US4694044A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Adsorbent
Assignee: Mitsubishi Chemical Corp
•
Filing: 1985-03-06
•
Granted: 1987-09-15
•
Expires: 2005-03-06
Abstract
Abstract A method of adsorbing a substance such as an optically active substance, comprising contacting a solution of the substance in a solvent with an adsorbent consisting of a cross-linked polymer comprising an optically active, synthetic poly(amino acid) represent by the general formula (I): <IMAGE> (I) wherein R stands for an organic group, R' stands for hydrogen or an alkyl group and n is an integer of at least 5, which may be protected at a terminal amino group and a carrier polymer supporting said synthetic poly(amino acid) thereon, said carrier polymer having affinity for said solvent. A method for producing the cross-linked polymer is also described. The adsorbent is especially useful for optical resolution of racemic mixtures.
Inventors
- 👤 Hideaki Kiniwa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 22:50
CPC Classifications
C; C08; C08G; C08G69/00; C08G69/02; C08G69/08; B; B01; B01J; B01J20/00; B01J20/281; B01J20/29; B01J20/30; B01J20/32; B01J20/3202; B01J20/3206; B01J20/3208; B01J20/321; B01J20/3212; B01J20/3231; B01J20/3242; B01J20/3268; B01J20/3272; B01J20/3274; B01J20/328; B01J20/3282; Y; Y10; Y10T; Y10T428/00; Y10T428/249921; Y10T428/249953; Y10T428/31504; Y10T428/31725; Y10T428/3175
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
95 words
A cross-linked, polymeric material which has been reacted with a chemical cross-linking agent comprising a polymer carrier supporting thereon an optically active, synthetic poly(amino acid) represented by the general formula (I): ##STR10## wherein R stands for an organic group, R' stands for hydrogen or an alkyl group and n is an integer of at least 5, and a terminal amino group protected as shown by the general formula (II): ##STR11## wherein R, R' each has the same meaning as above, R" stands for an organic group and m is an integer of at least 4.
Claim 2
Dependent Claim
95 words
A cross-linked, polymeric material which has been reacted with a chemical cross-linking agent comprising a polymer carrier supporting thereon an optically active, synthetic poly(amino acid) represented by the general formula (I): ##STR10## wherein R stands for an organic group, R' stands for hydrogen or an alkyl group and n is an integer of at least 5, and a terminal amino group protected as shown by the general formula (II): ##STR11## wherein R, R' each has the same meaning as above, R" stands for an organic group and m is an integer of at least 4.
Claim 3
Dependent Claim
13 words
An adsorbent formed of a cross-linked, polymeric material as claimed in claim 1.
Claim 4
Dependent Claim
81 words
A cross-linked, polymeric material as claimed in claim 1 and obtained by a process including the steps of: providing an amino group-containing, cross linked polymer carrier, polymerizing an N-carboxy anhydride represented by the general formula: ##STR12## wherein R and R' each have the same meaning as above, in the presence of said carrier serving as an initiator to form a poly(amino acid) supported on said carrier and having terminal amino groups, and protecting the terminal amino groups with an organic group.
Claim 5
Dependent Claim
31 words
A cross-linked, polymeric material as claimed in claim 3, wherein said carrier is a cross-linked chloromethylstyrene-styrene-divinylbenzene copolymer having its chloromethyl group converted into an aminomethyl group or aminoalkylene substituted aminomethyl group.
Claim 6
Dependent Claim
21 words
A cross-linked, polymeric material as claimed in claim 4, wherein said cross-linked chloromethylstyrene-styrene-divinylbenzene copolymer is obtained by chloromethylating of styrene-divinylbenzene copolymer.
Claim 7
Dependent Claim
30 words
A cross-linked, polymeric material as claimed in claim 3, wherein said carrier is a cross-linked acrylamide-methylenebisacrylamide copolymer or a cross-linked glycidylmethacrylate- ethylene glycol dimethacrylate copolymer having introduced thereinto an alkylamine.
Claim 8
Dependent Claim
29 words
A cross-linked, polymeric material as claimed in claim 1, wherein the substituents R has a group selected from --OH, --COOH, --SH, --NH 2 and --SCH 3 and derivatives thereof.
Claim 9
Dependent Claim
15 words
A cross-linked, polymeric material as claimed in claim 7, wherein the group is an amide.
Claim 10
Independent Claim
93 words
A method of producing a cross-linked polymer comprising an optically active, synthetic poly(amino acid) represented by the general formula (I): ##STR13## wherein R stands for an organic group, R' stands for hydrogen or an alkyl group and n is an integer of at least 5, including the steps of: polymerizing an N-carboxy anhydride represented by the following general formula: ##STR14## wherein R and R' have the same meaning as above in the presence of an initiator to obtain a poly(amino acid), and cross-linking the poly(amino acid) in the presence of a cross-linking agent.
Claim 11
Independent Claim
93 words
A method of producing a cross-linked polymer comprising an optically active, synthetic poly(amino acid) represented by the general formula (I): ##STR13## wherein R stands for an organic group, R' stands for hydrogen or an alkyl group and n is an integer of at least 5, including the steps of: polymerizing an N-carboxy anhydride represented by the following general formula: ##STR14## wherein R and R' have the same meaning as above in the presence of an initiator to obtain a poly(amino acid), and cross-linking the poly(amino acid) in the presence of a cross-linking agent.
Claim 12
Dependent Claim
39 words
A method as claimed in claim 9 wherein said initiator is a polyfunctional amine selected from the group consisting of ethylenediamine, hexamethylenediamine and diethylenetriamine, and said crosslinking agent is selected from the group consisting of polyisocyanates and epoxy resins.
Claim 13
Independent Claim
111 words
A method of producing a cross-linked polymer comprising an optically active, synthetic poly(amino acid) represented by the general formula (I): ##STR15## wherein R stands for an organic group, R' stands for hydrogen or an alkyl group and n is an integer of at least 5, including the steps of: polymerizing an N-carboxy anhydride represented by the following general formula: ##STR16## wherein R and R' each have the same meaning as above, in the presence of an initiator to obtain a poly(amino acid), reacting the poly(amino acid) with a polymerizable vinyl group-containing compound to form a macromer having the polymerizable vinyl group, and copolymerizing the macromer with a copolymerizable vinyl group-containing monomer.
Claim 14
Independent Claim
111 words
A method of producing a cross-linked polymer comprising an optically active, synthetic poly(amino acid) represented by the general formula (I): ##STR15## wherein R stands for an organic group, R' stands for hydrogen or an alkyl group and n is an integer of at least 5, including the steps of: polymerizing an N-carboxy anhydride represented by the following general formula: ##STR16## wherein R and R' each have the same meaning as above, in the presence of an initiator to obtain a poly(amino acid), reacting the poly(amino acid) with a polymerizable vinyl group-containing compound to form a macromer having the polymerizable vinyl group, and copolymerizing the macromer with a copolymerizable vinyl group-containing monomer.
Claim 15
Dependent Claim
70 words
A method as claimed in claim 11 wherein said initiator is an amine selected from the group consisting of ethylenediamine, hexamethylene-diamine, diethylenetriamine, n-butyl-amine, n-propylamine and n-hexylamine, said polymerizable vinyl group-containing compound is selected from the group consisting of acrylic acid chloride, glycidylmethacrylate and chloromethylstyrene, and said copolymerizable vinyl group-containing monomer is selected from the group consisting of 2-hydroxyethylmethacrylate, acrylamide, vinyl acetate, glycidylmethacrylate, styrene, methylmethacrylate, divinylbenzene, methylenebis(acrylamide) and ethylene glycol dimethacrylate.
Claim 16
Independent Claim
102 words
A method of producing a cross-linked polymer comprising an optically active, synthetic poly(amino acid) represented by the general formula (I) : ##STR17## wherein R stands for an organic group, R' stands for hydrogen or an alkyl group and n is an integer of at least 5, including the steps of: polymerizing an N-carboxy anhydride represented by the general formula: ##STR18## wherein R and R' each have the same meaning as above, in the presence of an initiator to form a poly(amino acid), and reacting said poly(amino acid) with a cross-linked polymer carrier so that said poly(amino acid) is supported on said carrier.
Claim 17
Independent Claim
102 words
A method of producing a cross-linked polymer comprising an optically active, synthetic poly(amino acid) represented by the general formula (I) : ##STR17## wherein R stands for an organic group, R' stands for hydrogen or an alkyl group and n is an integer of at least 5, including the steps of: polymerizing an N-carboxy anhydride represented by the general formula: ##STR18## wherein R and R' each have the same meaning as above, in the presence of an initiator to form a poly(amino acid), and reacting said poly(amino acid) with a cross-linked polymer carrier so that said poly(amino acid) is supported on said carrier.
Claim 18
Dependent Claim
28 words
A method as claimed in claim 13, wherein said initiator is a monofunctional alkylamine and said carrier has a functional group capable of reacting with an amino group.
Claim 19
Dependent Claim
16 words
A method as claimed in claim 13, wherein said carrier is a glycidylmethacrylate-ethylene glycol dimethacrylate copolymer.
Claim 20
Dependent Claim
61 words
A method of producing a cross-linked, polymeric material as claimed in claim 9, 11 or 13, wherein the cross-linked polymeric material with its poly(amino acid) of the formula (I) has an ester group, and the process further includes converting the ester group of the cross-linked polymeric material to an active ester group, and converting the active ester group to an amide.
Claim 21
Dependent Claim
18 words
A method as claimed in claim 16, wherein the active ester group is cyanoethyl-ester, chloroethylester, trichloroethylester or trifluoro-ethylester.
References Cited (Backward Citations)
US3966839A
Cited
US4105709A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-09-14 | 1991-03-16 | 1991-09-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-09-14 | 1995-03-16 | 1995-09-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-09-14 | 1999-03-16 | 1999-09-15 | $7700.00 | Window Closed / Lapsed |