Synthesis and characterization of polystyrene-poly(ethylene oxide)-heparin block copolymers

I. Vulić, T. Okano, S.W. Kim, Jan Feijen

Research output: Contribution to journalArticleAcademic

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Abstract

A procedure for the preparation of new block copolymers composed of a hydrophobic block of polystyrene, a hydrophilic spacer-block of poly(ethylene oxide) and a bioactive block of heparin was investigated. Polystyrene with one amino group per chain was synthesized by free radical oligomerization of styrene in dimethylformamide, using 2-aminoethanethiol as a chain transfer agent. This amino group was used in the coupling reaction with amino-telechelic poly(ethylene oxide) to produce an AB type diblock copolymer with one amino group per polystyrene (PSt)-poly(ethylene oxide) (PEO) chain. The amino-semitelechelic oligo-styrene was converted into the isocyanate-semitelechelic oligo-styrene using toluene 2,4-diisocyanate and subsequent coupling with H2N-PEO-NH2 afforded AB type block copolymers with terminal amino groups. The coupling of PSt-PEO-NH2 with heparin was performed in a DMF-H2O mixture, first by activating the heparin carboxylic groups with EDC at pH 5.1-5.2 and subsequently reacting the activated carboxylic groups with the amino groups of the PSt-PEO-NH2 at pH 7.5. Depending on the molecular weights of the diblock copolymer used 25-29% w/w heparin was incorporated. These polymers will be further evaluated for their blood-compatibility.
Original languageUndefined
Pages (from-to)381-391
JournalJournal of polymer science. Part A: Polymer chemistry
Volume26
Issue number2
DOIs
Publication statusPublished - 1988

Keywords

  • IR-70859

Cite this

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title = "Synthesis and characterization of polystyrene-poly(ethylene oxide)-heparin block copolymers",
abstract = "A procedure for the preparation of new block copolymers composed of a hydrophobic block of polystyrene, a hydrophilic spacer-block of poly(ethylene oxide) and a bioactive block of heparin was investigated. Polystyrene with one amino group per chain was synthesized by free radical oligomerization of styrene in dimethylformamide, using 2-aminoethanethiol as a chain transfer agent. This amino group was used in the coupling reaction with amino-telechelic poly(ethylene oxide) to produce an AB type diblock copolymer with one amino group per polystyrene (PSt)-poly(ethylene oxide) (PEO) chain. The amino-semitelechelic oligo-styrene was converted into the isocyanate-semitelechelic oligo-styrene using toluene 2,4-diisocyanate and subsequent coupling with H2N-PEO-NH2 afforded AB type block copolymers with terminal amino groups. The coupling of PSt-PEO-NH2 with heparin was performed in a DMF-H2O mixture, first by activating the heparin carboxylic groups with EDC at pH 5.1-5.2 and subsequently reacting the activated carboxylic groups with the amino groups of the PSt-PEO-NH2 at pH 7.5. Depending on the molecular weights of the diblock copolymer used 25-29{\%} w/w heparin was incorporated. These polymers will be further evaluated for their blood-compatibility.",
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author = "I. Vulić and T. Okano and S.W. Kim and Jan Feijen",
year = "1988",
doi = "10.1002/pola.1988.080260204",
language = "Undefined",
volume = "26",
pages = "381--391",
journal = "Journal of polymer science. Part A: Polymer chemistry",
issn = "0887-624X",
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}

Synthesis and characterization of polystyrene-poly(ethylene oxide)-heparin block copolymers. / Vulić, I.; Okano, T.; Kim, S.W.; Feijen, Jan.

In: Journal of polymer science. Part A: Polymer chemistry, Vol. 26, No. 2, 1988, p. 381-391.

Research output: Contribution to journalArticleAcademic

TY - JOUR

T1 - Synthesis and characterization of polystyrene-poly(ethylene oxide)-heparin block copolymers

AU - Vulić, I.

AU - Okano, T.

AU - Kim, S.W.

AU - Feijen, Jan

PY - 1988

Y1 - 1988

N2 - A procedure for the preparation of new block copolymers composed of a hydrophobic block of polystyrene, a hydrophilic spacer-block of poly(ethylene oxide) and a bioactive block of heparin was investigated. Polystyrene with one amino group per chain was synthesized by free radical oligomerization of styrene in dimethylformamide, using 2-aminoethanethiol as a chain transfer agent. This amino group was used in the coupling reaction with amino-telechelic poly(ethylene oxide) to produce an AB type diblock copolymer with one amino group per polystyrene (PSt)-poly(ethylene oxide) (PEO) chain. The amino-semitelechelic oligo-styrene was converted into the isocyanate-semitelechelic oligo-styrene using toluene 2,4-diisocyanate and subsequent coupling with H2N-PEO-NH2 afforded AB type block copolymers with terminal amino groups. The coupling of PSt-PEO-NH2 with heparin was performed in a DMF-H2O mixture, first by activating the heparin carboxylic groups with EDC at pH 5.1-5.2 and subsequently reacting the activated carboxylic groups with the amino groups of the PSt-PEO-NH2 at pH 7.5. Depending on the molecular weights of the diblock copolymer used 25-29% w/w heparin was incorporated. These polymers will be further evaluated for their blood-compatibility.

AB - A procedure for the preparation of new block copolymers composed of a hydrophobic block of polystyrene, a hydrophilic spacer-block of poly(ethylene oxide) and a bioactive block of heparin was investigated. Polystyrene with one amino group per chain was synthesized by free radical oligomerization of styrene in dimethylformamide, using 2-aminoethanethiol as a chain transfer agent. This amino group was used in the coupling reaction with amino-telechelic poly(ethylene oxide) to produce an AB type diblock copolymer with one amino group per polystyrene (PSt)-poly(ethylene oxide) (PEO) chain. The amino-semitelechelic oligo-styrene was converted into the isocyanate-semitelechelic oligo-styrene using toluene 2,4-diisocyanate and subsequent coupling with H2N-PEO-NH2 afforded AB type block copolymers with terminal amino groups. The coupling of PSt-PEO-NH2 with heparin was performed in a DMF-H2O mixture, first by activating the heparin carboxylic groups with EDC at pH 5.1-5.2 and subsequently reacting the activated carboxylic groups with the amino groups of the PSt-PEO-NH2 at pH 7.5. Depending on the molecular weights of the diblock copolymer used 25-29% w/w heparin was incorporated. These polymers will be further evaluated for their blood-compatibility.

KW - IR-70859

U2 - 10.1002/pola.1988.080260204

DO - 10.1002/pola.1988.080260204

M3 - Article

VL - 26

SP - 381

EP - 391

JO - Journal of polymer science. Part A: Polymer chemistry

JF - Journal of polymer science. Part A: Polymer chemistry

SN - 0887-624X

IS - 2

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