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Process for preparing aspartates

a technology of aspartate and aspartate, applied in the field of aspartate, can solve the problems of unfinished reaction, shrinking of coating, undesired alcohol formation,

Active Publication Date: 2005-07-21
COVESTRO DEUTSCHLAND AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention relates to novel aspartates that can be used as reactive components in two-component polyurethane coating compositions. These aspartates have improved properties compared to conventional aspartates, including faster curing times, increased hardness, and resistance to hydantoin formation. The invention also provides a process for preparing these aspartates using specific primary amines and maleates or fumarates. The use of these aspartates in coating compositions results in high-quality coatings that are resistant to solvents, weather, and abrasion.

Problems solved by technology

It has been found, however, that this reaction does not proceed to completion during the course of the actual synthesis process (e.g., 24 hours with stirring at 60° C.).
This hydantoin formation might lead to a shrinking of the coating and undesired alcohol formation.

Method used

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  • Process for preparing aspartates
  • Process for preparing aspartates
  • Process for preparing aspartates

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0062] A round bottom flask was fitted with stirrer, heating mantle, nitrogen inlet, thermocouple and addition funnel. 58 parts (1.0 eq.) of 2-metyl-1,5-pentandiamine was added to the flask at room temperature. 137.7 parts (0.8 eq.) of diethyl maleate was added through the addition funnel over a period of sixty minutes. The temperature of the flask rose to 35° C. The reaction was heated to 60° C. and held for seven hours at which time an iodometric titration showed that the reaction was complete. The reaction mixture was cooled to room temperature. 25.02 parts (0.2 eq.) of N-ethylmaleimide was added. The temperature was held at 25° C. for eight hours until the reaction was complete. The clear, nearly colorless final product had a viscosity of 260 cps and an amine number of 251 (theoretical amine number: 253).

example 2

[0063] A round bottom flask was fitted with stirrer, heating mantle, nitrogen inlet, thermocouple and addition funnel. 105 parts (1.0 eq.) of bis-(paraaminocyclohexyl)methane was added to the flask at room temperature. 129 parts (0.75 eq.) of diethyl maleate was added through the addition funnel over a period of sixty minutes. The temperature of the flask rose to 33° C. The reaction was heated to 60° C. and held for ten hours at which time an iodometric titration showed that the reaction was complete. The reaction mixture was cooled to room temperature. 31.28 parts (0.25 eq.) of N-ethylmaleimide was added. The temperature was held at 25° C. for eight hours, after which time the reaction was complete. The clear, nearly colorless final product had a viscosity of 6300 cps and an amine number of 209 (theoretical amine number: 211).

example 3

[0064] A round bottom flask was fitted with stirrer, heating mantle, nitrogen inlet, thermocouple and addition funnel. 85 parts (1.0 eq.) of 5-amino-1,3,3-trimethylcyclohexanemethylamine (“isophorone diamine”) was added to the flask at room temperature. 137.7 parts (0.80 eq.) of diethyl maleate was added through the addition funnel over a period of sixty minutes. The temperature of the flask rose to 35° C. The reaction was heated to 60° C. and held for ten hours at which time an iodometric titration showed that the reaction was complete. The reaction mixture was cooled to room temperature. 25.1 parts (0.20 eq.) of N-ethylmaleimide was added. The temperature was held at 25° C. for eight hours, after which time the reaction was complete. The clear, nearly colorless final product had a viscosity of: 2070 cps and an amine number of 223 (theoretical amine number: 227).

[0065] The samples from the Examples were hand mixed with Desmodur N-3300 (a trimerized hexane diisocyanate having an NC...

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Abstract

The present invention relates to novel aspartates, their method of production and the use of these aspartates as reactive components for polyisocyanates in two-component polyurethane coating compositions and for preparing polyurethane prepolymers. The aspartates are prepared by first reacting a di- or polyamine with an unsaturated ester and then reacting the resultant product with a maleimide.

Description

BACKGROUND OF THE INVENTION [0001] The present invention relates to novel aspartates, a process for preparing them from primary amines and maleates and to their use as reactive components for polyisocyanates in two-component polyurethane coating compositions and for preparing polyurethane prepolymers. [0002] Two-component coating compositions which contain, as binder, a polyisocyanate component combined with one or more isocyanate-reactive components are known. They are suitable for preparing high quality coatings which are hard, elastic, abrasion resistant, solvent resistant and weather resistant. [0003] Secondary polyamines which contain ester groups have become established in the two-component surface coating industry. They are particularly suitable, in combination with lacquer polyisocyanates, as binders in low-solvent or solvent-free, high solids coating compositions because they provide rapid curing of the coatings at low temperatures. [0004] These secondary polyamines are pol...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07D207/40C07D207/416C08G18/00C08G18/38C08G18/79C09D175/04
CPCC07D207/416C09D175/04C08G18/792C08G18/3821C08G18/00
Inventor DANIELMEIER, KARSTENGAMBINO, CHARLES A.GERTZMANN, ROLFROESLER, RICHARD R.WAYT, TERRELL D.VARGO, MICHELE E.SQUILLER, EDWARD P.HENDERSON, KAREN M.
Owner COVESTRO DEUTSCHLAND AG