Innovation new route for preparation of polyacrylamide bearing urethane group based on one-pot Curtius rearrangement
One-pot combination of Curtius rearrangement and radical polymerization of an acrylamide derivative bearing carbonyl azide group (ACA) was investigated to provide polyacrylamide bearing side-chain isocyanate groups. The one-pot Curtius rearrangement and radical polymerization successfully proceeded...
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| Veröffentlicht in: | Polymer bulletin (Berlin, Germany) Germany), 2023-05, Vol.80 (5), p.4991-5004 |
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| container_title | Polymer bulletin (Berlin, Germany) |
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| creator | Nagai, Daisuke Shmizu, Naoto Takahashi, Riho Yoneyama, Masaru Yamanobe, Takeshi |
| description | One-pot combination of Curtius rearrangement and radical polymerization of an acrylamide derivative bearing carbonyl azide group (ACA) was investigated to provide polyacrylamide bearing side-chain isocyanate groups. The one-pot Curtius rearrangement and radical polymerization successfully proceeded at a low monomer concentration (0.05 mol/L) to avoid cross-linking between the side-chain isocyanate groups. The one-pot conversion of the in situ generated isocyanate groups into the urethane groups succeeded by the excess amount of alcohol to be reacted (100 equivalents to ACA). The one-pot reaction in the presence of various alcohols (methanol, ethanol, propanol, and butanol) proceeded smoothly to provide the polyacrylamide bearing various urethane moieties with number average molecular weights (
M
n
= 1200 ~ 1600) in 63–96% yields. |
| doi_str_mv | 10.1007/s00289-022-04305-z |
| format | Article |
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M
n
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M
n
= 1200 ~ 1600) in 63–96% yields.</description><subject>Acrylamide</subject><subject>Butanol</subject><subject>Carbonyls</subject><subject>Caustic soda</subject><subject>Characterization and Evaluation of Materials</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Complex Fluids and Microfluidics</subject><subject>Crosslinking</subject><subject>Ethanol</subject><subject>Isocyanates</subject><subject>Magnesium</subject><subject>Organic Chemistry</subject><subject>Original Paper</subject><subject>Physical Chemistry</subject><subject>Polyacrylamide</subject><subject>Polymer Sciences</subject><subject>Polymerization</subject><subject>Polymers</subject><subject>Sodium</subject><subject>Soft and Granular Matter</subject><subject>Solvents</subject><subject>Urethane groups</subject><issn>0170-0839</issn><issn>1436-2449</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>AFKRA</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><recordid>eNp9kE1LxDAQhoMouK7-AU8Bz9F8NG1zlMWPhQUveg5pO1277CZ1kiq7v96uFbx5GoZ5n3fgIeRa8FvBeXEXOZelYVxKxjPFNTuckJnIVM5klplTMuOi4IyXypyTixg3fNzzXMxIWnofPl3qgqceviiGIQFtA9IeoXc4XUJL-7Dduxr3W7frGqAVOOz8mg4I6d15oOuR7GnlIjT0SHhgfUh0MWDqhkhxzKPza9iBT5fkrHXbCFe_c07eHh9eF89s9fK0XNyvWK1UnpjRujTC1bkDrXRtnJSyEFVhtCnaGjKdVYJnphFta2Shi7oB4MYpmQudu8yoObmZensMHwPEZDdhQD--tNKIwpSK53pMySlVY4gRobU9djuHeyu4Pdq1k1072rU_du1hhNQExf7oAfCv-h_qG1kif4o</recordid><startdate>20230501</startdate><enddate>20230501</enddate><creator>Nagai, Daisuke</creator><creator>Shmizu, Naoto</creator><creator>Takahashi, Riho</creator><creator>Yoneyama, Masaru</creator><creator>Yamanobe, Takeshi</creator><general>Springer Berlin Heidelberg</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>AFKRA</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>KB.</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><orcidid>https://orcid.org/0000-0003-4205-822X</orcidid></search><sort><creationdate>20230501</creationdate><title>Innovation new route for preparation of polyacrylamide bearing urethane group based on one-pot Curtius rearrangement</title><author>Nagai, Daisuke ; Shmizu, Naoto ; Takahashi, Riho ; Yoneyama, Masaru ; Yamanobe, Takeshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c336t-955891ac6ae535c9a22271b79597fce454b1049d1ff92757cdee09a326156a493</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Acrylamide</topic><topic>Butanol</topic><topic>Carbonyls</topic><topic>Caustic soda</topic><topic>Characterization and Evaluation of Materials</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Complex Fluids and Microfluidics</topic><topic>Crosslinking</topic><topic>Ethanol</topic><topic>Isocyanates</topic><topic>Magnesium</topic><topic>Organic Chemistry</topic><topic>Original Paper</topic><topic>Physical Chemistry</topic><topic>Polyacrylamide</topic><topic>Polymer Sciences</topic><topic>Polymerization</topic><topic>Polymers</topic><topic>Sodium</topic><topic>Soft and Granular Matter</topic><topic>Solvents</topic><topic>Urethane groups</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nagai, Daisuke</creatorcontrib><creatorcontrib>Shmizu, Naoto</creatorcontrib><creatorcontrib>Takahashi, Riho</creatorcontrib><creatorcontrib>Yoneyama, Masaru</creatorcontrib><creatorcontrib>Yamanobe, Takeshi</creatorcontrib><collection>CrossRef</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central</collection><collection>Technology Collection (ProQuest)</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>SciTech Premium Collection</collection><collection>Materials Science Database</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><jtitle>Polymer bulletin (Berlin, Germany)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nagai, Daisuke</au><au>Shmizu, Naoto</au><au>Takahashi, Riho</au><au>Yoneyama, Masaru</au><au>Yamanobe, Takeshi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Innovation new route for preparation of polyacrylamide bearing urethane group based on one-pot Curtius rearrangement</atitle><jtitle>Polymer bulletin (Berlin, Germany)</jtitle><stitle>Polym. Bull</stitle><date>2023-05-01</date><risdate>2023</risdate><volume>80</volume><issue>5</issue><spage>4991</spage><epage>5004</epage><pages>4991-5004</pages><issn>0170-0839</issn><eissn>1436-2449</eissn><abstract>One-pot combination of Curtius rearrangement and radical polymerization of an acrylamide derivative bearing carbonyl azide group (ACA) was investigated to provide polyacrylamide bearing side-chain isocyanate groups. The one-pot Curtius rearrangement and radical polymerization successfully proceeded at a low monomer concentration (0.05 mol/L) to avoid cross-linking between the side-chain isocyanate groups. The one-pot conversion of the in situ generated isocyanate groups into the urethane groups succeeded by the excess amount of alcohol to be reacted (100 equivalents to ACA). The one-pot reaction in the presence of various alcohols (methanol, ethanol, propanol, and butanol) proceeded smoothly to provide the polyacrylamide bearing various urethane moieties with number average molecular weights (
M
n
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| subjects | Acrylamide Butanol Carbonyls Caustic soda Characterization and Evaluation of Materials Chemistry Chemistry and Materials Science Complex Fluids and Microfluidics Crosslinking Ethanol Isocyanates Magnesium Organic Chemistry Original Paper Physical Chemistry Polyacrylamide Polymer Sciences Polymerization Polymers Sodium Soft and Granular Matter Solvents Urethane groups |
| title | Innovation new route for preparation of polyacrylamide bearing urethane group based on one-pot Curtius rearrangement |
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