Synthesis and cellular compatibility of multi-block biodegradable poly(ε-caprolactone)-based polyurethanes

Ferdous Khan, Simon Valere, Steven Fuhrmann, Valeria Arrighi, Mark Bradley

Research output: Contribution to journalArticle

Abstract

A library of block copolymers was synthesized by varying the molecular weight of the poly(epsilon-caprolactone) (PCL)-diol soft segment (M-w = 850, 3050, 3700 or 7000), which was reacted with methylene diphenyl diisocyanate (MDI), 1,4-phenylene diisocyanate (PDI), 1,1'-methylenebis(4-isocyanatocyclohexane) (HMDI), or 2,4-toluene diisocyanate (TDI) with 1,4-butanediol (BD) or ethylene glycol (EG) added as chain extenders. Thermal and X-ray measurements indicated that the crystalline structure of the copolymers was largely dependent on the chain length of the PCL-diol, with no crystallization taking place with the smallest diol (M-w = 850) using MDI, TDI or HMDI. However, the copolymers produced from a PCL-diol (M-w = 850) and PDI and chain extenders (BD or EG) showed resolved crystalline peaks while no peaks appeared with other diisocyanates. Hydrolytic degradation studies demonstrated a faster degradation rate in the case of more amorphous copolymers than semi-crystalline copolymers. The cellular compatibility of the copolymers was evaluated by fabricating the entire library of polymers in a microarray format and in vitro cell culture, demonstrating that all the 57 copolymers supported cellular attachment and growth.

Original languageEnglish
Pages (from-to)2590-2600
Number of pages11
JournalJournal of Materials Chemistry B
Volume1
Issue number20
Early online date19 Mar 2013
DOIs
Publication statusPublished - 2013

Fingerprint

Polyurethanes
Copolymers
Toluene 2,4-Diisocyanate
Ethylene Glycol
Crystalline materials
Butylene Glycols
Degradation
Microarrays
Crystallization
Chain length
Cell culture
Block copolymers
polycaprolactone
Polymers
Molecular weight
X rays

Keywords

  • STRUCTURE-PROPERTY RELATIONSHIPS
  • RING-OPENING POLYMERIZATION
  • EPSILON-CAPROLACTONE
  • DEGRADATION BEHAVIOR
  • DRUG-DELIVERY
  • DIISOCYANATE
  • COPOLYMERS
  • SCAFFOLDS
  • CELLS
  • ELASTOMERS

Cite this

Khan, Ferdous ; Valere, Simon ; Fuhrmann, Steven ; Arrighi, Valeria ; Bradley, Mark. / Synthesis and cellular compatibility of multi-block biodegradable poly(ε-caprolactone)-based polyurethanes. In: Journal of Materials Chemistry B. 2013 ; Vol. 1, No. 20. pp. 2590-2600.
@article{e75a82d130bd4603a751c059af670f73,
title = "Synthesis and cellular compatibility of multi-block biodegradable poly(ε-caprolactone)-based polyurethanes",
abstract = "A library of block copolymers was synthesized by varying the molecular weight of the poly(epsilon-caprolactone) (PCL)-diol soft segment (M-w = 850, 3050, 3700 or 7000), which was reacted with methylene diphenyl diisocyanate (MDI), 1,4-phenylene diisocyanate (PDI), 1,1'-methylenebis(4-isocyanatocyclohexane) (HMDI), or 2,4-toluene diisocyanate (TDI) with 1,4-butanediol (BD) or ethylene glycol (EG) added as chain extenders. Thermal and X-ray measurements indicated that the crystalline structure of the copolymers was largely dependent on the chain length of the PCL-diol, with no crystallization taking place with the smallest diol (M-w = 850) using MDI, TDI or HMDI. However, the copolymers produced from a PCL-diol (M-w = 850) and PDI and chain extenders (BD or EG) showed resolved crystalline peaks while no peaks appeared with other diisocyanates. Hydrolytic degradation studies demonstrated a faster degradation rate in the case of more amorphous copolymers than semi-crystalline copolymers. The cellular compatibility of the copolymers was evaluated by fabricating the entire library of polymers in a microarray format and in vitro cell culture, demonstrating that all the 57 copolymers supported cellular attachment and growth.",
keywords = "STRUCTURE-PROPERTY RELATIONSHIPS, RING-OPENING POLYMERIZATION, EPSILON-CAPROLACTONE, DEGRADATION BEHAVIOR, DRUG-DELIVERY, DIISOCYANATE, COPOLYMERS, SCAFFOLDS, CELLS, ELASTOMERS",
author = "Ferdous Khan and Simon Valere and Steven Fuhrmann and Valeria Arrighi and Mark Bradley",
year = "2013",
doi = "10.1039/c3tb00358b",
language = "English",
volume = "1",
pages = "2590--2600",
journal = "Journal of Materials Chemistry B",
issn = "2050-750X",
publisher = "Royal Society of Chemistry",
number = "20",

}

Synthesis and cellular compatibility of multi-block biodegradable poly(ε-caprolactone)-based polyurethanes. / Khan, Ferdous; Valere, Simon; Fuhrmann, Steven; Arrighi, Valeria; Bradley, Mark.

In: Journal of Materials Chemistry B, Vol. 1, No. 20, 2013, p. 2590-2600.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis and cellular compatibility of multi-block biodegradable poly(ε-caprolactone)-based polyurethanes

AU - Khan, Ferdous

AU - Valere, Simon

AU - Fuhrmann, Steven

AU - Arrighi, Valeria

AU - Bradley, Mark

PY - 2013

Y1 - 2013

N2 - A library of block copolymers was synthesized by varying the molecular weight of the poly(epsilon-caprolactone) (PCL)-diol soft segment (M-w = 850, 3050, 3700 or 7000), which was reacted with methylene diphenyl diisocyanate (MDI), 1,4-phenylene diisocyanate (PDI), 1,1'-methylenebis(4-isocyanatocyclohexane) (HMDI), or 2,4-toluene diisocyanate (TDI) with 1,4-butanediol (BD) or ethylene glycol (EG) added as chain extenders. Thermal and X-ray measurements indicated that the crystalline structure of the copolymers was largely dependent on the chain length of the PCL-diol, with no crystallization taking place with the smallest diol (M-w = 850) using MDI, TDI or HMDI. However, the copolymers produced from a PCL-diol (M-w = 850) and PDI and chain extenders (BD or EG) showed resolved crystalline peaks while no peaks appeared with other diisocyanates. Hydrolytic degradation studies demonstrated a faster degradation rate in the case of more amorphous copolymers than semi-crystalline copolymers. The cellular compatibility of the copolymers was evaluated by fabricating the entire library of polymers in a microarray format and in vitro cell culture, demonstrating that all the 57 copolymers supported cellular attachment and growth.

AB - A library of block copolymers was synthesized by varying the molecular weight of the poly(epsilon-caprolactone) (PCL)-diol soft segment (M-w = 850, 3050, 3700 or 7000), which was reacted with methylene diphenyl diisocyanate (MDI), 1,4-phenylene diisocyanate (PDI), 1,1'-methylenebis(4-isocyanatocyclohexane) (HMDI), or 2,4-toluene diisocyanate (TDI) with 1,4-butanediol (BD) or ethylene glycol (EG) added as chain extenders. Thermal and X-ray measurements indicated that the crystalline structure of the copolymers was largely dependent on the chain length of the PCL-diol, with no crystallization taking place with the smallest diol (M-w = 850) using MDI, TDI or HMDI. However, the copolymers produced from a PCL-diol (M-w = 850) and PDI and chain extenders (BD or EG) showed resolved crystalline peaks while no peaks appeared with other diisocyanates. Hydrolytic degradation studies demonstrated a faster degradation rate in the case of more amorphous copolymers than semi-crystalline copolymers. The cellular compatibility of the copolymers was evaluated by fabricating the entire library of polymers in a microarray format and in vitro cell culture, demonstrating that all the 57 copolymers supported cellular attachment and growth.

KW - STRUCTURE-PROPERTY RELATIONSHIPS

KW - RING-OPENING POLYMERIZATION

KW - EPSILON-CAPROLACTONE

KW - DEGRADATION BEHAVIOR

KW - DRUG-DELIVERY

KW - DIISOCYANATE

KW - COPOLYMERS

KW - SCAFFOLDS

KW - CELLS

KW - ELASTOMERS

U2 - 10.1039/c3tb00358b

DO - 10.1039/c3tb00358b

M3 - Article

VL - 1

SP - 2590

EP - 2600

JO - Journal of Materials Chemistry B

JF - Journal of Materials Chemistry B

SN - 2050-750X

IS - 20

ER -