Diamine chain extenders and method of use

Details Diamine chain extenders and method of use Diamine chain extenders and method of use

1996-05-07

1998-02-17

Gerstl, Robert

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

560 50, C07C20557, C07C22460

Patent

active

057193070

ABSTRACT:
Polyurethane-urea elastomers are made using as a chain extender 2-methyl-1,3-propanediol-bis-p-aminobenzoate which is the reduction product from hydrogenating 2-methyl-1,3-propanediol-bis-p-nitrobenzoate. The latter composition is preferably made by esterifying p-nitrobenzoic acid and 2-methyl-1,3-propanediol using a stoichiometric excess of the diol initially, adequate to render the reaction mixture processible, and after converting to a nonvolatile form sufficient diol to form diester with substantially all of the acid, removing free diol by distillation while continuing the esterification of unreacted acid and transesterification of monoester formed to diester. This process, which can be applied broadly to esterification of other nitroaromatic acids with other aliphatic diols, produces high yields of diester without needing extraneous solvent for processibility and with only water as a by-product. The 2-methyl-1,3-propanediol-bis-p-aminobenzoate exhibits reactivity and processing characteristics which make it a suitable drop-in replacement for MoCA in polyurethane-urea elastomer manufacture.

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Baron, et al. "On the Use of Trimethylene Glycol Di-p-aminobenzoate as a Curing Agent for Polyurethane Elastomers." J Appl. Polym. Sci. 20, pp. 285-286 (1976).
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