Irgacure 2959-functionalized poly(ethyleneimine)s as improved photoinitiators: enhanced water solubility, migration stability and visible-light operation
Two novel water soluble polymeric photoinitiators (PPIs) (PEI-I2959 and PEI-I2959-Ts) for free radical polymerization have been synthesized by introducing 2-hydroxy-4′-(2-hydroxyethoxy)-2-methylpropiophenone (Irgacure 2959 or I2959) functionality into branched poly(ethyleneimine) ( M w = 1800 g mol...
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| Veröffentlicht in: | Polymer chemistry 2021-05, Vol.12 (18), p.2772-2785 |
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| creator | Eren, Tugce Nur Kariksiz, Neslihan Demirci, Gozde Tuncel, Duygu Okte, Neren Yagci Acar, Havva Avci, Duygu |
| description | Two novel water soluble polymeric photoinitiators (PPIs) (PEI-I2959 and PEI-I2959-Ts) for free radical polymerization have been synthesized by introducing 2-hydroxy-4′-(2-hydroxyethoxy)-2-methylpropiophenone (Irgacure 2959 or I2959) functionality into branched poly(ethyleneimine) (
M
w
= 1800 g mol
−1
). These PPIs show an excellent water-solubility of 35-45 g L
−1
, thus exceeding the solubility of I2959 by 7-9-fold. PPIs show strong absorbance at 274 nm (
∼ 2-3 times larger than that of I2959); and less prominent peaks at 320 and 380 nm for PEI-I2959 and PEI-I2959-Ts, respectively, in water. The aza-Michael addition (∼10% conversion) and high photopolymerization efficiencies (90-100% conversion) under both UV and visible light are obtained by photo-differential scanning calorimetry (photo-DSC) and Real-Time Fourier Transform Infrared (RT-FTIR) spectroscopy. The photopolymerization mechanisms involve charge transfer complex formation, verified by absorption studies and enabling visible light polymerization; and a Type I mechanism. PEI-I2959-Ts exhibits 8 times higher migration stability than I2959 due to its high molecular weight. In tests against NIH/3T3 and L929 mouse embryonic fibroblast cells using the MTT cell viability assay, the non-cytotoxicity of PEI-I2959-Ts is shown and PEI-I2959 shows reasonable cell viability at lower concentrations, indicating that PPIs have potential usage in biomaterials.
I2959-functionalized PEI based PPIs with 7-9 times higher water solubility than I2959, visible light activation, dual-curing properties and migration stability were synthesized. |
| doi_str_mv | 10.1039/d1py00298h |
| format | Article |
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M
w
= 1800 g mol
−1
). These PPIs show an excellent water-solubility of 35-45 g L
−1
, thus exceeding the solubility of I2959 by 7-9-fold. PPIs show strong absorbance at 274 nm (
∼ 2-3 times larger than that of I2959); and less prominent peaks at 320 and 380 nm for PEI-I2959 and PEI-I2959-Ts, respectively, in water. The aza-Michael addition (∼10% conversion) and high photopolymerization efficiencies (90-100% conversion) under both UV and visible light are obtained by photo-differential scanning calorimetry (photo-DSC) and Real-Time Fourier Transform Infrared (RT-FTIR) spectroscopy. The photopolymerization mechanisms involve charge transfer complex formation, verified by absorption studies and enabling visible light polymerization; and a Type I mechanism. PEI-I2959-Ts exhibits 8 times higher migration stability than I2959 due to its high molecular weight. In tests against NIH/3T3 and L929 mouse embryonic fibroblast cells using the MTT cell viability assay, the non-cytotoxicity of PEI-I2959-Ts is shown and PEI-I2959 shows reasonable cell viability at lower concentrations, indicating that PPIs have potential usage in biomaterials.
I2959-functionalized PEI based PPIs with 7-9 times higher water solubility than I2959, visible light activation, dual-curing properties and migration stability were synthesized.</description><identifier>ISSN: 1759-9954</identifier><identifier>EISSN: 1759-9962</identifier><identifier>DOI: 10.1039/d1py00298h</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Biocompatibility ; Biomedical materials ; Charge transfer ; Complex formation ; Conversion ; Fourier transforms ; Free radical polymerization ; Free radicals ; Photoinitiators ; Photopolymerization ; Polyethyleneimine ; Polymer chemistry ; Polymerization ; Solubility ; Stability ; Toxicity</subject><ispartof>Polymer chemistry, 2021-05, Vol.12 (18), p.2772-2785</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-971d0f91ba5204f97f1b8715729320bf6bac3b961f77ed442a2e439835916b293</citedby><cites>FETCH-LOGICAL-c281t-971d0f91ba5204f97f1b8715729320bf6bac3b961f77ed442a2e439835916b293</cites><orcidid>0000-0001-5601-8814 ; 0000-0002-9927-0291</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Eren, Tugce Nur</creatorcontrib><creatorcontrib>Kariksiz, Neslihan</creatorcontrib><creatorcontrib>Demirci, Gozde</creatorcontrib><creatorcontrib>Tuncel, Duygu</creatorcontrib><creatorcontrib>Okte, Neren</creatorcontrib><creatorcontrib>Yagci Acar, Havva</creatorcontrib><creatorcontrib>Avci, Duygu</creatorcontrib><title>Irgacure 2959-functionalized poly(ethyleneimine)s as improved photoinitiators: enhanced water solubility, migration stability and visible-light operation</title><title>Polymer chemistry</title><description>Two novel water soluble polymeric photoinitiators (PPIs) (PEI-I2959 and PEI-I2959-Ts) for free radical polymerization have been synthesized by introducing 2-hydroxy-4′-(2-hydroxyethoxy)-2-methylpropiophenone (Irgacure 2959 or I2959) functionality into branched poly(ethyleneimine) (
M
w
= 1800 g mol
−1
). These PPIs show an excellent water-solubility of 35-45 g L
−1
, thus exceeding the solubility of I2959 by 7-9-fold. PPIs show strong absorbance at 274 nm (
∼ 2-3 times larger than that of I2959); and less prominent peaks at 320 and 380 nm for PEI-I2959 and PEI-I2959-Ts, respectively, in water. The aza-Michael addition (∼10% conversion) and high photopolymerization efficiencies (90-100% conversion) under both UV and visible light are obtained by photo-differential scanning calorimetry (photo-DSC) and Real-Time Fourier Transform Infrared (RT-FTIR) spectroscopy. The photopolymerization mechanisms involve charge transfer complex formation, verified by absorption studies and enabling visible light polymerization; and a Type I mechanism. PEI-I2959-Ts exhibits 8 times higher migration stability than I2959 due to its high molecular weight. In tests against NIH/3T3 and L929 mouse embryonic fibroblast cells using the MTT cell viability assay, the non-cytotoxicity of PEI-I2959-Ts is shown and PEI-I2959 shows reasonable cell viability at lower concentrations, indicating that PPIs have potential usage in biomaterials.
I2959-functionalized PEI based PPIs with 7-9 times higher water solubility than I2959, visible light activation, dual-curing properties and migration stability were synthesized.</description><subject>Biocompatibility</subject><subject>Biomedical materials</subject><subject>Charge transfer</subject><subject>Complex formation</subject><subject>Conversion</subject><subject>Fourier transforms</subject><subject>Free radical polymerization</subject><subject>Free radicals</subject><subject>Photoinitiators</subject><subject>Photopolymerization</subject><subject>Polyethyleneimine</subject><subject>Polymer chemistry</subject><subject>Polymerization</subject><subject>Solubility</subject><subject>Stability</subject><subject>Toxicity</subject><issn>1759-9954</issn><issn>1759-9962</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpF0ctKxDAUBuAiCg7jbNwLATcqVnPpLe5kvA0M6EIXrkraJtMMaVOTdKS-iW9rxsqYzTkkHwfOnyA4RvAKQUKvK9QNEGKa1XvBBKUxDSlN8P6uj6PDYGbtGvpDUIRJMgm-F2bFyt5wgKlHom9LJ3XLlPziFei0Gs64qwfFWy4b2fJzC5gFsumM3mxBrZ2WrXSSOW3sDeBtzdrSv3wyxw2wWvWFVNINl6CRK8O2w4F1bLwErK3ARlpZKB4quaod0B0f1VFwIJiyfPZXp8Hbw_3r_ClcPj8u5rfLsMQZciFNUQUFRQWLMYwETQUqshTFKaYEw0IkBStJQRMk0pRXUYQZ5hGhGYkpSgqPpsHpONev9NFz6_K17o1PwOY4xpFXKcVeXYyqNNpaw0XeGdkwM-QI5tv08zv08v6b_pPHJyM2tty5_98hPxLbhHc</recordid><startdate>20210514</startdate><enddate>20210514</enddate><creator>Eren, Tugce Nur</creator><creator>Kariksiz, Neslihan</creator><creator>Demirci, Gozde</creator><creator>Tuncel, Duygu</creator><creator>Okte, Neren</creator><creator>Yagci Acar, Havva</creator><creator>Avci, Duygu</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0001-5601-8814</orcidid><orcidid>https://orcid.org/0000-0002-9927-0291</orcidid></search><sort><creationdate>20210514</creationdate><title>Irgacure 2959-functionalized poly(ethyleneimine)s as improved photoinitiators: enhanced water solubility, migration stability and visible-light operation</title><author>Eren, Tugce Nur ; Kariksiz, Neslihan ; Demirci, Gozde ; Tuncel, Duygu ; Okte, Neren ; Yagci Acar, Havva ; Avci, Duygu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-971d0f91ba5204f97f1b8715729320bf6bac3b961f77ed442a2e439835916b293</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Biocompatibility</topic><topic>Biomedical materials</topic><topic>Charge transfer</topic><topic>Complex formation</topic><topic>Conversion</topic><topic>Fourier transforms</topic><topic>Free radical polymerization</topic><topic>Free radicals</topic><topic>Photoinitiators</topic><topic>Photopolymerization</topic><topic>Polyethyleneimine</topic><topic>Polymer chemistry</topic><topic>Polymerization</topic><topic>Solubility</topic><topic>Stability</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Eren, Tugce Nur</creatorcontrib><creatorcontrib>Kariksiz, Neslihan</creatorcontrib><creatorcontrib>Demirci, Gozde</creatorcontrib><creatorcontrib>Tuncel, Duygu</creatorcontrib><creatorcontrib>Okte, Neren</creatorcontrib><creatorcontrib>Yagci Acar, Havva</creatorcontrib><creatorcontrib>Avci, Duygu</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Polymer chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Eren, Tugce Nur</au><au>Kariksiz, Neslihan</au><au>Demirci, Gozde</au><au>Tuncel, Duygu</au><au>Okte, Neren</au><au>Yagci Acar, Havva</au><au>Avci, Duygu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Irgacure 2959-functionalized poly(ethyleneimine)s as improved photoinitiators: enhanced water solubility, migration stability and visible-light operation</atitle><jtitle>Polymer chemistry</jtitle><date>2021-05-14</date><risdate>2021</risdate><volume>12</volume><issue>18</issue><spage>2772</spage><epage>2785</epage><pages>2772-2785</pages><issn>1759-9954</issn><eissn>1759-9962</eissn><abstract>Two novel water soluble polymeric photoinitiators (PPIs) (PEI-I2959 and PEI-I2959-Ts) for free radical polymerization have been synthesized by introducing 2-hydroxy-4′-(2-hydroxyethoxy)-2-methylpropiophenone (Irgacure 2959 or I2959) functionality into branched poly(ethyleneimine) (
M
w
= 1800 g mol
−1
). These PPIs show an excellent water-solubility of 35-45 g L
−1
, thus exceeding the solubility of I2959 by 7-9-fold. PPIs show strong absorbance at 274 nm (
∼ 2-3 times larger than that of I2959); and less prominent peaks at 320 and 380 nm for PEI-I2959 and PEI-I2959-Ts, respectively, in water. The aza-Michael addition (∼10% conversion) and high photopolymerization efficiencies (90-100% conversion) under both UV and visible light are obtained by photo-differential scanning calorimetry (photo-DSC) and Real-Time Fourier Transform Infrared (RT-FTIR) spectroscopy. The photopolymerization mechanisms involve charge transfer complex formation, verified by absorption studies and enabling visible light polymerization; and a Type I mechanism. PEI-I2959-Ts exhibits 8 times higher migration stability than I2959 due to its high molecular weight. In tests against NIH/3T3 and L929 mouse embryonic fibroblast cells using the MTT cell viability assay, the non-cytotoxicity of PEI-I2959-Ts is shown and PEI-I2959 shows reasonable cell viability at lower concentrations, indicating that PPIs have potential usage in biomaterials.
I2959-functionalized PEI based PPIs with 7-9 times higher water solubility than I2959, visible light activation, dual-curing properties and migration stability were synthesized.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d1py00298h</doi><tpages>14</tpages><orcidid>https://orcid.org/0000-0001-5601-8814</orcidid><orcidid>https://orcid.org/0000-0002-9927-0291</orcidid></addata></record> |
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| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Biocompatibility Biomedical materials Charge transfer Complex formation Conversion Fourier transforms Free radical polymerization Free radicals Photoinitiators Photopolymerization Polyethyleneimine Polymer chemistry Polymerization Solubility Stability Toxicity |
| title | Irgacure 2959-functionalized poly(ethyleneimine)s as improved photoinitiators: enhanced water solubility, migration stability and visible-light operation |
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