Design and Synthesis of Bio-Inspired Polyurethane Films with High Performance
In the present work, the synthesis of segmented polyurethanes functionalized with catechol moieties within the hard or the soft segment is presented. For this purpose, a synthetic route of a new catechol diol was designed. The direct insertion of this catechol-free derivative into the rigid phase le...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2020-11-01
|
| Series: | Polymers |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2073-4360/12/11/2727 |
| _version_ | 1797547648637468672 |
|---|---|
| author | Eva Marina Briz-López Rodrigo Navarro Héctor Martínez-Hernández Lucía Téllez-Jurado Ángel Marcos-Fernández |
| author_facet | Eva Marina Briz-López Rodrigo Navarro Héctor Martínez-Hernández Lucía Téllez-Jurado Ángel Marcos-Fernández |
| author_sort | Eva Marina Briz-López |
| collection | DOAJ |
| description | In the present work, the synthesis of segmented polyurethanes functionalized with catechol moieties within the hard or the soft segment is presented. For this purpose, a synthetic route of a new catechol diol was designed. The direct insertion of this catechol-free derivative into the rigid phase led to segmented polyurethanes with low performance (σ<sub>max</sub> ≈ 4.5 MPa). Nevertheless, when the derivative was formally located within the soft segment, the mechanical properties of the corresponding functionalized polyurethane improved considerably (σ<sub>max</sub> ≈ 16.3 MPa), owing to a significant increase in the degree of polymerization. It is proposed that this difference in reactivity could probably be attributed to a hampering effect of this catecholic ring during the polyaddition reaction. To corroborate this hypothesis, a protection of the aromatic ring was carried out, blocking the hampering effect and avoiding secondary reactions. The polyurethane bearing the protected catechol showed the highest molecular weight and the highest stress at break described to date (σ<sub>max</sub> ≈ 66.1 MPa) for these kind of catechol-functionalized polyurethanes. Therefore, this new approach allows for the obtention of high-performance polyurethane films and can be applied in different sectors, benefiting from the molecular adhesion introduced by the catechol ring. |
| first_indexed | 2024-03-10T14:47:05Z |
| format | Article |
| id | doaj.art-bd28d84194554d5fa57ca556cca0e25d |
| institution | Directory Open Access Journal |
| issn | 2073-4360 |
| language | English |
| last_indexed | 2024-03-10T14:47:05Z |
| publishDate | 2020-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Polymers |
| spelling | doaj.art-bd28d84194554d5fa57ca556cca0e25d2023-11-20T21:17:52ZengMDPI AGPolymers2073-43602020-11-011211272710.3390/polym12112727Design and Synthesis of Bio-Inspired Polyurethane Films with High PerformanceEva Marina Briz-López0Rodrigo Navarro1Héctor Martínez-Hernández2Lucía Téllez-Jurado3Ángel Marcos-Fernández4Instituto Politécnico Nacional-ESIQIE, Dpto. Ing. En Metalurgia y Materiales, UPALM-Zacatenco, 07738 Mexico City, MexicoInstitute of Polymer Science and Technology (ICTP-CSIC), Juan de la Cierva 3, 28006 Madrid, SpainInstituto Politécnico Nacional-ESIQIE, Dpto. Ing. En Metalurgia y Materiales, UPALM-Zacatenco, 07738 Mexico City, MexicoInstituto Politécnico Nacional-ESIQIE, Dpto. Ing. En Metalurgia y Materiales, UPALM-Zacatenco, 07738 Mexico City, MexicoInstitute of Polymer Science and Technology (ICTP-CSIC), Juan de la Cierva 3, 28006 Madrid, SpainIn the present work, the synthesis of segmented polyurethanes functionalized with catechol moieties within the hard or the soft segment is presented. For this purpose, a synthetic route of a new catechol diol was designed. The direct insertion of this catechol-free derivative into the rigid phase led to segmented polyurethanes with low performance (σ<sub>max</sub> ≈ 4.5 MPa). Nevertheless, when the derivative was formally located within the soft segment, the mechanical properties of the corresponding functionalized polyurethane improved considerably (σ<sub>max</sub> ≈ 16.3 MPa), owing to a significant increase in the degree of polymerization. It is proposed that this difference in reactivity could probably be attributed to a hampering effect of this catecholic ring during the polyaddition reaction. To corroborate this hypothesis, a protection of the aromatic ring was carried out, blocking the hampering effect and avoiding secondary reactions. The polyurethane bearing the protected catechol showed the highest molecular weight and the highest stress at break described to date (σ<sub>max</sub> ≈ 66.1 MPa) for these kind of catechol-functionalized polyurethanes. Therefore, this new approach allows for the obtention of high-performance polyurethane films and can be applied in different sectors, benefiting from the molecular adhesion introduced by the catechol ring.https://www.mdpi.com/2073-4360/12/11/2727catechol moietyhigh performance polyurethaneshampering effecthard and soft segmenthigh molecular weight |
| spellingShingle | Eva Marina Briz-López Rodrigo Navarro Héctor Martínez-Hernández Lucía Téllez-Jurado Ángel Marcos-Fernández Design and Synthesis of Bio-Inspired Polyurethane Films with High Performance Polymers catechol moiety high performance polyurethanes hampering effect hard and soft segment high molecular weight |
| title | Design and Synthesis of Bio-Inspired Polyurethane Films with High Performance |
| title_full | Design and Synthesis of Bio-Inspired Polyurethane Films with High Performance |
| title_fullStr | Design and Synthesis of Bio-Inspired Polyurethane Films with High Performance |
| title_full_unstemmed | Design and Synthesis of Bio-Inspired Polyurethane Films with High Performance |
| title_short | Design and Synthesis of Bio-Inspired Polyurethane Films with High Performance |
| title_sort | design and synthesis of bio inspired polyurethane films with high performance |
| topic | catechol moiety high performance polyurethanes hampering effect hard and soft segment high molecular weight |
| url | https://www.mdpi.com/2073-4360/12/11/2727 |
| work_keys_str_mv | AT evamarinabrizlopez designandsynthesisofbioinspiredpolyurethanefilmswithhighperformance AT rodrigonavarro designandsynthesisofbioinspiredpolyurethanefilmswithhighperformance AT hectormartinezhernandez designandsynthesisofbioinspiredpolyurethanefilmswithhighperformance AT luciatellezjurado designandsynthesisofbioinspiredpolyurethanefilmswithhighperformance AT angelmarcosfernandez designandsynthesisofbioinspiredpolyurethanefilmswithhighperformance |