Crosslinking of Polylactide by High Energy Irradiation and Photo-Curing
Abstract
:1. Introduction
2. PLA Crosslinking by Electron Beam or Gamma Irradiation
3. Photo-Crosslinked PLA
4. PLA-Based Materials by Photo- and High Energy Radiation Crosslinking
5. Conclusions
Author Contributions
Funding
Conflicts of Interest
References
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Polylactide-Based Polymer (Mn, g·mol−1) | Radiation Type, Dose | Curing Co-Agent | Gel Content, % | Achieved Results | Reference |
---|---|---|---|---|---|
PLLA (99,000) | Electron beam, 0–100 kGy | TAIC, TMAIC, TMPTA, TMPTMA, HDDA, derivative of EG | 0.1–88 | Together with annealing improved heat stability above Tg until Tm; lower solubility in any solvents; retarded enzymatic degradation. | [30] |
PLLA | Electron beam, 0–50 kGy | TAIC, TMAIC, TMPTA, TMPTMA, HDDA, derivative of EG | 10–83 | Stability at higher melting temperature; application of the crosslinked PLLA on heat-shrinkable tubes, cups and plates. | [31] |
PLLA (115,100), PDLLA (197,000) | Electron beam, 0–50 kGy | TAIC | ~40–100 | Shifts of Tcc to higher and Tm to lower temperatures; increase in tensile strength, young’s modulus and decrease in elongation at break; the crosslinked PLA samples were harder and more brittle at low temperature, but rubbery and soft, then stable at higher temperature (over Tm); decreased rate of enzymatic hydrolysis. | [32] |
Equimolar blend of PLLA and PDLA | Electron beam, 0–50 kGy | TAIC + supercritical CO2 | ~30–90 | Shift of Tm of homo crystals to lower temp.; improved toughness and tensile strength. | [33] |
PLLA (155,500) | Electron beam 0–90 kGy | TAIC | NA | Pristine PLA: Only degradation was observed; PLA/TAIC: Increase of Tg (69–75 °C), decrease of melt flow and water vapor permeability. | [35] |
PLA (155,500) | Electron beam, 200–1000 kGy | TAIC | 68.2–89.4 | For neat PLA: only degradation; PLA/TAIC: decrease of gel content with increasing radiation dose; optimum crosslinking obtained at radiation dose of 40–200 kGy and 3–5 wt % of TAIC. | [25] |
PLA (155,500) /PCL (82,500) blend | Electron beam, 0–90 kGy | TAIC | NA | PLA: Increase of flexural modulus, tensile strength, flexural strength, decrease of elongation at break; PLA/PCL blend: partial degradation of PLA phase, mechanical properties depending on ratios of the polymeric components. | [34] |
PLA (91,000)/PBAT (35,000) blend | Electron beam, 0–90 kGy | TAIC | 40–90 | Crosslinking and degradation after irradiation mostly in PLA phase, PBAT less susceptible to radiation influence. | [39,40] |
PLLA + Reinforced by flax fiber (20 wt %) | Electron beam, 0–40kGy | TAIC | 7.6–62.5 | Increase of tensile strength of about 20% in the presence of TAIC at 40kGy of irradiation dose; irradiation in the presence of TAIC led to reduced enzymatic degradation; decrease of interfacial adhesion of flax fibers and PLA matrix in the presence of TAIC. | [41] |
PLA (210,000) + MMT (1,3,5 wt %) | Electron beam, 1 and 10 kGy | - | NA | Increase of Tg, crystallinity and young modulus, decrease of elongation at brake and oxygen permeability. | [42] |
PLA/PEGM/HBN blend composite | Electron beam, 0–100 kGy | - | NA | At low doses: partial branching and crosslinking for neat PLA and PLA/PEGM; at higher doses: chain scission dominates. increase of Tg, notched impact strength and heat deflection temp. with radiation of blend-composites with higher amount of HBN; accelerated hydrolytic degradation of irradiated blend and blend-composites. | [43] |
PLLA | γ-rays 2.5–50 kGy | TAIC | 10–100 | Decrease of swelling with increasing gel content, decrease in elongation (75%), maintenance of tensile strength, decrease of crystallinity (from 36 to 10%) and Tm (from 182 to 165 °C). | [36] |
PLA + Flax fiber (5 wt %) | γ-rays 0–20 kGy | TAIC | 70–90 | Increase of the gel fraction in PLA/ flax composite with the radiation dose, degradation at higher doses; improvement of tensile strength and toughness with the increase in the radiation dose, decrease of elongation at break. | [37] |
PLA (106,000) | γ-rays 0–100 kGy | TAIC, Ov-POSS | Up to 80 | Higher degree of crosslinking for PLA/OvPOSS in comparison to PLA/TAIC; irradiated composites exhibited decrease of crystallinity, lower elongation at break and higher E-modulus, higher thermal stability and heat deflection temp. than that of neat PLA | [44] |
PLA (72,000) | γ-rays 0–20 kGy | TAIC as crosslinking agent (CA), Epoxy functional acrylic oligomer (Joncryl® ADR 4368) as chain extender (CE) | 1.2–46.2 | Considerable gel formation was observed for PLA/CA at high irradiation dose; addition of CA or CE increased the shear viscosity of neat and irradiated PLA; addition of CA and CE enhanced Tc and decreased crystallinity; improvement of tensile properties was higher for CA. | [38] |
PLA Structure (Mn, g·mol−1) | Crosslinking Group | Photoinitiator | Gel Content a, % | Achieved Results | Ref. |
---|---|---|---|---|---|
PDLLA-b-PEG-b-PDLLA (1000–20,000) | Acrylate end group | 2,2-dimethoxy-2-phenylacetophenone (Irgacure 651) | 65–74 | Degradation rate increased with increasing Mn of precursor; materials used in the sustained release of proteins. | [48] |
PDLLA-b-PEG-b-PDLLA Or: P(DLLA-co-TMC)-b-PEG-b-P(DLLA-co-TMC (4500–5500) | Fumarate end group | 2,2-dimethoxy-2-phenylacetophenone | >90 | Hydrogels prepared in N-vinylpyrrolidone were used for the study of model protein release; the degradation behavior could be controlled by changing the composition of the hydrophobic segments. | [49] |
PDLLA-b-PEG-b-PDLLA (~1600) | Acrylate end group | 2,2-dimethoxy-2-phenyl acetophenone | Preparation of porous scaffolds for the study of the growth factor encapsulation and release and implantation in the case of cranial defect. | [50] | |
PDLLA-b-PEG-b-PDLLA (990–1240) | Acrylate end group | camphorquinone/ethyl-4-N,N-dimethylaminobenzoate | 89–100 | Modification of hydrophobicity (contact angle 123°–142°); Tg = 1.8–26 °C depending on the composition and crosslinking density; tensile modulus in the range 0.92–3.67 MPa and strain at break 0.19–0.65; preparation of scaffolds with various pore sizes by salt-leaching method. | [52] |
PDLLA-b-PEG-b-PDLLA (1120–10,720) | Acrylate end group | 2,2-dimethoxy-2-phenylacetophenone | 78–100 | Both lower crosslinking density (higher Mn of macromer) and the lower crystallinity (lower Mn) increased the degradation rate of the networks; the maximum improvement in penetration force, lubricant property, over control was 41% in the needle coated with PPG-based polymer network. | [53] |
PDLLA-b-PPG-b-PDLLA (1150–4720) | Acrylate end group | 2,2-dimethoxy-2-phenylacetophenone | 93–99 | ||
PDLLA-b-PTMG-b-PDLLA (1370–3620) | Acrylate end group | 2,2-dimethoxy-2-phenylacetophenone | 95–97 | ||
PDLLA-b-PCL (1570–2390) | Methacrylate end group | camphorquinone/ethyl-4-dimethylaminobenzoate | Highly crosslinked | Decrease of Tg with increasing CL content (Tg in the range −30 to 60 °C). Storage moduli in the glassy regime were similar, in the rubbery regime dependent on crosslinking density; highly cross-linked scaffolds were cellularly compatible and promoted osteoblast attachment. | [51] |
P(CL-co-LLA-co-GA) (1870–10,190) | Acrylate end group | 2,2-dimethoxy-2-phenylacetophenone | >95 | Increase of Tg of 2.8–14.9 °C, similar ultimate strength (σ = 2.39–3.76 MPa); Young’s modulus (E = 1.66–12.29 MPa and maximum strain (ε = 21–176%); Excellent biocompatibility of films with smooth muscle cells. | [54] |
P(LDLA-co-GA)-b-PEG-b- P(LDLA-co-GA) (~5300) | Itaconic end groups | camphorquinone | 94–98 b | Swelling properties depended on crosslinking time, thus crosslinking density; with longer UV exposure better hydrolytic stability of hydrogel was observed. | [55] |
P(DLLA-co-TMC) (27,000–29,000) | Methacrylate end group | Irgacure 2959 | 74–90 | Depending on the DLLA /TMC ratio, amorphous networks with Tg of 13 to 51 °C and elastic modulus from 3.6 MPa to 2.7 GPa were obtained; networks of more than 40 mol% of TMC are tough, flexible and elastomeric at r.t. with elongations at break of up to 800%. When DLLA:TMC = 60:40, Tg is between 25 and 37 °C, thus elastic medical devices with SM properties could be implanted in a temporary shape. | [56] |
2,3- and 6-arm PDLLA (6600–34,200) | Methacrylate end group | 2-hydroxy-1-[4- (hydroxyethoxy)phenyl]-2-methyl-1-propanone (Irgacure 2959) | 96 | Tg (55–76 °C) dependent on macromer chain length; mechanical properties similar to HMW PDLLA- suitable for stereolithography; mouse pre-osteoblasts readily adhered and proliferated well on networks. | [57] |
3-arm P(TMC-co-DLLA) (3100–4000) | Fumaric acid monoethyl ester | 2,2-dimethoxy-2-phenylacetophenone | 67–81c | The E modulus decrease with TMC content, tensile strength and elongation at break unaffected. Relative low values of tensile strength (1–2 MPa), and E modulus (1–10 MPa) in comparison with HMW PDLLA and PTMC. | [58] |
4-arm PDLLA-co-PCL (5000–10,000) | Acrylate end group | 1-hydroxycyclohexylphenylketone (irgacure 184) | NA | Fabrication of microstructures by soft lithography. Possibility of using studied materials to culture mammalian cells. | [59] |
4-arm P(LLA-b-CL) (Mn ~3200–12,000) | Methacrylate end group | Camphorquinone d | NA | Transition temperatures depended on the length of poly-CL segments. Decrease of Tm and crystallinity with increasing Mn. Thermo-responsive properties as permeability of a drug. | [60] |
3-arm P(CL-co-DLLA) (1250–7800) | Acrylate end group | 2,2-dimethoxy-2-phenylacetophenone | >95 | Tg of elastomers below physiological temperature (even below 0 °C). The Young’s modulus and stress at break inversely proportional but strain at break-proportional to the prepolymer Mn. The ability of elastomeric devices to encapsulate (glyco)proteins and release them according to an osmotic pressure delivery mechanism; confirmed ability to degradation in vitro and in vivo. Preparation of porous scaffolds capable to degradation with mechanical properties dependent on prepolymers Mn. Ability to adsorb proteins and to cell proliferation; dependence of adsorbed protein layer on the material stiffness. | [87,88,89,90,91,92] |
3-arm poly(CL-co- DLLA) (1250, 2700 and 3900) | Acrylate end group and co-photo-crosslinker poly(ethylene glycol)diacrylate (PEGDA) (4000 and 24,000) | 2,2-dimethoxy-2-phenylacetophenone | 95–98 | Tg, Tm and ∆Hf varied with prepolymer Mn, co-photo-crosslinker amount and Mn. Networks without PEGDA were amorphous, with PEGDA indicated melting; preparation of cylindrical elastomeric devices able to encapsulate Vitamin B12. | [64] |
3-arm poly(TMC-co-DLLA) (7800–8500) | Acrylate end group | 2,2-dimethoxy-2-phenylacetophenone | 79–88 | With increasing amount of DLLA increase of Young’s, stress at break, Tg and decrease of elongation at break. The possibility of osmotic pressure driven release of proteins. Study of the behavior of elastomers implanted into rats. | [93,94] |
3-arm poly(TMC-DLLA-CL) (2300–7800) | Acrylate end group and co-photo-crosslinker poly(ethylene glycol)diacrylate (PEGDA) | 2,2-dimethoxy-2-phenylacetophenone | 86–99 | Tg (−18 to 2 °C) varied with the monomer composition and the Mn of PEGDA. Preparation of cylindrical elastomeric devices able to swell and to encapsulate corticosteroid and growth factors utilizing the osmotic pressure mechanism. | [65,66,67] |
Poly(LLA-co- CL-acryolyl carbonate) (17,900–22,600) | Pendant acrylate group | 2,2-dimethoxy-2-phenylacetophenone | 90 | Preparation of fibrous scaffolds by melt electrospinning writing; Stiffness of the scaffolds increased significantly (up to ∼10-fold) after crosslinking with UV compared with un-crosslinked scaffolds; the preservation of stiffness upon repetitive loading. | [62] |
Poly(L-lactide-co-acryolyl carbonate) (55,900–72,100) | Pendant acrylate group | NA | 84–94 | Increase of Tg, decrease of Tm and degree of crystallinity after crosslinking; Electrospun and photo-crosslinked polymer resulted in scaffolds with increased tensile modulus in comparison with uncrosslinked fibrous scaffolds; good cytocompatibility toward fibroblasts of crimp-stabilized scaffolds. | [63] |
3-arm Poly(DLLA-co-CL) (Mw 4800–10,900) | Acrylate end group and co-photo-crosslinker N-methacrylated glycol chitosan (MGC) | Irgacure 2959 | 98–100 | Preparation of bi-continuous two-phase (elastomer /hydrogel) cell delivery device for the repair and/or replacement of load-bearing soft tissues. Decrease of elastic modulus with increasing content of MGC; using electrospinning for scaffold preparation. | [95,96,97] |
3-arm Poly(DLLA-co-CL) (2700 and 5000) | Acrylate end group and co-photo-crosslinker diacrylate oligo(d,l-lactide)-b-poly(ethylene glycol)-b-oligo(d,l-lactide) | 2,2-dimethoxy-2-phenylacetophenone | >95 | Enhancing the degradation rate by introducing PEG fragment; regulation of the degradation rate and peptide release by Mn of PEG and Mn of prepolymer. | [98] |
4-arm PDLLA (1500–9500) | Methacrylate end group (methacrylic anhydride or 2-isocyanatoethyl methacrylate) | 2,2-dimethoxy-2-phenylacetophenone | 90–99 | Increasing of Tg with decreasing Mn of precursors; networks based on low Mn oligomers were generally more rigid, those based on high Mn exhibited higher elongation; mechanical properties differ with type of precursors methacrylate end group. | [68] |
PDLLA (1310) + TEGDMA as reactive diluent + Hydroxyapatite (HA) as bioactive filler | Methacrylate end group | Camphorquinone/ N,N’-dimethylaminoethyl Methacrylate | 77–100 | Tg (38–55 °C), flexural strength (3.5–94 MPa) and flexural modulus (75-3980 MPa) were dependent on composition of polymer resin and an amount of HA; increasing thermal stability with increasing amount of filler. Higher gel content and higher concentration of HA led to decreased rate of degradation; higher HA content resulted in the less cytotoxic sample. | [69] |
4-arm Poly(d,l-lactide) (2600 or 2400 or 450–820) | Methacrylate end group | 4,4′-bis(dimethylamino)benzophenone e | NA | Preparation of scaffolds with Young’s modulus even bigger than 4 GPa for the mesenchymal stem cells osteogenic differentiation; Independently—collagen reinforcement: about one order of magnitude increased Young’s modulus for the hybrid matrix without affecting its cytotoxicity; | [72,73,74,75] |
4-arm Poly(L-lactide) (Mw 1250) | Methacrylate end group | Irgacure 369 e | NA | Preparation of scaffolds for supporting Schwann cell growth—neural scaffolds in nerve repair. | [70] |
Poly(LLA-co-GMA) (1650–3260) | Pendant methacrylate group | Camphorquinone/ N,N′-dimethylaminoethyl methacrylate | 72–95 | With increasing content of GMA (9.5–19.2 mol%) the increase of gel content, compressive stress (3–25.5 MPa) and the decrease of degree of swelling was observed; Increase of Tg by 15–20 °C in comparison with original copolymer. | [76,77] |
PLLA (MV 276,500) | - | Benzophenone | 38–98.5 | Slight increase of Tg in comparison with pristine PLA, decrease of Tm and crystallinity; improvement of thermal stability; with increase of gel fraction—increase of storage modulus (from 5.4 to 9.6 GPa at 0 °C), tensile strength (from 48 to 81 MPa), modulus (from 1.8 to 3.1 GPa), toughness (from 67 to 82 MPa) and decrease of strain (from 3.9 to 1.6%). | [78] |
PLLA - diacyl of 5-cinnamoyloxyisophthalic acid (ICA) (10,000–34,500) | Pendant 3-phenylprop-2-ene group | - | 50–100 | Slight increase of Tg (from 50 to 53 °C), decrease of crystallinity (from 10 to 3 %), slight decreases of Tm, thermal decomposition Td, increase of ultimate tensile strength (from 13 to 23 MPa), decrease in elongation (from 12 to 5.2%), increase of Young’s modulus E (from 483 to 830 MPa); Decrease of degradation rate. | [82] |
PLLA- diacyl of 4,4′-(adipoyldioxy)dicinnamic acid (8700–43,500) f | Main-chain 3-phenylprop-2-ene group | - | 9–86 | Increase of Tg (from 51 to 53 °C); decrease of ∆Hm (from 4.8 to 0.1 J.g−1), small decrease of Tm (from 150 to 147 °C), increase of thermal decomposition Td; increase of tensile strength and tensile modulus and decrease of elongation at break with increasing photocuring time and gel content; decrease of degradation rate. | [83] |
P(LLA-co-MC) (12,900–65,100) f | Pendant phenylprop-2-ene group | - | NA | The kinetic of UV crosslinking was studied by FT IR spectroscopy. | [84] |
PLA50-Pluronic®-PLA50 (50,000-200,000) | -C-H- bond in polymer chain | Aryl-azide group | Up to 55 | Preparation of elastic microfibers (elastic limit–εy up to 182 %) for soft tissues by electrospinning. | [85] |
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Bednarek, M.; Borska, K.; Kubisa, P. Crosslinking of Polylactide by High Energy Irradiation and Photo-Curing. Molecules 2020, 25, 4919. https://doi.org/10.3390/molecules25214919
Bednarek M, Borska K, Kubisa P. Crosslinking of Polylactide by High Energy Irradiation and Photo-Curing. Molecules. 2020; 25(21):4919. https://doi.org/10.3390/molecules25214919
Chicago/Turabian StyleBednarek, Melania, Katarina Borska, and Przemysław Kubisa. 2020. "Crosslinking of Polylactide by High Energy Irradiation and Photo-Curing" Molecules 25, no. 21: 4919. https://doi.org/10.3390/molecules25214919