US5154853A
Expired / Lapsed
US
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Unimolecular micelles and method of making the same
Assignee: University of South Florida
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Filing: 1991-02-19
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Granted: 1992-10-13
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Expires: 2011-02-19
Abstract
Abstract In accordance with the present invention there is provided a method of making a cascade polymer including the steps of alkylating the branches of a multi-branch core alkyne building block including multiple ether side chains and simultaneously reducing the alkyne triple bonds and deprotecting to form a multi-hydroxyl terminated, multi-branched all alkyl polymer. The inventive method results in the formation of a unimolecular micelle consisting essentially of alkyl carbon.
Inventors
- 👤 George R. Newkome
- 👤 Charles Moorefield
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 18:01
CPC Classifications
C; C08; C08G; C08G83/00; C08G83/002; C08G83/003; A; A61; A61K; A61K47/00; A61K47/50; A61K47/69; A61K47/6905; A61K47/6907; C07; C07C; C07C17/00; C07C17/093; C07C17/16; C07C43/00; C07C43/02; C07C43/03; C07C43/14; C07C43/164; C07C43/166; C08G61/00; C08G85/00; C09; C09K; C09K23/00; Y; Y10; Y10S; Y10S516/00; Y10S516/01; Y10S516/06
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
49 words
A method of making a cascade polymer includes the steps of: alkylating the branches of a multi-branched core alkyl compound with a terminal alkyne building block including multiple ethereal side chains, and simultaneously reducing the alkyne triple bonds and deprotecting to form a multihydroxyl terminated multi-branched all alkyl polymer.
Claim 2
Independent Claim
49 words
A method of making a cascade polymer includes the steps of: alkylating the branches of a multi-branched core alkyl compound with a terminal alkyne building block including multiple ethereal side chains, and simultaneously reducing the alkyne triple bonds and deprotecting to form a multihydroxyl terminated multi-branched all alkyl polymer.
Claim 3
Dependent Claim
27 words
A method as set forth in claim 1 wherein said alkylating, reducing, and deprotecting steps are sequentially repeated to increase the size of the all alkyl polymer.
Claim 4
Dependent Claim
25 words
A method as set forth in claim 2 further including the step of oxidizing the multihydroxyl terminations to increase the water solubility of the polymer.
Claim 5
Dependent Claim
34 words
A method as set forth in claim 3 wherein said oxidizing step is further defined as oxidizing the multihydroxyl termination in the presence of RuO 4 NaIO 4 and forming a multi-carboxylate branched polymer.
Claim 6
Dependent Claim
26 words
A method as set forth in claim 1 wherein said alkylating step is further defined as alkylating in the presence of hexamethylphosphoramide, lithium diisopropylamide and tetramethylethylemidiamine.
Claim 7
Dependent Claim
24 words
A method as set forth in claim 1 wherein said deprotecting step is further defined as deprotecting in the presence of Pd-C under hydrogen.
Claim 8
Dependent Claim
29 words
A method as set forth in claim 1 wherein the core alkyl compound includes halogenated side chains, said alkylating step being further defined as alkylating the halogenated side chains.
Claim 9
Dependent Claim
36 words
A method as set forth in claim 7 wherein said sequential repeating step is further defined as transforming to a better leaving group each of the multihydroxyl branches and then alkylating each of the transformed branches.
Claim 10
Dependent Claim
23 words
A method as set forth in claim 8 wherein in said transforming step is further defined as brominating each of the multihydroxyl branches.
Claim 11
Dependent Claim
44 words
A method as set forth in claim 1 wherein the core alkyl compound is a tetrabromide alkyl core compound, said alkylating step being further defined as alkylating the core compound with four equivalents for the terminal alkyne building block and forming a dodecabenzyl ether.
Claim 12
Dependent Claim
21 words
A method as set forth in claim 10 wherein said reducing and deprotecting steps are further defined as forming a dodecaalcohol.
Claim 13
Dependent Claim
40 words
A method as set forth in claim 11 further including the steps of converting the dodecaalcohol to a dodecabromide in the presence of SOBr 2 and initiating further elongation of the branches by repeating said alkylating, reducing, and deprotecting steps.
Claim 14
Dependent Claim
22 words
A method as set forth in claim 1 further including the steps of deriving the terminal alkyne building block from a nitrotriol.
Claim 15
Dependent Claim
25 words
A method as set forth in claim 13 wherein said deriving step is further defined as deriving the terminal alkyne building block from 4-nitro-4-[1-(hydroxypropyl)]-1,7-heptanediol (I).
Claim 16
Dependent Claim
97 words
A method as set forth in claim 13 wherein said deriving step is further defined as treating (I) with benzyl chloride to form a tris ether (II), cyanoethylating (II) to form a cyanotris (benzylether) (III), hydrolyzing the nitrile of (III) to derive a carboxylic acid (IV), converting the acid (IV) to an alcohol (V) with excess BH 3 -THF solution transforming (V) to a chloride (VI) in CH 2 Cl 2 with excess thionyl chloride and a catalytic-amount of pyridine, reacting (VI) with lithium acetylide ethylenediamine complex in Me 2 SO to derive a terminal alkyne (VII).
Claim 17
Dependent Claim
21 words
A method as set forth in claim 13 further including the step of synthesizing the core alkyl compound from a nitrotriol.
Claim 18
Dependent Claim
23 words
A method as set forth in claim 16 wherein said synthesizing step is further defined as synthesizing the core alkyl compound from (I).
Claim 19
Dependent Claim
61 words
A method as set forth in claim 16 wherein said synthesizing step is further defined as treating I with benzyl chloride to form II, cyanoethylating II to form III, hydrolyzing the nitrile of III to derive IV, converting IV to V with excess BH 3 -THF solution, and brominating V with HBr/H 2 SO 4 to synthesize the core alkyl tetrabromide.
Claim 20
Dependent Claim
40 words
A method as set forth in claim 1 further including the step of modifying the CN, CO 2 R or --COR, wherein R is selected from the group consisting of H, alkyl, alkaryl, aryl ammonium, sulfonium, phosphonium and metal salt.
Claim 21
Dependent Claim
23 words
A method as set forth in claim 1 further including the steps of bonding mono-, di-, and tri-valent metals to said multihydroxyl terminations.
Claim 22
Dependent Claim
27 words
A method as set forth in claim 1 wherein the polymer has a predetermined porosity, said method including the step of changing the porosity of the polymer.
Claim 23
Dependent Claim
37 words
A method as set forth in claim 21 wherein each of the core alkyl compound and terminal alkyne building blocks define a quaternary center, said changing step is further defined as changing the distances between quaternary centers.
Claim 24
Dependent Claim
27 words
A method as set forth in claim 1 further including the step of incorporating chirality either in a core or on the surface creating a chiral sphere.
Claim 25
Dependent Claim
17 words
An unimolecular micelle consisting essentially of a carbon core atom and essentially all alkyl arms extending therefrom.
Claim 26
Dependent Claim
17 words
An unimolecular micelle consisting essentially of a carbon core atom and essentially all alkyl arms extending therefrom.
Claim 27
Dependent Claim
21 words
A micelle as set forth in claim 24 wherein said micelle consists essentially of multibranched all alkyl arms having hydroxyl terminations.
Claim 28
Dependent Claim
21 words
A micelle as set forth in claim 24 wherein said micelle consists essentially of multi-branched all alkyl arms having carboxyl terminations.
Claim 29
Dependent Claim
17 words
A micelle as set forth in claim 24 including a mono-, di-, or tri-valent metal bonded thereto.
Claim 30
Dependent Claim
33 words
A micelle as set forth in claim 24 wherein each of said branches includes an N, O, S, or P bonded thereto thereby permitting the inclusion of metals or organics into said core.
Claim 31
Dependent Claim
69 words
A unimolecular micelle having the formula ##STR6## wherein R 1 is an alkyl having C3 to C20, R 2 is an alkyl having C3 to C20, R 3 is selected from the group consisting of --CONH 2 , --COC1, CHO, --CN, --CO 2 R 4 , --COR 4 , and R 4 is selected from the group consisting of H, alkyl, alkaryl, aryl, ammonium, sulfonium phosphonium and metal salt.
Claim 32
Dependent Claim
69 words
A unimolecular micelle having the formula ##STR6## wherein R 1 is an alkyl having C3 to C20, R 2 is an alkyl having C3 to C20, R 3 is selected from the group consisting of --CONH 2 , --COC1, CHO, --CN, --CO 2 R 4 , --COR 4 , and R 4 is selected from the group consisting of H, alkyl, alkaryl, aryl, ammonium, sulfonium phosphonium and metal salt.
Claim 33
Dependent Claim
73 words
A unimolecular micelle having the formula ##STR7## wherein R 1 is a perfluoroalkyl having C3-C20, R 2 is a perfluoroalkyl having C 3 to C 2- , R 3 is selected from the group consisting of F, CF 3 , CONH 2 , COC1, CHO, CN, CO 2 R 4 , and R 4 is selected from the group consisting of F, CF 3 perfluoroalkyl, perfluoroalkaryl, perfluoroaryl ammonium, sulfonium, phosphonium and metal salt.
Claim 34
Dependent Claim
73 words
A unimolecular micelle having the formula ##STR7## wherein R 1 is a perfluoroalkyl having C3-C20, R 2 is a perfluoroalkyl having C 3 to C 2- , R 3 is selected from the group consisting of F, CF 3 , CONH 2 , COC1, CHO, CN, CO 2 R 4 , and R 4 is selected from the group consisting of F, CF 3 perfluoroalkyl, perfluoroalkaryl, perfluoroaryl ammonium, sulfonium, phosphonium and metal salt.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-10-13 | 1996-04-13 | 1996-10-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-10-13 | 2000-04-13 | 2000-10-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-10-13 | 2004-04-13 | 2004-10-13 | $7700.00 | Window Closed / Lapsed |