Tannin-based non-isocyanate polyurethane adhesives
AssigneeAlbert-Ludwigs-Universität Freiburg
InventorsMarie-Pierre LABORIE, Gopakumar SIVASANKARAPILLAI, Antonio PIZZI
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Abstract
A process for the manufacture of a non-isocyanate polyurethane (NIPU) composition by transesterification of a condensed tannin with a carbonate or a carbonate precursor followed by the reaction with a hardener selected from diamines, triamines, polyamines and mixtures thereof and products and compositions obtained thereby.
Claims14
A process for manufacturing a non-isocyanate polyurethane (NIPU) composition comprising:
- transesterification of a condensed tannin with a carbonate or a carbonate precursor followed by a reaction with a hardener selected from the group consisting of diamines, triamines, polyamines and mixtures thereof, wherein the process comprises:
- a. reacting the condensed tannin with a dialkyl carbonate or a precursor thereof at a temperature in a range from 20 to 40° C. for 1 to 12 h in a solvent selected from the group consisting of water, a C1—to C6 alkanol and a combination thereof in the presence of a catalyst which is a Lewis bases-to obtain a reaction product,
- b. removing the solvent and drying the reaction product at a temperature in the a range of from 30 to 60° C. for 24 to 72 h to obtain a dried reaction product,
- c. mixing the dried reaction product obtained in step b) with a hardener selected from the group consisting of diamines, triamines, polyamines of and mixtures thereof in an amount of 20 to 40 parts by weight of diamine, triamine or polyamine per 100 parts of dried reaction product of b) in an aqueous system at a temperature in the a range from 35 to 70° C.,
- d. adjusting the pH of the system obtained in c) to at least pH 10 to obtain an alkaline reaction medium,
- e. thereafter increasing the temperature to 80 to 110° C. and keeping the alkaline reaction medium at this temperature for 30 to 90 min to obtain a viscous resin, and
- f. cooling the viscous resin obtained in e).
Compositions based on condensed tannins, wherein 30 to 60% of the phenolic hydroxyl groups have been replaced by carbonate groups, or a composition comprising a carbonated condensed tannin, in which 30 to 60% of the phenolic hydroxyl groups are replaced by carbonate groups, and a diamine, triamine or polyamine.
(canceled)
Non-isocyanate polyurethane (NIPU) composition obtainable by reaction of a carbonated derivative of a condensed tannin comprising 30 to 60%, based on the total number of phenolic hydroxyl groups present, of carbonated phenolic hydroxyl groups, with an aliphatic diamine having 2 to 8 carbon atoms in an amount of less than 50 parts by weight of aliphatic diamine per 100 parts of carbonated derivative of tannin.
Dependencies are inferred from the claim text.