed in claim 6, wherein said inorganic carrier having hydroxyl groups at the surface thereof is silica gel.
Claim 10
Dependent Claim
23 words
A method for analysis as claimed in claim 7, wherein the α-arylalkylamine residue in general formula (I) is an optically active 1-(α-naphthyl)ethylamine residue.
Claim 11
Dependent Claim
25 words
A method for analysis as claimed in claim 7, wherein the aminoalkylsilane residue in general formula (I) is an ω-aminopropyltriethoxysilane residue or an ω-aminopropyltrichlorosilane residue.
Claim 12
Dependent Claim
29 words
A method for analysis as claimed in claim 9, wherein the dibasic carboxylic acid residue in general formula (I) is a succinic acid residue or a terephthalic acid residue.
References Cited (Backward Citations)
US4322310A
Cited
US4324681A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-08-04 | 1990-02-03 | 1990-08-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-08-04 | 1994-02-03 | 1994-08-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-08-04 | 1998-02-03 | 1998-08-05 | $7700.00 | Window Closed / Lapsed |