US4286964A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Polyfunctional epoxides and halohydrins used as bridging groups to bind aromatic amine group-containing alcohols and thiols to hydroxyl bearing substrates
Assignee: Individual
•
Filing: 1979-10-12
•
Granted: 1981-09-01
•
Expires: 1999-10-12
Abstract
Abstract A process for preparing a derivative of an hydroxyl bearing substrate by reacting an hydroxyl bearing substrate with oxirane bearing molecules to produce an oxirane ring bearing substrate; and reacting the oxirane ring with a substituted primary aromatic amine selected from primary aromatic amine alcohols and primary aromatic amine thiols. Among the compositions so produced is a stable modified hydroxyl bearing substrate or hydroxyl bearing sheet having covalently bonded thereto primary aromatic amines which can be diazotized. The diazotized substrate selectively, covalently binds proteins, polypeptides, peptides, nucleic acids, RNA, single stranded DNA, and nucleic acid hybrids.
Inventors
- 👤 Brian S. Seed
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 06:27
CPC Classifications
C; C12; C12P; C12P19/00; C12P19/26; C12P19/28; C12P19/30; C12P19/34; C08; C08B; C08B15/00; C08B15/05; C08B15/06; C12N; C12N11/00; C12N11/02; C12N11/10; C12N11/12
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
85 words
A stable modified hydroxyl bearing substrate comprising substituted phenyl thioether groups having structural units having the general formula: ##STR5## in which HBS comprises a hydroxyl bearing substrate, R is selected from the group consisting of alkyl groups, hydroxyl bearing alkyl groups, aryl groups, alkylaryl groups, alkyl ether groups, hydroxyl bearing alkyl ether groups, aryl ether groups, alkylaryl ether groups, and hydroxyl bearing alkylaryl ether groups; and in which Z is selected from the group consisting of primary amines, diazo chlorides, diazo fluoborates, and diazo fluorophosphates.
Claim 2
Dependent Claim
85 words
A stable modified hydroxyl bearing substrate comprising substituted phenyl thioether groups having structural units having the general formula: ##STR5## in which HBS comprises a hydroxyl bearing substrate, R is selected from the group consisting of alkyl groups, hydroxyl bearing alkyl groups, aryl groups, alkylaryl groups, alkyl ether groups, hydroxyl bearing alkyl ether groups, aryl ether groups, alkylaryl ether groups, and hydroxyl bearing alkylaryl ether groups; and in which Z is selected from the group consisting of primary amines, diazo chlorides, diazo fluoborates, and diazo fluorophosphates.
Claim 3
Dependent Claim
15 words
The modified hydroxyl bearing substrate of claim 1 in which R comprises a methylene group.
Claim 4
Dependent Claim
22 words
The modified hydroxyl bearing substrate of claim 1 in which R comprises a group having the formula --CH.sub.2 --CHOH--CH.sub.2 --O--(CH.sub.2).sub.4 --O--CH.sub.2 --.
Claim 5
Dependent Claim
94 words
A stable modified hydroxyl bearing sheet comprising substituted phenyl groups having structural units having the general formula: ##STR6## in which HBS comprises a hydroxyl bearing substrate, R is selected from the group consisting of alkyl groups, hydroxyl bearing groups, aryl groups, alkylaryl groups, alkyl ether groups, hydroxyl bearing alkyl ether groups, aryl ether groups, alkylaryl ether groups, and hydroxyl bearing alkylaryl ether groups; Y is selected from the group consisting of oxygen and sulfur; and in which Z is selected from the group consisting of primary amines, diazo chlorides, diazo fluoborates, and diazo fluorophosphates.
Claim 6
Dependent Claim
94 words
A stable modified hydroxyl bearing sheet comprising substituted phenyl groups having structural units having the general formula: ##STR6## in which HBS comprises a hydroxyl bearing substrate, R is selected from the group consisting of alkyl groups, hydroxyl bearing groups, aryl groups, alkylaryl groups, alkyl ether groups, hydroxyl bearing alkyl ether groups, aryl ether groups, alkylaryl ether groups, and hydroxyl bearing alkylaryl ether groups; Y is selected from the group consisting of oxygen and sulfur; and in which Z is selected from the group consisting of primary amines, diazo chlorides, diazo fluoborates, and diazo fluorophosphates.
Claim 7
Dependent Claim
15 words
The modified hydroxyl bearing sheet of claim 4 in which R comprises a methylene group.
Claim 8
Dependent Claim
22 words
The modified hydroxyl bearing sheet of claim 4 in which R comprises a group having the formula --CH.sub.2 --CHOH--CH.sub.2 --O--(CH.sub.2).sub.4 --O--CH.sub.2 --.
Claim 9
Dependent Claim
14 words
The modified sheet of claim 4 wherein the sheet is comprised of cellulose paper.
Claim 10
Dependent Claim
15 words
The modified sheet of claim 5 in which the sheet is comprised of cellulose paper.
Claim 11
Dependent Claim
15 words
The modified sheet of claim 6 in which the sheet is comprised of cellulose paper.
Claim 12
Dependent Claim
59 words
A process for preparing a derivative of a hydroxyl bearing substrate comprising the steps of: reacting a hydroxyl bearing substrate with oxirane bearing molecules to produce an oxirane ring bearing substrate; and reacting the oxirane ring bearing substrate with a substituted primary aromatic amine selected from the group consisting of primary aromatic amine alcohols and primary aromatic amine thiols.
Claim 13
Dependent Claim
59 words
A process for preparing a derivative of a hydroxyl bearing substrate comprising the steps of: reacting a hydroxyl bearing substrate with oxirane bearing molecules to produce an oxirane ring bearing substrate; and reacting the oxirane ring bearing substrate with a substituted primary aromatic amine selected from the group consisting of primary aromatic amine alcohols and primary aromatic amine thiols.
Claim 14
Dependent Claim
17 words
The method of claim 10 wherein the hydroxyl bearing substrate is comprised of an hydroxyl bearing sheet.
Claim 15
Dependent Claim
16 words
The method of claim 10 wherein the hydroxyl bearing substrate is comprised of a cellulose paper.
Claim 16
Dependent Claim
59 words
The method of claim 10 wherein the oxirane bearing molecule has a structure having the general formula: ##STR7## in which M is selected from the group consisting of alkyl groups, aryl groups, ether groups, alkyl ether groups, alkyl aryl groups and alkyl aryl ether groups, and n is an integer selected from the group consisting of 0 and 1.
Claim 17
Dependent Claim
33 words
The method of claim 10 wherein the oxirane bearing molecule has a structure having the general formula: ##STR8## in which X represents a halogen selected from the group comprising chlorine, bromine, and iodine.
Claim 18
Dependent Claim
14 words
The method of claim 10 wherein the oxirane bearing molecule is 1,4-butanediol diglycidyl ether.
Claim 19
Dependent Claim
17 words
The method of claim 13 wherein the hydroxyl bearing substrate is comprised of an hydroxyl bearing sheet.
Claim 20
Dependent Claim
16 words
The method of claim 13 wherein the hydroxyl bearing substrate is comprised of a cellulose paper.
Claim 21
Dependent Claim
17 words
The method of claim 14 wherein the hydroxyl bearing substrate is comprised of an hydroxyl bearing sheet.
Claim 22
Dependent Claim
16 words
The method of claim 14 wherein the hydroxyl bearing substrate is comprised of a cellulose paper.
Claim 23
Dependent Claim
14 words
The method of claim 11 wherein the oxirane bearing molecule is 1,4-butanediol diglycidyl ether.
Claim 24
Dependent Claim
13 words
The method of claim 12 wherein the oxirane bearing molecule is 1,4-butanedioldiglycidyl ether.
Claim 25
Dependent Claim
25 words
The method of claim 10 wherein the substituted primary aromatic amine is selected from the group consisting of o-aminophenol, m-aminophenol, p-aminophenol, o-aminothiophenol, m-aminothiolphenol, and p-aminothiophenol.
Claim 26
Dependent Claim
17 words
The method of claim 22 wherein the hydroxyl bearing substrate is comprised of an hydroxyl bearing sheet.
Claim 27
Dependent Claim
16 words
The method of claim 22 wherein the hydroxyl bearing substrate is comprised of a cellulose paper.
Claim 28
Dependent Claim
14 words
The method of claim 22 wherein the oxirane bearing molecule is 1,4-butanediol diglycidyl ether.
Claim 29
Independent Claim
33 words
The method of claims 14, 15, 16, 17, 18, 19, 20, or 21 wherein the substituted primary aromatic amine is selected from the group consisting of o-aminophenol, m-aminophenol, p-aminophenol, o-aminothiophenol, m-aminothiophenol, and p-aminothiophenol.
Claim 30
Independent Claim
76 words
The method of claims 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 comprising the additional steps of diazotizing the primary amine by reaction with a member selected from the group consisting of nitrous acid and acidic solution of sodium nitrite; and stabilizing the diazo groups by conversion in acidic solution to the salt of a weakly nucleophilic anion selected from the group consisting of tetrafluoborate and hexafluorophosphate.
Claim 31
Independent Claim
29 words
The method of claims 11 or 12 wherein the step of covalently bonding the oxirane bearing molecule to the hydroxyl bearing substrate is conducted in a basic aqueous medium.
Claim 32
Dependent Claim
26 words
The method of claim 28 wherein the step of covalently bonding the oxirane bearing molecule to the hydroxyl bearing substrate is conducted by vigorous end-over-end agitation.
Claim 33
Independent Claim
29 words
The method of claims 10, 11 or 12 wherein the step of covalently bonding the oxirane bearing molecule to the hydroxyl bearing substrate is conducted in basic nonaqueous medium.
Claim 34
Dependent Claim
33 words
The method of claim 30 wherein the basic nonaqueous medium comprises a solution of from 0.05 to 0.1 N NaOH in a solvent selected from the group consisting of methanol, ethanol and acetone.
Claim 35
Dependent Claim
45 words
A process for preparing a derivative of an hydroxyl bearing substrate comprising the step of covalently binding a diazotized, modified hydroxyl bearing substrate of claims 1, 4, 7, 8, or 9 with proteins, polypeptides, peptides, nucleic acids, RNA, single stranded DNA, or nucleic acid hybrids.
Claim 36
Dependent Claim
37 words
The modified substrate of claims 1 or 4 wherein the diazotized amine is selectively covalently bound to molecules selected from the group consisting of proteins, polypeptides, peptides, nucleic acids, RNA, single stranded DNA and nucleic acid hybrids.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-08-31 | 1985-03-02 | 1985-09-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-08-31 | 1989-03-02 | 1989-09-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-08-31 | 1993-03-02 | 1993-09-01 | $7700.00 | Window Closed / Lapsed |