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Biomimetic synthetic rubber and methods for controlling its physical properties through backbone double bond stereochemistry

一种组合物、单体的技术，应用在仿生弹性体组合物领域，能够解决官能团结合至材料、限制等问题

Active Publication Date: 2018-09-07
THE UNIVERSITY OF AKRON +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The design principles required to control the crystallinity and thus the mechanical properties of these materials are generally known, but the inability to incorporate a broad range of functional groups into materials in a controlled manner or to rationally define chain-end functional groups significantly limits these materials and their Application of synthetic analogues of

Method used

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  • Biomimetic synthetic rubber and methods for controlling its physical properties through backbone double bond stereochemistry
  • Biomimetic synthetic rubber and methods for controlling its physical properties through backbone double bond stereochemistry
  • Biomimetic synthetic rubber and methods for controlling its physical properties through backbone double bond stereochemistry

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Experimental program
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Effect test

Embodiment 1

[0151] A. Synthetic steps

[0152] 1. Reagents

[0153] The following chemicals were used as received: acetonitrile (MeCN: Sigma-Aldrich, >99.5%), 1,4-butanediol (Sigma-Aldrich, 99%), chloroform (CHCl 3 : VWR Chemicals, 99%), d-chloroform (CDCl 3 : Apollo, >99%), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU: Sigma-Aldrich, 98%), diethyl ether (Et 2 O: Sigma-Aldrich, ≥99.8%), N,N-dimethylformamide (DMF: Fisher Scientific, LR grade), 2,6-di-tert-butyl-4-methylphenol (BHT: Alfa Aesar, 99%), ethyl acetate (EtOAc: Fisher Scientific, LR grade), hexane (VWR Chemicals, 99%), 1,6-hexanediol (Sigma-Aldrich, 99%), magnesium sulfate (MgSO 4 : Anhydrous, Fisher Scientific, LR grade), 1,3-propanediol (Sigma-Aldrich, 98%), propiolic acid (Acros Organics, 98%), silica gel (SiO 2 : Apollo Scientific, 40-63 microns), Sodium Chloride (NaCl: Fisher Scientific, >99%), Sodium Bicarbonate (NaHCO 3 : Fisher Scientific, >99%), sulfuric acid (Fisher Scientific, >95%), triethylamine (Et 3 N: Fisher S...

Embodiment 2

[0300] Dithiol monomer was obtained from commercial sources and used after purification by distillation. Multifunctional alkyne monomers were obtained by sulfuric acid-catalyzed Fischer esterification of propiolic acid and the corresponding diol in a 2:1 ratio using a Dean-Stark apparatus at 120 °C. At -15 °C, before adding 1 mol% 1,8-diazabicycloundecene (DBU) as a catalyst, by 3 The combination of diyne and dithiol monomers in equimolar ratios undergoes thiol-yne step-growth polymerization. The exothermic reaction was allowed to warm to room temperature and stirred for 1 h, then washed with CHCl 3 After dilution, 2,6-di-tert-butyl-4-methylphenol (BHT, 5%wt) was added to prevent undesired free radical reaction and precipitation into ether. The molar mass of the polymer was varied by varying the amount of dithiol relative to the diyne so that the diyne was always in excess, and by using Et 3 N instead of DBU as catalyst while changing solvent and CHCl 3 and DMF composition...

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Abstract

In various embodiments, the present invention provides a strong, synthetic elastomer materials (and related methods for making same) with mechanical properties that are controlled by the stereochemically-defined double bonds within their backbone, yet have physical properties that are derived from monomer selection and defined, modifiable, chain end groups. The use of the organocatalyzed, stereospecific addition of thiols to activated alkynes, affords isolated high molar mass materials (>100 kDa) via step-growth polymerization with high levels of cis- or trans- double bond content. Furthermore, in various aspects of the present invention, it has been found that changing the monomer composition and chain end groups provides additional control over the materials' physical properties to provide more efficient compounding with polar additives. Using this approach to elastomer synthesis, further end group modification and toughening through various vulcanization strategies are also possible.

Description

[0001] References to related applications [0002] This application claims U.S. Provisional Patent Application Serial No. 62 / 211,367, filed August 28, 2015, entitled "Biomimetic Synthetic Rubber: Control of Physical Properties Through Backbone Double Bond Stereochemistry Through Monomer Selection and End Group Modification," and filed on February 2016 U.S. Provisional Patent Application Serial No. 62 / 295,264, entitled "Biomimetic Synthetic Rubber: Control of Physical Properties Through Backbone Double Bond Stereochemistry Through Monomer Selection and End Group Modification," filed on March 15, all of which are incorporated herein in their entirety for refer to. [0003] Names of parties to the joint research agreement [0004] This application is made pursuant to a joint venture between The University of Akron in Akron, Ohio and The University of Warwick, in Coventry, United Kingdom Research protocol for work done. technical field [0005] One or more embodiments of the in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F2/46
CPCC08F2/46C08F238/00C08F228/02C08G75/045C08F4/6095C08F2500/01C08F2500/04C08F2500/21
Inventor 马修·L·贝克尔安德鲁·P·达夫温赫·X·特鲁昂格克雷格·A·贝尔伊恩·A·巴克尔虞佳祎
Owner THE UNIVERSITY OF AKRON
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