Triblock polyester thermoplastic elastomers with semi-aromatic polymer end blocks by ring-opening copolymerization
Thermoplastic elastomers benefit from high elasticity and straightforward (re)processability; they are widely used across a multitude of sectors. Currently, the majority derive from oil, do not degrade or undergo chemical recycling. Here a new series of ABA triblock polyesters are synthesized and sh...
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| Published in | Chemical science (Cambridge) Vol. 11; no. 25; pp. 6567 - 6581 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
England
Royal Society of Chemistry
04.05.2020
The Royal Society of Chemistry |
| Subjects | |
| Online Access | Get full text |
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| Abstract | Thermoplastic elastomers benefit from high elasticity and straightforward (re)processability; they are widely used across a multitude of sectors. Currently, the majority derive from oil, do not degrade or undergo chemical recycling. Here a new series of ABA triblock polyesters are synthesized and show high-performances as degradable thermoplastic elastomers; their composition is poly(cyclohexene-
alt
-phthalate)-
b
-poly( -decalactone)-
b
-poly(cyclohexene-
alt
-phthalate) {PE-PDL-PE}. The synthesis is accomplished using a zinc(
ii
)/magnesium(
ii
) catalyst, in a one-pot procedure where -decalactone ring-opening polymerization yielding dihydroxyl telechelic poly( -decalatone) (PDL, soft-block) occurs first and, then, addition of phthalic anhydride/cyclohexene oxide ring-opening copolymerization delivers semi-aromatic polyester (PE, hard-block) end-blocks. The block compositions are straightforward to control, from the initial monomer stoichiometry, and conversions are high (85-98%). Two series of polyesters are prepared: (1) TBPE-1 to TBPE-5 feature an equivalent hard-block volume fraction (
f
hard
= 0.4) and variable molar masses 40-100 kg mol
−1
; (2) TBPE-5 to TBPE-9 feature equivalent molar masses (∼100 kg mol
−1
) and variable hard-block volume fractions (0.12 <
f
hard
< 0.4). Polymers are characterized using spectroscopies, size-exclusion chromatography (SEC), thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC) and dynamic mechanical thermal analysis (DMTA). They are amorphous, with two glass transition temperatures (∼−51 °C for PDL; +138 °C for PE), and block phase separation is confirmed using small angle X-ray scattering (SAXS). Tensile mechanical performances reveal thermoplastic elastomers (
f
hard
< 0.4 and
N
> 1300) with linear stress-strain relationships, high ultimate tensile strengths (
σ
b
= 1-5 MPa), very high elongations at break (
b
= 1000-1900%) and excellent elastic recoveries (98%). There is a wide operating temperature range (−51 to +138 °C), an operable processing temperature range (+100 to +200 °C) and excellent thermal stability (
T
d,5%
∼ 300 °C). The polymers are stable in aqueous environments, at room temperature, but are hydrolyzed upon gentle heating (60 °C) and treatment with an organic acid (
para
-toluene sulfonic acid) or a common lipase (Novozyme® 51032). The new block polyesters show significant potential as sustainable thermoplastic elastomers with better properties than well-known styrenic block copolymers or polylactide-derived elastomers. The straightforward synthesis allows for other commercially available and/or bio-derived lactones, epoxides and anhydrides to be developed in the future.
A new series of block polyester thermoplastic elastomers are prepared by a one-pot procedure; they show properties competitive or better than conventional materials and can be fully degraded after use. |
|---|---|
| AbstractList | Thermoplastic elastomers benefit from high elasticity and straightforward (re)processability; they are widely used across a multitude of sectors. Currently, the majority derive from oil, do not degrade or undergo chemical recycling. Here a new series of ABA triblock polyesters are synthesized and show high-performances as degradable thermoplastic elastomers; their composition is poly(cyclohexene-alt-phthalate)-b-poly(ε-decalactone)-b-poly(cyclohexene-alt-phthalate) {PE-PDL-PE}. The synthesis is accomplished using a zinc(ii)/magnesium(ii) catalyst, in a one-pot procedure where ε-decalactone ring-opening polymerization yielding dihydroxyl telechelic poly(ε-decalatone) (PDL, soft-block) occurs first and, then, addition of phthalic anhydride/cyclohexene oxide ring-opening copolymerization delivers semi-aromatic polyester (PE, hard-block) end-blocks. The block compositions are straightforward to control, from the initial monomer stoichiometry, and conversions are high (85-98%). Two series of polyesters are prepared: (1) TBPE-1 to TBPE-5 feature an equivalent hard-block volume fraction (f hard = 0.4) and variable molar masses 40-100 kg mol-1; (2) TBPE-5 to TBPE-9 feature equivalent molar masses (∼100 kg mol-1) and variable hard-block volume fractions (0.12 < f hard < 0.4). Polymers are characterized using spectroscopies, size-exclusion chromatography (SEC), thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC) and dynamic mechanical thermal analysis (DMTA). They are amorphous, with two glass transition temperatures (∼-51 °C for PDL; +138 °C for PE), and block phase separation is confirmed using small angle X-ray scattering (SAXS). Tensile mechanical performances reveal thermoplastic elastomers (f hard < 0.4 and N > 1300) with linear stress-strain relationships, high ultimate tensile strengths (σ b = 1-5 MPa), very high elongations at break (ε b = 1000-1900%) and excellent elastic recoveries (98%). There is a wide operating temperature range (-51 to +138 °C), an operable processing temperature range (+100 to +200 °C) and excellent thermal stability (T d,5% ∼ 300 °C). The polymers are stable in aqueous environments, at room temperature, but are hydrolyzed upon gentle heating (60 °C) and treatment with an organic acid (para-toluene sulfonic acid) or a common lipase (Novozyme® 51032). The new block polyesters show significant potential as sustainable thermoplastic elastomers with better properties than well-known styrenic block copolymers or polylactide-derived elastomers. The straightforward synthesis allows for other commercially available and/or bio-derived lactones, epoxides and anhydrides to be developed in the future.Thermoplastic elastomers benefit from high elasticity and straightforward (re)processability; they are widely used across a multitude of sectors. Currently, the majority derive from oil, do not degrade or undergo chemical recycling. Here a new series of ABA triblock polyesters are synthesized and show high-performances as degradable thermoplastic elastomers; their composition is poly(cyclohexene-alt-phthalate)-b-poly(ε-decalactone)-b-poly(cyclohexene-alt-phthalate) {PE-PDL-PE}. The synthesis is accomplished using a zinc(ii)/magnesium(ii) catalyst, in a one-pot procedure where ε-decalactone ring-opening polymerization yielding dihydroxyl telechelic poly(ε-decalatone) (PDL, soft-block) occurs first and, then, addition of phthalic anhydride/cyclohexene oxide ring-opening copolymerization delivers semi-aromatic polyester (PE, hard-block) end-blocks. The block compositions are straightforward to control, from the initial monomer stoichiometry, and conversions are high (85-98%). Two series of polyesters are prepared: (1) TBPE-1 to TBPE-5 feature an equivalent hard-block volume fraction (f hard = 0.4) and variable molar masses 40-100 kg mol-1; (2) TBPE-5 to TBPE-9 feature equivalent molar masses (∼100 kg mol-1) and variable hard-block volume fractions (0.12 < f hard < 0.4). Polymers are characterized using spectroscopies, size-exclusion chromatography (SEC), thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC) and dynamic mechanical thermal analysis (DMTA). They are amorphous, with two glass transition temperatures (∼-51 °C for PDL; +138 °C for PE), and block phase separation is confirmed using small angle X-ray scattering (SAXS). Tensile mechanical performances reveal thermoplastic elastomers (f hard < 0.4 and N > 1300) with linear stress-strain relationships, high ultimate tensile strengths (σ b = 1-5 MPa), very high elongations at break (ε b = 1000-1900%) and excellent elastic recoveries (98%). There is a wide operating temperature range (-51 to +138 °C), an operable processing temperature range (+100 to +200 °C) and excellent thermal stability (T d,5% ∼ 300 °C). The polymers are stable in aqueous environments, at room temperature, but are hydrolyzed upon gentle heating (60 °C) and treatment with an organic acid (para-toluene sulfonic acid) or a common lipase (Novozyme® 51032). The new block polyesters show significant potential as sustainable thermoplastic elastomers with better properties than well-known styrenic block copolymers or polylactide-derived elastomers. The straightforward synthesis allows for other commercially available and/or bio-derived lactones, epoxides and anhydrides to be developed in the future. Thermoplastic elastomers benefit from high elasticity and straightforward (re)processability; they are widely used across a multitude of sectors. Currently, the majority derive from oil, do not degrade or undergo chemical recycling. Here a new series of ABA triblock polyesters are synthesized and show high-performances as degradable thermoplastic elastomers; their composition is poly(cyclohexene- alt -phthalate)- b -poly( -decalactone)- b -poly(cyclohexene- alt -phthalate) {PE-PDL-PE}. The synthesis is accomplished using a zinc( ii )/magnesium( ii ) catalyst, in a one-pot procedure where -decalactone ring-opening polymerization yielding dihydroxyl telechelic poly( -decalatone) (PDL, soft-block) occurs first and, then, addition of phthalic anhydride/cyclohexene oxide ring-opening copolymerization delivers semi-aromatic polyester (PE, hard-block) end-blocks. The block compositions are straightforward to control, from the initial monomer stoichiometry, and conversions are high (85-98%). Two series of polyesters are prepared: (1) TBPE-1 to TBPE-5 feature an equivalent hard-block volume fraction ( f hard = 0.4) and variable molar masses 40-100 kg mol −1 ; (2) TBPE-5 to TBPE-9 feature equivalent molar masses (∼100 kg mol −1 ) and variable hard-block volume fractions (0.12 < f hard < 0.4). Polymers are characterized using spectroscopies, size-exclusion chromatography (SEC), thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC) and dynamic mechanical thermal analysis (DMTA). They are amorphous, with two glass transition temperatures (∼−51 °C for PDL; +138 °C for PE), and block phase separation is confirmed using small angle X-ray scattering (SAXS). Tensile mechanical performances reveal thermoplastic elastomers ( f hard < 0.4 and N > 1300) with linear stress-strain relationships, high ultimate tensile strengths ( σ b = 1-5 MPa), very high elongations at break ( b = 1000-1900%) and excellent elastic recoveries (98%). There is a wide operating temperature range (−51 to +138 °C), an operable processing temperature range (+100 to +200 °C) and excellent thermal stability ( T d,5% ∼ 300 °C). The polymers are stable in aqueous environments, at room temperature, but are hydrolyzed upon gentle heating (60 °C) and treatment with an organic acid ( para -toluene sulfonic acid) or a common lipase (Novozyme® 51032). The new block polyesters show significant potential as sustainable thermoplastic elastomers with better properties than well-known styrenic block copolymers or polylactide-derived elastomers. The straightforward synthesis allows for other commercially available and/or bio-derived lactones, epoxides and anhydrides to be developed in the future. A new series of block polyester thermoplastic elastomers are prepared by a one-pot procedure; they show properties competitive or better than conventional materials and can be fully degraded after use. Thermoplastic elastomers benefit from high elasticity and straightforward (re)processability; they are widely used across a multitude of sectors. Currently, the majority derive from oil, do not degrade or undergo chemical recycling. Here a new series of ABA triblock polyesters are synthesized and show high-performances as degradable thermoplastic elastomers; their composition is poly(cyclohexene- -phthalate)- -poly(ε-decalactone)- -poly(cyclohexene- -phthalate) {PE-PDL-PE}. The synthesis is accomplished using a zinc(ii)/magnesium(ii) catalyst, in a one-pot procedure where ε-decalactone ring-opening polymerization yielding dihydroxyl telechelic poly(ε-decalatone) (PDL, soft-block) occurs first and, then, addition of phthalic anhydride/cyclohexene oxide ring-opening copolymerization delivers semi-aromatic polyester (PE, hard-block) end-blocks. The block compositions are straightforward to control, from the initial monomer stoichiometry, and conversions are high (85-98%). Two series of polyesters are prepared: (1) TBPE-1 to TBPE-5 feature an equivalent hard-block volume fraction ( = 0.4) and variable molar masses 40-100 kg mol ; (2) TBPE-5 to TBPE-9 feature equivalent molar masses (∼100 kg mol ) and variable hard-block volume fractions (0.12 < < 0.4). Polymers are characterized using spectroscopies, size-exclusion chromatography (SEC), thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC) and dynamic mechanical thermal analysis (DMTA). They are amorphous, with two glass transition temperatures (∼-51 °C for PDL; +138 °C for PE), and block phase separation is confirmed using small angle X-ray scattering (SAXS). Tensile mechanical performances reveal thermoplastic elastomers ( < 0.4 and > 1300) with linear stress-strain relationships, high ultimate tensile strengths ( = 1-5 MPa), very high elongations at break ( = 1000-1900%) and excellent elastic recoveries (98%). There is a wide operating temperature range (-51 to +138 °C), an operable processing temperature range (+100 to +200 °C) and excellent thermal stability ( ∼ 300 °C). The polymers are stable in aqueous environments, at room temperature, but are hydrolyzed upon gentle heating (60 °C) and treatment with an organic acid ( -toluene sulfonic acid) or a common lipase (Novozyme® 51032). The new block polyesters show significant potential as sustainable thermoplastic elastomers with better properties than well-known styrenic block copolymers or polylactide-derived elastomers. The straightforward synthesis allows for other commercially available and/or bio-derived lactones, epoxides and anhydrides to be developed in the future. Thermoplastic elastomers benefit from high elasticity and straightforward (re)processability; they are widely used across a multitude of sectors. Currently, the majority derive from oil, do not degrade or undergo chemical recycling. Here a new series of ABA triblock polyesters are synthesized and show high-performances as degradable thermoplastic elastomers; their composition is poly(cyclohexene- alt -phthalate)- b -poly(ε-decalactone)- b -poly(cyclohexene- alt -phthalate) {PE–PDL–PE}. The synthesis is accomplished using a zinc( ii )/magnesium( ii ) catalyst, in a one-pot procedure where ε-decalactone ring-opening polymerization yielding dihydroxyl telechelic poly(ε-decalatone) (PDL, soft-block) occurs first and, then, addition of phthalic anhydride/cyclohexene oxide ring-opening copolymerization delivers semi-aromatic polyester (PE, hard-block) end-blocks. The block compositions are straightforward to control, from the initial monomer stoichiometry, and conversions are high (85–98%). Two series of polyesters are prepared: (1) TBPE-1 to TBPE-5 feature an equivalent hard-block volume fraction ( f hard = 0.4) and variable molar masses 40–100 kg mol −1 ; (2) TBPE-5 to TBPE-9 feature equivalent molar masses (∼100 kg mol −1 ) and variable hard-block volume fractions (0.12 < f hard < 0.4). Polymers are characterized using spectroscopies, size-exclusion chromatography (SEC), thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC) and dynamic mechanical thermal analysis (DMTA). They are amorphous, with two glass transition temperatures (∼−51 °C for PDL; +138 °C for PE), and block phase separation is confirmed using small angle X-ray scattering (SAXS). Tensile mechanical performances reveal thermoplastic elastomers ( f hard < 0.4 and N > 1300) with linear stress–strain relationships, high ultimate tensile strengths ( σ b = 1–5 MPa), very high elongations at break ( ε b = 1000–1900%) and excellent elastic recoveries (98%). There is a wide operating temperature range (−51 to +138 °C), an operable processing temperature range (+100 to +200 °C) and excellent thermal stability ( T d,5% ∼ 300 °C). The polymers are stable in aqueous environments, at room temperature, but are hydrolyzed upon gentle heating (60 °C) and treatment with an organic acid ( para -toluene sulfonic acid) or a common lipase (Novozyme® 51032). The new block polyesters show significant potential as sustainable thermoplastic elastomers with better properties than well-known styrenic block copolymers or polylactide-derived elastomers. The straightforward synthesis allows for other commercially available and/or bio-derived lactones, epoxides and anhydrides to be developed in the future. Thermoplastic elastomers benefit from high elasticity and straightforward (re)processability; they are widely used across a multitude of sectors. Currently, the majority derive from oil, do not degrade or undergo chemical recycling. Here a new series of ABA triblock polyesters are synthesized and show high-performances as degradable thermoplastic elastomers; their composition is poly(cyclohexene-alt-phthalate)-b-poly(ϵ-decalactone)-b-poly(cyclohexene-alt-phthalate) {PE–PDL–PE}. The synthesis is accomplished using a zinc(ii)/magnesium(ii) catalyst, in a one-pot procedure where ϵ-decalactone ring-opening polymerization yielding dihydroxyl telechelic poly(ϵ-decalatone) (PDL, soft-block) occurs first and, then, addition of phthalic anhydride/cyclohexene oxide ring-opening copolymerization delivers semi-aromatic polyester (PE, hard-block) end-blocks. The block compositions are straightforward to control, from the initial monomer stoichiometry, and conversions are high (85–98%). Two series of polyesters are prepared: (1) TBPE-1 to TBPE-5 feature an equivalent hard-block volume fraction (fhard = 0.4) and variable molar masses 40–100 kg mol−1; (2) TBPE-5 to TBPE-9 feature equivalent molar masses (∼100 kg mol−1) and variable hard-block volume fractions (0.12 < fhard < 0.4). Polymers are characterized using spectroscopies, size-exclusion chromatography (SEC), thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC) and dynamic mechanical thermal analysis (DMTA). They are amorphous, with two glass transition temperatures (∼−51 °C for PDL; +138 °C for PE), and block phase separation is confirmed using small angle X-ray scattering (SAXS). Tensile mechanical performances reveal thermoplastic elastomers (fhard < 0.4 and N > 1300) with linear stress–strain relationships, high ultimate tensile strengths (σb = 1–5 MPa), very high elongations at break (ϵb = 1000–1900%) and excellent elastic recoveries (98%). There is a wide operating temperature range (−51 to +138 °C), an operable processing temperature range (+100 to +200 °C) and excellent thermal stability (Td,5% ∼ 300 °C). The polymers are stable in aqueous environments, at room temperature, but are hydrolyzed upon gentle heating (60 °C) and treatment with an organic acid (para-toluene sulfonic acid) or a common lipase (Novozyme® 51032). The new block polyesters show significant potential as sustainable thermoplastic elastomers with better properties than well-known styrenic block copolymers or polylactide-derived elastomers. The straightforward synthesis allows for other commercially available and/or bio-derived lactones, epoxides and anhydrides to be developed in the future. Thermoplastic elastomers benefit from high elasticity and straightforward (re)processability; they are widely used across a multitude of sectors. Currently, the majority derive from oil, do not degrade or undergo chemical recycling. Here a new series of ABA triblock polyesters are synthesized and show high-performances as degradable thermoplastic elastomers; their composition is poly(cyclohexene- alt -phthalate)- b -poly(ε-decalactone)- b -poly(cyclohexene- alt -phthalate) {PE–PDL–PE}. The synthesis is accomplished using a zinc( ii )/magnesium( ii ) catalyst, in a one-pot procedure where ε-decalactone ring-opening polymerization yielding dihydroxyl telechelic poly(ε-decalatone) (PDL, soft-block) occurs first and, then, addition of phthalic anhydride/cyclohexene oxide ring-opening copolymerization delivers semi-aromatic polyester (PE, hard-block) end-blocks. The block compositions are straightforward to control, from the initial monomer stoichiometry, and conversions are high (85–98%). Two series of polyesters are prepared: (1) TBPE-1 to TBPE-5 feature an equivalent hard-block volume fraction ( f hard = 0.4) and variable molar masses 40–100 kg mol −1 ; (2) TBPE-5 to TBPE-9 feature equivalent molar masses (∼100 kg mol −1 ) and variable hard-block volume fractions (0.12 < f hard < 0.4). Polymers are characterized using spectroscopies, size-exclusion chromatography (SEC), thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC) and dynamic mechanical thermal analysis (DMTA). They are amorphous, with two glass transition temperatures (∼−51 °C for PDL; +138 °C for PE), and block phase separation is confirmed using small angle X-ray scattering (SAXS). Tensile mechanical performances reveal thermoplastic elastomers ( f hard < 0.4 and N > 1300) with linear stress–strain relationships, high ultimate tensile strengths ( σ b = 1–5 MPa), very high elongations at break ( ε b = 1000–1900%) and excellent elastic recoveries (98%). There is a wide operating temperature range (−51 to +138 °C), an operable processing temperature range (+100 to +200 °C) and excellent thermal stability ( T d,5% ∼ 300 °C). The polymers are stable in aqueous environments, at room temperature, but are hydrolyzed upon gentle heating (60 °C) and treatment with an organic acid ( para -toluene sulfonic acid) or a common lipase (Novozyme® 51032). The new block polyesters show significant potential as sustainable thermoplastic elastomers with better properties than well-known styrenic block copolymers or polylactide-derived elastomers. The straightforward synthesis allows for other commercially available and/or bio-derived lactones, epoxides and anhydrides to be developed in the future. A new series of block polyester thermoplastic elastomers are prepared by a one-pot procedure; they show properties competitive or better than conventional materials and can be fully degraded after use. |
| Author | Carrodeguas, Leticia Peña Lee, Koon-Yang Chen, Thomas T. D Terrill, Nicholas J Williams, Charlotte K Gregory, Georgina L Sulley, Gregory S Santmarti, Alba |
| AuthorAffiliation | Harwell Science and Innovation Campus Oxford Chemistry Imperial College London Chemistry Research Laboratory Diamond Light Source Department of Aeronautical Engineering |
| AuthorAffiliation_xml | – name: Chemistry Research Laboratory – name: Department of Aeronautical Engineering – name: Oxford Chemistry – name: Harwell Science and Innovation Campus – name: Imperial College London – name: Diamond Light Source |
| Author_xml | – sequence: 1 givenname: Georgina L surname: Gregory fullname: Gregory, Georgina L – sequence: 2 givenname: Gregory S surname: Sulley fullname: Sulley, Gregory S – sequence: 3 givenname: Leticia Peña surname: Carrodeguas fullname: Carrodeguas, Leticia Peña – sequence: 4 givenname: Thomas T. D surname: Chen fullname: Chen, Thomas T. D – sequence: 5 givenname: Alba surname: Santmarti fullname: Santmarti, Alba – sequence: 6 givenname: Nicholas J surname: Terrill fullname: Terrill, Nicholas J – sequence: 7 givenname: Koon-Yang surname: Lee fullname: Lee, Koon-Yang – sequence: 8 givenname: Charlotte K surname: Williams fullname: Williams, Charlotte K |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/34094122$$D View this record in MEDLINE/PubMed |
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| Snippet | Thermoplastic elastomers benefit from high elasticity and straightforward (re)processability; they are widely used across a multitude of sectors. Currently,... |
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| SubjectTerms | Aqueous environments Block copolymers Chemistry Copolymerization Cyclohexene Decalactone Differential scanning calorimetry Elastic recovery Equivalence Glass transition temperature Gravimetric analysis Lactones Lipase Magnesium Operating temperature Phase separation Phthalates Phthalic anhydride Polyester resins Polyester thermoplastic elastomers Ring opening polymerization Room temperature Stoichiometry Stress-strain relationships Temperature Thermal stability X-ray scattering |
| Title | Triblock polyester thermoplastic elastomers with semi-aromatic polymer end blocks by ring-opening copolymerization |
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