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Supramolecular polymers from low-melting, easily processable building blocks

Inactive Publication Date: 2010-03-25
SUPRAPOLIX
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0010]The invention relates to 4H-unit containing building blocks with lower melting points than 4H-unit building blocks presently known in the art that dramatically improve the process of making polymeric materials that comprise 4H-units and thereby form supramolecular polymers. Furthermore, the novel supramolecular polymers can also be prepared from the precursors of the 4H-unit building blocks. As the introduced building blocks allow synthetic procedures in the melt at temperatures below 150° C., no (toxic) organic solvents are needed and the relatively low processing temperature makes it possible to perform the chemical functionalisation without the occurrence of side-reactions that would negatively influence the chemical and material properties of the desired material. Especially side reactions of isocyanates that are known to occur at elevated temperatures can be avoided.

Problems solved by technology

However, these polymers are obtained by reaction in chloroform or toluene, both toxic organic solvents, and need prolonged reaction times of several hours in order to reach completion.
However, complex chemistry has to be used to prepare the monomer.
Moreover, the reaction has to be performed in dilute toluene solution, thereby worsening the reaction economy because of the need of removal of large amounts of organic solvent.
Hence, such a synthesis process is commercially less attractive.

Method used

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  • Supramolecular polymers from low-melting, easily processable building blocks
  • Supramolecular polymers from low-melting, easily processable building blocks
  • Supramolecular polymers from low-melting, easily processable building blocks

Examples

Experimental program
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Effect test

example 1

[0073]

[0074]Methyl-4-methyl-3-oxo-valerate (83.0 g) and guanidine carbonate (103.8 g) are heated overnight under a nitrogen atmosphere in ethanol (500 mL) at an oil bath temperature of 80° C. The yellow reaction mixture is evaporated down, ice water is added and the pH is brought to 6 by addition of acetic acid. The white precipitate is filtered, washed with ice water and dried in vacuo. Yield of isocytosine: 61.5 g (70%). 1H NMR (400 MHz, DMSO-d6): δ 10.6 (1H), 6.4 (2H), 5.4 (1H), 2.5 (1H), 1.1 (6H).

example 2

[0075]

[0076]Methyl-4,4-dimethyl-3-oxo-pentanoate (50.0 g) and guanidine carbonate (56.9 g) are heated overnight under a nitrogen atmosphere in ethanol (400 mL) at an oil bath temperature of 80° C. The reaction mixture is filtered, the filtrate is evaporated down, water (50 mL) is added and the pH is brought to 6 by addition of acetic acid. The white precipitate is filtered, washed with several portions of water and dried in vacuo to give a quantitative yield of isocytosine product. 1H NMR (400 MHz, DMSO-d6): δ 10.6 (1H), 6.4 (2H), 5.45 (1H), 1.1 (9H).

example 3

[0077]

[0078]Methyl-propionyl acetate (102.6 g) and guanidine carbonate (142 g) are heated overnight under a nitrogen atmosphere in ethanol (600 mL) at an oil bath temperature of 80° C. The reaction mixture is evaporated down, water is added and the pH is brought to 6 by addition of acetic acid. The white precipitate is filtered, washed with several portions of water and dried in vacuo to give a 90% yield of product. 1H NMR (400 MHz, DMSO-d6): δ 10.6 (1H), 6.4 (2H), 5.4 (1H), 2.3 (2H), 1.1 (3H).

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Abstract

PCT The present invention relates to a supramolecular polymer comprising 1-50 4H-units, said supramolecular polymer being obtainable by reacting at least one monomeric building block with a prepolymer. The present invention further relates to articles or compositions comprising the supramolecular polymer, in particular articles or compositions selected from the group consisting of decorative, thermo-reversible, or self-healing coatings, adhesive compositions, sealing compositions, thickeners, gelators and binders.

Description

FIELD OF THE INVENTION[0001]The invention relates to supramolecular polymers comprising quadruple hydrogen bonding units that are preferably obtained via reaction in the melt. In this reaction, building blocks containing (precursors of) quadruple hydrogen bonding groups are reacted with prepolymers of choice at temperatures below 150° C. The resulting supramolecular polymers show unique new characteristics due to the presence of additional physical interactions between the polymer chains that are based on multiple hydrogen bonding interactions (supramolecular interactions) and benefit from easier and faster preparation using known reactive-processing techniques.BACKGROUND OF THE INVENTION[0002]This invention relates to supramolecular polymers comprising quadruple hydrogen bonding units that are capable of forming at least four H-bridges with each other in a row leading to physical interactions between different polymer chains. The physical interactions originate from multiple hydrog...

Claims

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Application Information

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IPC IPC(8): C09D139/04C08F226/06
CPCC08G18/10C08G18/3212C08G18/3848C08G18/4238C08G18/4277C08G18/73C08G77/388C08G83/008C08G18/7887C08G64/42C08G18/8108
Inventor HOORNE-VAN GEMERT, GABY MARIA LEONARDAJANSSEN, HENRICUS MARIEMEIJER, EGBERT WILLEMBOSMAN, ANTON WILLEM
Owner SUPRAPOLIX
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