Properties of Novel Polyesters Made from Renewable 1,4‐Pentanediol

Novel polyester polyols were prepared in high yields from biobased 1,4‐pentanediol catalyzed by non‐toxic phosphoric acid without using a solvent. These oligomers are terminated with hydroxyl groups and have low residual acid content, making them suitable for use in adhesives by polyurethane formati...

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Veröffentlicht in:	ChemSusChem Jg. 13; H. 3; S. 556 - 563
Hauptverfasser:	Stadler, Bernhard M., Brandt, Adrian, Kux, Alexander, Beck, Horst, Vries, Johannes G.
Format:	Journal Article
Sprache:	Englisch
Veröffentlicht:	Germany Wiley Subscription Services, Inc 07.02.2020 John Wiley and Sons Inc
Schlagworte:	1,4-pentanediol Adhesives Aliphatic compounds Butanediol Chemical industry Hydroxyl groups mechanical properties Melting points Oligomers Phosphoric acid polyester Polyester resins Polyols Polyurethane resins renewable resources Sealants Shape memory Thermodynamic properties renewable resources polyester adhesives 1,4-pentanediol mechanical properties
ISSN:	1864-5631, 1864-564X, 1864-564X
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Abstract	Novel polyester polyols were prepared in high yields from biobased 1,4‐pentanediol catalyzed by non‐toxic phosphoric acid without using a solvent. These oligomers are terminated with hydroxyl groups and have low residual acid content, making them suitable for use in adhesives by polyurethane formation. The thermal behavior of the polyols was studied by differential scanning calorimetry, and tensile testing was performed on the derived polyurethanes. The results were compared with those of polyurethanes obtained with fossil‐based 1,4‐butanediol polyester polyols. Surprisingly, it was found that a crystalline polyester was obtained when aliphatic long‐chain diacids (>C12) were used as the diacid building block. The low melting point of the C12 diacid‐based material allows the development of biobased shape‐memory polymers with very low switching temperatures (<0 °C), an effect that has not yet been reported for a material based on a simple binary polyester. This might find application as thermosensitive adhesives in the packaging of temperature‐sensitive goods such as pharmaceuticals. Furthermore, these results indicate that, although 1,4‐pentanediol cannot be regarded as a direct substitute for 1,4‐butanediol, its novel structure expands the toolbox of the adhesives, coatings, or sealants formulators. Adhesives are going green! 1,4‐Pentanediol obtained through hydrogenation of γ‐valerolactone can be efficiently converted to 100 % biobased polyester polyols. These oligomers provide added value beyond renewability in adhesive and polyurethane applications.
AbstractList	Novel polyester polyols were prepared in high yields from biobased 1,4‐pentanediol catalyzed by non‐toxic phosphoric acid without using a solvent. These oligomers are terminated with hydroxyl groups and have low residual acid content, making them suitable for use in adhesives by polyurethane formation. The thermal behavior of the polyols was studied by differential scanning calorimetry, and tensile testing was performed on the derived polyurethanes. The results were compared with those of polyurethanes obtained with fossil‐based 1,4‐butanediol polyester polyols. Surprisingly, it was found that a crystalline polyester was obtained when aliphatic long‐chain diacids (>C12) were used as the diacid building block. The low melting point of the C12 diacid‐based material allows the development of biobased shape‐memory polymers with very low switching temperatures (<0 °C), an effect that has not yet been reported for a material based on a simple binary polyester. This might find application as thermosensitive adhesives in the packaging of temperature‐sensitive goods such as pharmaceuticals. Furthermore, these results indicate that, although 1,4‐pentanediol cannot be regarded as a direct substitute for 1,4‐butanediol, its novel structure expands the toolbox of the adhesives, coatings, or sealants formulators. Adhesives are going green! 1,4‐Pentanediol obtained through hydrogenation of γ‐valerolactone can be efficiently converted to 100 % biobased polyester polyols. These oligomers provide added value beyond renewability in adhesive and polyurethane applications. Novel polyester polyols were prepared in high yields from biobased 1,4‐pentanediol catalyzed by non‐toxic phosphoric acid without using a solvent. These oligomers are terminated with hydroxyl groups and have low residual acid content, making them suitable for use in adhesives by polyurethane formation. The thermal behavior of the polyols was studied by differential scanning calorimetry, and tensile testing was performed on the derived polyurethanes. The results were compared with those of polyurethanes obtained with fossil‐based 1,4‐butanediol polyester polyols. Surprisingly, it was found that a crystalline polyester was obtained when aliphatic long‐chain diacids (>C12) were used as the diacid building block. The low melting point of the C12 diacid‐based material allows the development of biobased shape‐memory polymers with very low switching temperatures (<0 °C), an effect that has not yet been reported for a material based on a simple binary polyester. This might find application as thermosensitive adhesives in the packaging of temperature‐sensitive goods such as pharmaceuticals. Furthermore, these results indicate that, although 1,4‐pentanediol cannot be regarded as a direct substitute for 1,4‐butanediol, its novel structure expands the toolbox of the adhesives, coatings, or sealants formulators. Novel polyester polyols were prepared in high yields from biobased 1,4‐pentanediol catalyzed by non‐toxic phosphoric acid without using a solvent. These oligomers are terminated with hydroxyl groups and have low residual acid content, making them suitable for use in adhesives by polyurethane formation. The thermal behavior of the polyols was studied by differential scanning calorimetry, and tensile testing was performed on the derived polyurethanes. The results were compared with those of polyurethanes obtained with fossil‐based 1,4‐butanediol polyester polyols. Surprisingly, it was found that a crystalline polyester was obtained when aliphatic long‐chain diacids (>C 12 ) were used as the diacid building block. The low melting point of the C 12 diacid‐based material allows the development of biobased shape‐memory polymers with very low switching temperatures (<0 °C), an effect that has not yet been reported for a material based on a simple binary polyester. This might find application as thermosensitive adhesives in the packaging of temperature‐sensitive goods such as pharmaceuticals. Furthermore, these results indicate that, although 1,4‐pentanediol cannot be regarded as a direct substitute for 1,4‐butanediol, its novel structure expands the toolbox of the adhesives, coatings, or sealants formulators. Novel polyester polyols were prepared in high yields from biobased 1,4-pentanediol catalyzed by non-toxic phosphoric acid without using a solvent. These oligomers are terminated with hydroxyl groups and have low residual acid content, making them suitable for use in adhesives by polyurethane formation. The thermal behavior of the polyols was studied by differential scanning calorimetry, and tensile testing was performed on the derived polyurethanes. The results were compared with those of polyurethanes obtained with fossil-based 1,4-butanediol polyester polyols. Surprisingly, it was found that a crystalline polyester was obtained when aliphatic long-chain diacids (>C12 ) were used as the diacid building block. The low melting point of the C12 diacid-based material allows the development of biobased shape-memory polymers with very low switching temperatures (<0 °C), an effect that has not yet been reported for a material based on a simple binary polyester. This might find application as thermosensitive adhesives in the packaging of temperature-sensitive goods such as pharmaceuticals. Furthermore, these results indicate that, although 1,4-pentanediol cannot be regarded as a direct substitute for 1,4-butanediol, its novel structure expands the toolbox of the adhesives, coatings, or sealants formulators.Novel polyester polyols were prepared in high yields from biobased 1,4-pentanediol catalyzed by non-toxic phosphoric acid without using a solvent. These oligomers are terminated with hydroxyl groups and have low residual acid content, making them suitable for use in adhesives by polyurethane formation. The thermal behavior of the polyols was studied by differential scanning calorimetry, and tensile testing was performed on the derived polyurethanes. The results were compared with those of polyurethanes obtained with fossil-based 1,4-butanediol polyester polyols. Surprisingly, it was found that a crystalline polyester was obtained when aliphatic long-chain diacids (>C12 ) were used as the diacid building block. The low melting point of the C12 diacid-based material allows the development of biobased shape-memory polymers with very low switching temperatures (<0 °C), an effect that has not yet been reported for a material based on a simple binary polyester. This might find application as thermosensitive adhesives in the packaging of temperature-sensitive goods such as pharmaceuticals. Furthermore, these results indicate that, although 1,4-pentanediol cannot be regarded as a direct substitute for 1,4-butanediol, its novel structure expands the toolbox of the adhesives, coatings, or sealants formulators. Novel polyester polyols were prepared in high yields from biobased 1,4-pentanediol catalyzed by non-toxic phosphoric acid without using a solvent. These oligomers are terminated with hydroxyl groups and have low residual acid content, making them suitable for use in adhesives by polyurethane formation. The thermal behavior of the polyols was studied by differential scanning calorimetry, and tensile testing was performed on the derived polyurethanes. The results were compared with those of polyurethanes obtained with fossil-based 1,4-butanediol polyester polyols. Surprisingly, it was found that a crystalline polyester was obtained when aliphatic long-chain diacids (>C ) were used as the diacid building block. The low melting point of the C diacid-based material allows the development of biobased shape-memory polymers with very low switching temperatures (<0 °C), an effect that has not yet been reported for a material based on a simple binary polyester. This might find application as thermosensitive adhesives in the packaging of temperature-sensitive goods such as pharmaceuticals. Furthermore, these results indicate that, although 1,4-pentanediol cannot be regarded as a direct substitute for 1,4-butanediol, its novel structure expands the toolbox of the adhesives, coatings, or sealants formulators.
Author	Beck, Horst Brandt, Adrian Vries, Johannes G. Stadler, Bernhard M. Kux, Alexander
AuthorAffiliation	2 Henkel AG & Co. KGaA Henkel-Str. 67 40589 Düsseldorf Germany 1 Leibniz Institut für Katalyse e. V. an der Universität Rostock Albert-Einstein-Strasse 29a 18055 Rostock Germany
AuthorAffiliation_xml	– name: 2 Henkel AG & Co. KGaA Henkel-Str. 67 40589 Düsseldorf Germany – name: 1 Leibniz Institut für Katalyse e. V. an der Universität Rostock Albert-Einstein-Strasse 29a 18055 Rostock Germany
Author_xml	– sequence: 1 givenname: Bernhard M. orcidid: 0000-0002-6171-6921 surname: Stadler fullname: Stadler, Bernhard M. organization: Universität Rostock – sequence: 2 givenname: Adrian surname: Brandt fullname: Brandt, Adrian email: adrian.brandt@henkel.de organization: Henkel AG & Co. KGaA – sequence: 3 givenname: Alexander surname: Kux fullname: Kux, Alexander organization: Henkel AG & Co. KGaA – sequence: 4 givenname: Horst surname: Beck fullname: Beck, Horst organization: Henkel AG & Co. KGaA – sequence: 5 givenname: Johannes G. orcidid: 0000-0001-5245-7748 surname: Vries fullname: Vries, Johannes G. email: johannes.devries@catalysis.de organization: Universität Rostock
BackLink	https://www.ncbi.nlm.nih.gov/pubmed/31794106$$D View this record in MEDLINE/PubMed
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Keywords	renewable resources polyester adhesives 1,4-pentanediol mechanical properties
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Snippet	Novel polyester polyols were prepared in high yields from biobased 1,4‐pentanediol catalyzed by non‐toxic phosphoric acid without using a solvent. These... Novel polyester polyols were prepared in high yields from biobased 1,4-pentanediol catalyzed by non-toxic phosphoric acid without using a solvent. These...
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SubjectTerms	1,4-pentanediol Adhesives Aliphatic compounds Butanediol Chemical industry Hydroxyl groups mechanical properties Melting points Oligomers Phosphoric acid polyester Polyester resins Polyols Polyurethane resins renewable resources Sealants Shape memory Thermodynamic properties
Title	Properties of Novel Polyesters Made from Renewable 1,4‐Pentanediol
URI	https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fcssc.201902988 https://www.ncbi.nlm.nih.gov/pubmed/31794106 https://www.proquest.com/docview/2351946635 https://www.proquest.com/docview/2320873396 https://pubmed.ncbi.nlm.nih.gov/PMC7027755
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