Skip to main content
Top

2023 | OriginalPaper | Chapter

Novel Hemocompatible Thiol-yne Based Photopolymers Obtained by the Advanced Stereolithography (SLA) Processing with Strongly Improved Surface Smoothness by a Novel Exposition Approach for Anti-aliasing

Authors : Roman Major, Marcin Surmiak, Maciej Gawlikowski, Romana Schwarz, Marcin Kot, Justyna Wiecek, Juergen M. Lackner

Published in: Innovations in Biomedical Engineering

Publisher: Springer International Publishing

Activate our intelligent search to find suitable subject content or patents.

search-config
loading …

Abstract

Purpose The purpose of the work was the developed new photosensitive material dedicated for the blood contact in particular blood pump components.
Material Comparable to the thiol-ene polymerization, the thiol-yne reaction follows a step growth mechanism bringing unique properties to this interesting class of materials. Polymerization shrinkage is low, and oxygen inhibition plays only a minor role due to efficient hydrogen abstraction of peroxy radicals from thiols under the simultaneous formation of highly reactive thiyl radicals. One challenging issue of thiol-based formulations is their shelf-life. Dark reactions of thiol, methacrylate and yne, catalysed from basic impurities or traces of metal ions and peroxides, can lead to a significant increase in viscosity during storage time. In order to enable a stable printing of the desired 3D structures, appropriate stabilizers must be found.
Methodology Expression of platelet activation markers was measured on CD61 gated objects using PAC-1 antibody for conformational change of glycoprotein IIb/IIIa, and using CD62P for P-selectin. Integrated fluorescence of the activation marker was calculated as a multiplication total of geometric mean fluorescence by percentage of marker-positive objects. Both platelet receptors activation was calculated as measured by PAC-1 and P-selectin (CD62) expression: percentage and mean channel fluorescence of CD62-positive platelets (% and MNF, respectively). The biocompatible resin system, thiol-yne reactive monomers have been evaluated. This reaction is based on a multiple step radical mechanism and finally leads to an addition of two thiol units to one yne functionality forming corresponding thio-ether bonds.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Springer Professional "Wirtschaft"

Online-Abonnement

Mit Springer Professional "Wirtschaft" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 340 Zeitschriften

aus folgenden Fachgebieten:

  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Versicherung + Risiko




Jetzt Wissensvorsprung sichern!

Literature
1.
go back to reference ASTM International (2018) ASTM D6110 - 18 Standard Test Method for Determining the Charpy Impact Resistance of Notched Specimens of Plastics ASTM International (2018) ASTM D6110 - 18 Standard Test Method for Determining the Charpy Impact Resistance of Notched Specimens of Plastics
2.
go back to reference ASTM International (2018) ASTM D648-18 Standard Test Method for Deflection Temperature of Plastics Under Flexural Load in the Edgewise Position ASTM International (2018) ASTM D648-18 Standard Test Method for Deflection Temperature of Plastics Under Flexural Load in the Edgewise Position
3.
go back to reference Bader H, Cross LC, Heilbron I, Jones ERH (1949) Researches on acetylenic compounds Part XVIII. The addition of thiolacetic acid to acetylenic hydrocarbons. The conversion of monosubstituted acetylenes into aldehydes and 1:2-dithiols. J Chem Soc (Resumed) Bader H, Cross LC, Heilbron I, Jones ERH (1949) Researches on acetylenic compounds Part XVIII. The addition of thiolacetic acid to acetylenic hydrocarbons. The conversion of monosubstituted acetylenes into aldehydes and 1:2-dithiols. J Chem Soc (Resumed)
4.
go back to reference Bader H The addition of thiolacetic acid to ethynylcarbinols and the conversion of the adducts into aldols and -unsaturated aldehydes. J Chem Soc (Resumed) 116–121 Bader H The addition of thiolacetic acid to ethynylcarbinols and the conversion of the adducts into aldols and -unsaturated aldehydes. J Chem Soc (Resumed) 116–121
5.
go back to reference Brummelhuis N, Schlaad H (2011) Stimuli-responsive star polymers through thiol-yne core functionalization/crosslinking of block copolymer micelles. Polym Chem 2(5):1180CrossRef Brummelhuis N, Schlaad H (2011) Stimuli-responsive star polymers through thiol-yne core functionalization/crosslinking of block copolymer micelles. Polym Chem 2(5):1180CrossRef
6.
go back to reference Chen G, Kumar J, Gregory A, Stenzel MH (2009) Efficient synthesis of dendrimers via a thiol-yne and esterification process and their potential application in the delivery of platinum anti-cancer drugs. Chem Commun 41:6291–3CrossRef Chen G, Kumar J, Gregory A, Stenzel MH (2009) Efficient synthesis of dendrimers via a thiol-yne and esterification process and their potential application in the delivery of platinum anti-cancer drugs. Chem Commun 41:6291–3CrossRef
7.
go back to reference Choi T, Yeo S, Song J-G, Seo S, Jang B, Kim S-H et al (2018) Hydrogen plasma-enhanced atomic layer deposition of hydrogenated amorphous carbon thin films. Surf Coatings Technol 344:12–20CrossRef Choi T, Yeo S, Song J-G, Seo S, Jang B, Kim S-H et al (2018) Hydrogen plasma-enhanced atomic layer deposition of hydrogenated amorphous carbon thin films. Surf Coatings Technol 344:12–20CrossRef
8.
go back to reference EN ISO 75 (2013) EN ISO 75 Kunststoffe - Bestimmung der Wärmeformbeständigkeitstemperatur EN ISO 75 (2013) EN ISO 75 Kunststoffe - Bestimmung der Wärmeformbeständigkeitstemperatur
9.
go back to reference EN ISO 179 (2010) DIN EN ISO 179 Kunststoffe - Bestimmung der Charpy-Schlageigenschaften EN ISO 179 (2010) DIN EN ISO 179 Kunststoffe - Bestimmung der Charpy-Schlageigenschaften
10.
go back to reference Esfandiari P, Ligon SC, Lagref JJ, Frantz R, Cherkaoui Z, Liska R (2013) Efficient stabilization of thiol-ene formulations in radical photopolymerization. J Polym Sci Part A Polym Chem. 51:4261–4266CrossRef Esfandiari P, Ligon SC, Lagref JJ, Frantz R, Cherkaoui Z, Liska R (2013) Efficient stabilization of thiol-ene formulations in radical photopolymerization. J Polym Sci Part A Polym Chem. 51:4261–4266CrossRef
11.
go back to reference Fairbanks BD, Scott TF, Kloxin CJ, Anseth KS, Bowman CN (2009) Thiol-Yne photopolymerizations: novel mechanism, kinetics, and step-growth formation of highly cross-linked networks. Macromolecules 42(1):211–217CrossRef Fairbanks BD, Scott TF, Kloxin CJ, Anseth KS, Bowman CN (2009) Thiol-Yne photopolymerizations: novel mechanism, kinetics, and step-growth formation of highly cross-linked networks. Macromolecules 42(1):211–217CrossRef
12.
go back to reference Hartlieb M et al (2017) Well-defined hyperstar copolymers based on a thiol-yne hyperbranched core and a poly(2-oxazoline) shell for biomedical applications. Polym Chem 8(13):2041–2054CrossRef Hartlieb M et al (2017) Well-defined hyperstar copolymers based on a thiol-yne hyperbranched core and a poly(2-oxazoline) shell for biomedical applications. Polym Chem 8(13):2041–2054CrossRef
13.
go back to reference Hensarling RM, Doughty VA, Chan JW, Patton DL (2009) Polymer brushes with thiol-yne chemistry: indoors and out. J Am Chem Soc 131(41):14673–14675CrossRef Hensarling RM, Doughty VA, Chan JW, Patton DL (2009) Polymer brushes with thiol-yne chemistry: indoors and out. J Am Chem Soc 131(41):14673–14675CrossRef
14.
go back to reference Hoogenboom R (2010) Thiol-yne chemistry: a powerful tool for creating highly functional materials. Angewandte Chemie Int Edn 49(20):3415–7CrossRef Hoogenboom R (2010) Thiol-yne chemistry: a powerful tool for creating highly functional materials. Angewandte Chemie Int Edn 49(20):3415–7CrossRef
15.
go back to reference Houdkova J, Branecky M, Plichta T, Jiricek P, Zemek J, Cech V (2018) Chemical depth profile of layered a-CSiO: H nanocomposites. Appl Surf Sci 456:941–950CrossRef Houdkova J, Branecky M, Plichta T, Jiricek P, Zemek J, Cech V (2018) Chemical depth profile of layered a-CSiO: H nanocomposites. Appl Surf Sci 456:941–950CrossRef
16.
go back to reference King DM, Liang X, Burton BB, Kamal Akhtar M, Weimer AW (2008) Passivation of pigment-grade TiO2 particles by nanothick atomic layer deposited SiO2 films. Nanotechnology 19:255604CrossRef King DM, Liang X, Burton BB, Kamal Akhtar M, Weimer AW (2008) Passivation of pigment-grade TiO2 particles by nanothick atomic layer deposited SiO2 films. Nanotechnology 19:255604CrossRef
17.
go back to reference Kobayashi E, Yoshino T, Aoshima S, Furukawa J (1995) Addition polymerization of 2-cyano-1,4-benzenedithiol to 1,4-diethynylbenzene and properties of polymers. J Polym Sci Part A Polym Chem 33(14):2403 Kobayashi E, Yoshino T, Aoshima S, Furukawa J (1995) Addition polymerization of 2-cyano-1,4-benzenedithiol to 1,4-diethynylbenzene and properties of polymers. J Polym Sci Part A Polym Chem 33(14):2403
18.
go back to reference Konkolewicz D, Gray-Weale A, Perrier S (2009) Hyperbranched polymers by thiol-yne chemistry: from small molecules to functional polymers. J Am Chem Soc 131(50):18075–18077 Konkolewicz D, Gray-Weale A, Perrier S (2009) Hyperbranched polymers by thiol-yne chemistry: from small molecules to functional polymers. J Am Chem Soc 131(50):18075–18077
19.
go back to reference Konkolewicz D et al (2011) Luminescent hyperbranched polymers: combining thiol-yne chemistry with gold-mediated C-H bond activation. Organometallics 30(6):1315–1318 Konkolewicz D et al (2011) Luminescent hyperbranched polymers: combining thiol-yne chemistry with gold-mediated C-H bond activation. Organometallics 30(6):1315–1318
20.
go back to reference Konkolewicz D, Poon CK, Gray-Weale A, Perrier S (2011) Hyperbranched alternating block copolymers using thiol-yne chemistry: materials with tuneable properties. Chem Commun 47(1):239–241 Konkolewicz D, Poon CK, Gray-Weale A, Perrier S (2011) Hyperbranched alternating block copolymers using thiol-yne chemistry: materials with tuneable properties. Chem Commun 47(1):239–241
21.
go back to reference Lang M, Schade A, Bräse S (2016) Synthesis of three-dimensional porous hyper-crosslinked polymers via thiol-yne reaction. Beilstein J Organ Chem 12:2570–2576 Lang M, Schade A, Bräse S (2016) Synthesis of three-dimensional porous hyper-crosslinked polymers via thiol-yne reaction. Beilstein J Organ Chem 12:2570–2576
22.
go back to reference Lee J, Jang W, Kim H, Shin S, Kweon Y, Lee K et al (2018) Characteristics of low SiOC films deposited via atomic layer deposition. Thin Solid Films 645:334–339 Lee J, Jang W, Kim H, Shin S, Kweon Y, Lee K et al (2018) Characteristics of low SiOC films deposited via atomic layer deposition. Thin Solid Films 645:334–339
23.
go back to reference Lowe AB, Bowman CN (2013) Thiol-X chemistries in polymer and materials surface. RSC Publishing Lowe AB, Bowman CN (2013) Thiol-X chemistries in polymer and materials surface. RSC Publishing
24.
go back to reference Lowe AB, Hoyle CE, Bowman CN (2010) Thiol-yne click chemistry: a powerful and versatile methodology for materials synthesis. J Mater Chem 20(23):4745 Lowe AB, Hoyle CE, Bowman CN (2010) Thiol-yne click chemistry: a powerful and versatile methodology for materials synthesis. J Mater Chem 20(23):4745
25.
go back to reference Lowe AB (2014) Thiol-yne ‘click’/coupling chemistry and recent applications in polymer and materials synthesis and modification. Polymer 55(22):5517–5549 Lowe AB (2014) Thiol-yne ‘click’/coupling chemistry and recent applications in polymer and materials synthesis and modification. Polymer 55(22):5517–5549
26.
go back to reference Ma Z, Brown S, Howe JY, Overbury SH, Dai S (2008) Surface modification of Au/TiO2 catalysts by SiO2 via atomic layer deposition. J Phys Chem C 112:9448–9457 Ma Z, Brown S, Howe JY, Overbury SH, Dai S (2008) Surface modification of Au/TiO2 catalysts by SiO2 via atomic layer deposition. J Phys Chem C 112:9448–9457
27.
go back to reference March J (1985) Advanced organic chemistry: reactions, mechanisms, and structure, 3rd edn. Wiley, New York March J (1985) Advanced organic chemistry: reactions, mechanisms, and structure, 3rd edn. Wiley, New York
28.
go back to reference Nagasawa H, Yamaguchi Y (1994) Mechanisms of SiC growth by alternate supply of SiH2Cl2 and C2H2. Appl Surf Sci 82–83:405–409 Nagasawa H, Yamaguchi Y (1994) Mechanisms of SiC growth by alternate supply of SiH2Cl2 and C2H2. Appl Surf Sci 82–83:405–409
29.
go back to reference Naik SS, Chan JW, Comer C, Hoyle CE, Savin DA (2011) Thiol-yne “click” chemistry as a route to functional lipid mimetics. Polym Chem 2(2):303–305 Naik SS, Chan JW, Comer C, Hoyle CE, Savin DA (2011) Thiol-yne “click” chemistry as a route to functional lipid mimetics. Polym Chem 2(2):303–305
30.
go back to reference Oesterreicher A, Wiener J, Roth M, Moser A, Gmeiner R, Edler M et al (2016) Tough and degradable photopolymers derived from alkyne monomers for 3D printing of biomedical materials. Polym Chem 7:5169–5180 Oesterreicher A, Wiener J, Roth M, Moser A, Gmeiner R, Edler M et al (2016) Tough and degradable photopolymers derived from alkyne monomers for 3D printing of biomedical materials. Polym Chem 7:5169–5180
31.
go back to reference Ohashi T, Kobayashi E, Jinbo T, Furukawa J (1997) The crystal structure of 1,4-benzenedithiol by rietveld analysis and studies on the mechanism of solid-state addition polymerization of 1,4-benzenedithiol to 1,4-diethynylbenzene. J Polym Sci Part A Polym Chem 35(9):1621 Ohashi T, Kobayashi E, Jinbo T, Furukawa J (1997) The crystal structure of 1,4-benzenedithiol by rietveld analysis and studies on the mechanism of solid-state addition polymerization of 1,4-benzenedithiol to 1,4-diethynylbenzene. J Polym Sci Part A Polym Chem 35(9):1621
32.
go back to reference Ovanesyan RA, Hausmann DM, Agarwal S (2017) Challenges in atomic layer deposition of carbon-containing silicon-based dielectrics. J Vac Sci Technol Vac Surf Film 35:021506 Ovanesyan RA, Hausmann DM, Agarwal S (2017) Challenges in atomic layer deposition of carbon-containing silicon-based dielectrics. J Vac Sci Technol Vac Surf Film 35:021506
33.
go back to reference Sadayuki E, Imai S, Matsumura M (1995) Sub-atomic layer growth of SiC at low temperatures. Jpn J Appl Phys 34:6166 Sadayuki E, Imai S, Matsumura M (1995) Sub-atomic layer growth of SiC at low temperatures. Jpn J Appl Phys 34:6166
34.
go back to reference Semsarilar M, Ladmiral V, Perrier S (2010) Highly branched and hyperbranched glycopolymers via reversible addition-fragmentation chain transfer polymerization and click chemistry. Macromolecules 43(3):1438 Semsarilar M, Ladmiral V, Perrier S (2010) Highly branched and hyperbranched glycopolymers via reversible addition-fragmentation chain transfer polymerization and click chemistry. Macromolecules 43(3):1438
35.
go back to reference Yao B et al (2014) Catalyst-free thiol-yne click polymerization: a powerful and facile tool for preparation of functional poly(vinylene sulfide)s. Macromolecules 47(4):1325–1333 Yao B et al (2014) Catalyst-free thiol-yne click polymerization: a powerful and facile tool for preparation of functional poly(vinylene sulfide)s. Macromolecules 47(4):1325–1333
36.
go back to reference Yao B, Sun JQ, AnJun T, Ben Z (2010) Thiol-yne click polymerization. Chin Sci Bull 58(22):2711–2718 Yao B, Sun JQ, AnJun T, Ben Z (2010) Thiol-yne click polymerization. Chin Sci Bull 58(22):2711–2718
37.
go back to reference Ye S, Cramer NB, Smith IR, Voigt KR, Bowman CN (2011) Reaction kinetics and reduced shrinkage stress of thiol-yne-methacrylate and thiol-yne-acrylate ternary systems. Macromolecules 44:9084–9090 Ye S, Cramer NB, Smith IR, Voigt KR, Bowman CN (2011) Reaction kinetics and reduced shrinkage stress of thiol-yne-methacrylate and thiol-yne-acrylate ternary systems. Macromolecules 44:9084–9090
38.
go back to reference Yu B, Chan JW, Hoyle CE, Lowe AB (2009) Sequential thiol-ene/thiol-ene and thiol-ene/thiol-yne reactions as a route to well-defined mono and bis end-functionalized poly(N-isopropylacrylamide). J Polym Sci Part A Polym Chem 47(14):3544 Yu B, Chan JW, Hoyle CE, Lowe AB (2009) Sequential thiol-ene/thiol-ene and thiol-ene/thiol-yne reactions as a route to well-defined mono and bis end-functionalized poly(N-isopropylacrylamide). J Polym Sci Part A Polym Chem 47(14):3544
39.
go back to reference Zhou WZ, Zheng H, Li Y, Liu H, Li Y (2010) Synthesis of sulfuric macrocycles and a rotaxane through thiol-yne click and dithiol coupling reactions. Org Lett 12(18):4078–4081 Zhou WZ, Zheng H, Li Y, Liu H, Li Y (2010) Synthesis of sulfuric macrocycles and a rotaxane through thiol-yne click and dithiol coupling reactions. Org Lett 12(18):4078–4081
Metadata
Title
Novel Hemocompatible Thiol-yne Based Photopolymers Obtained by the Advanced Stereolithography (SLA) Processing with Strongly Improved Surface Smoothness by a Novel Exposition Approach for Anti-aliasing
Authors
Roman Major
Marcin Surmiak
Maciej Gawlikowski
Romana Schwarz
Marcin Kot
Justyna Wiecek
Juergen M. Lackner
Copyright Year
2023
DOI
https://doi.org/10.1007/978-3-030-99112-8_21