Chemistry of Dimer Acid Production from Fatty Acids and the Structure–Property Relationships of Polyamides Made from These Dimer Acids
While there is abundant literature on using a wide range of biomaterials to make polymers for various adhesive applications, most researchers have generally overlooked developing new adhesives from commercially available bio-based dimerized fatty acids. Some of the literature on the chemistry taking...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-08-01
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| Series: | Polymers |
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| Online Access: | https://www.mdpi.com/2073-4360/15/16/3345 |
| _version_ | 1797583403736891392 |
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| author | Charles R. Frihart |
| author_facet | Charles R. Frihart |
| author_sort | Charles R. Frihart |
| collection | DOAJ |
| description | While there is abundant literature on using a wide range of biomaterials to make polymers for various adhesive applications, most researchers have generally overlooked developing new adhesives from commercially available bio-based dimerized fatty acids. Some of the literature on the chemistry taking place during the clay-catalyzed dimerization of unsaturated fatty acids is generally misleading in that the mechanisms are not consistent with the structures of these dimers and a by-product isostearic acid. A selective acid-catalyzed interlayer model is much more logical than the widely accepted model of clay-catalyzed Diels–Alder reactions. The resulting dimers have a variety of linkages limiting large crystal formation either as oligomeric amides or polyamides. These highly aliphatic fatty acid dimers are used to make a wide range of hot melt polyamide adhesives. The specific structures and amounts of the diacids and diamines and their relative ratios have a big effect on the bio-based polyamide mechanical properties, but analysis of the structure–property relationships has seldom been attempted, since the data are mainly in the patent literature. The diacids derived from plant oils are valuable for making polyamides because of their very high bio-based content and highly tunable properties. |
| first_indexed | 2024-03-10T23:37:24Z |
| format | Article |
| id | doaj.art-3a06ca50c0864d54bf2688c5ec3d3bc6 |
| institution | Directory Open Access Journal |
| issn | 2073-4360 |
| language | English |
| last_indexed | 2024-03-10T23:37:24Z |
| publishDate | 2023-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Polymers |
| spelling | doaj.art-3a06ca50c0864d54bf2688c5ec3d3bc62023-11-19T02:42:46ZengMDPI AGPolymers2073-43602023-08-011516334510.3390/polym15163345Chemistry of Dimer Acid Production from Fatty Acids and the Structure–Property Relationships of Polyamides Made from These Dimer AcidsCharles R. Frihart0Forest Products Laboratory, USDA Forest Service, One Gifford Pinchot Drive, Madison, WI 53726-2398, USAWhile there is abundant literature on using a wide range of biomaterials to make polymers for various adhesive applications, most researchers have generally overlooked developing new adhesives from commercially available bio-based dimerized fatty acids. Some of the literature on the chemistry taking place during the clay-catalyzed dimerization of unsaturated fatty acids is generally misleading in that the mechanisms are not consistent with the structures of these dimers and a by-product isostearic acid. A selective acid-catalyzed interlayer model is much more logical than the widely accepted model of clay-catalyzed Diels–Alder reactions. The resulting dimers have a variety of linkages limiting large crystal formation either as oligomeric amides or polyamides. These highly aliphatic fatty acid dimers are used to make a wide range of hot melt polyamide adhesives. The specific structures and amounts of the diacids and diamines and their relative ratios have a big effect on the bio-based polyamide mechanical properties, but analysis of the structure–property relationships has seldom been attempted, since the data are mainly in the patent literature. The diacids derived from plant oils are valuable for making polyamides because of their very high bio-based content and highly tunable properties.https://www.mdpi.com/2073-4360/15/16/3345fatty acidsdimerizationclay catalystdimer acidisostearic acidpolyamide |
| spellingShingle | Charles R. Frihart Chemistry of Dimer Acid Production from Fatty Acids and the Structure–Property Relationships of Polyamides Made from These Dimer Acids Polymers fatty acids dimerization clay catalyst dimer acid isostearic acid polyamide |
| title | Chemistry of Dimer Acid Production from Fatty Acids and the Structure–Property Relationships of Polyamides Made from These Dimer Acids |
| title_full | Chemistry of Dimer Acid Production from Fatty Acids and the Structure–Property Relationships of Polyamides Made from These Dimer Acids |
| title_fullStr | Chemistry of Dimer Acid Production from Fatty Acids and the Structure–Property Relationships of Polyamides Made from These Dimer Acids |
| title_full_unstemmed | Chemistry of Dimer Acid Production from Fatty Acids and the Structure–Property Relationships of Polyamides Made from These Dimer Acids |
| title_short | Chemistry of Dimer Acid Production from Fatty Acids and the Structure–Property Relationships of Polyamides Made from These Dimer Acids |
| title_sort | chemistry of dimer acid production from fatty acids and the structure property relationships of polyamides made from these dimer acids |
| topic | fatty acids dimerization clay catalyst dimer acid isostearic acid polyamide |
| url | https://www.mdpi.com/2073-4360/15/16/3345 |
| work_keys_str_mv | AT charlesrfrihart chemistryofdimeracidproductionfromfattyacidsandthestructurepropertyrelationshipsofpolyamidesmadefromthesedimeracids |