Polyaspartic acid ester compositions which contain polyaspartic acid esters with primary amino groups and small amounts of fumaric acid dialkyl esters

Patent metadata

Field	Value
Publication number	US-11230522-B2
Application number	US-201816648344-A
Country	US
Kind code	B2
Filing date	Sep 14, 2018
Priority date	Sep 19, 2017
Publication date	Jan 25, 2022
Grant date	Jan 25, 2022

Abstract

The present invention relates to polyaspartic acid ester compositions which contain polyaspartic acid esters with primary amino groups and small amounts of fumaric acid dialkyl esters, to a method for preparing same and the use thereof as a reactive component for polyisocyanates in two-component polyurethane systems.

First claim

The invention claimed is:

1. A polyaspartic ester composition comprising one or more polyaspartic esters of the general formula (I)

in which
X is an m-valent organic radical, optionally containing one or more heteroatoms obtained by removing the primary amino groups from a corresponding polyamine that has (cyclo)aliphatically or araliphatically attached amino groups and is in the molecular weight range from 60 to 6000 g/mol, and which comprises further functional groups that are reactive toward isocyanate groups and/or inert at temperatures of up to 100° C.,
R1 and R2 are identical or different organic radicals each having 1 to 18 carbon atoms,
m is an integer >1,
and
one or more polyaspartic esters having a primary amino group that are of the general formula (II)

in which
n is m−1,
X and radicals R1 and R2 have the meanings defined for the polyaspartic esters of the general formula (I),
wherein a proportion of the polyaspartic esters of the general formula (II) corresponds to from 4% to 15% of a total GC surface area of the composition measured by gas chromatogram as area-%, wherein the total GC surface area is a sum of the individual surface areas of the polyaspartic esters of the general formulas (I) and (II) and is equal to 100%, and wherein the composition comprises dialkyl fumarate in a proportion of 0.01 to 1% by weight.

2. A process for producing the polyaspartic ester composition of claim 1 comprising: combining one or more polyaspartic esters of the general formula (I)

in which
X is an m-valent organic radical, optionally containing one or more heteroatoms obtained by removing the primary amino groups from a corresponding polyamine that has (cyclo)aliphatically or araliphatically attached amino groups and is in the molecular weight range from 60 to 6000 g/mol, and which comprises further functional groups that are reactive toward isocyanate groups and/or inert at temperatures of up to 100° C.,
R1 and R2 are identical or different organic radicals, preferably identical or different alkyl radicals each having 1 to 18 carbon atoms,
m is an integer >1,
with
one or more polyaspartic esters having a primary amino group that are of the general formula (II)

in which
n is m−1,
X and radicals R1 and R2 have the meanings defined for the polyaspartic esters of the general formula (I),
produced by reacting polyamines of the general formula (III),

in which X and m have the meaning defined for the polyaspartic esters of the general formula (I),
with compounds of the general formula (IV)
R1OOC—CH═CH—COOR2  (IV),

in which the radicals R1 and R2 have the meaning defined for the polyaspartic esters of the general formula (I);
and removing an unreacted proportion of the compound of the general formula (IV) by distillation,
wherein the polyaspartic ester composition comprises a proportion of the polyaspartic ester of the general formula (II) of 4% to 15% of a total GC surface area measured by gas chromatogram as area-%, wherein the total GC surface area is a sum of the individual surface areas of the polyaspartic esters of the general formulas (I) and (II) and is equal to 100%, and wherein the composition comprises dialkyl fumarate in a proportion of 0.01 to 1% by weight.

3. A two-component polyurethane system, comprising the polyaspartic ester composition of claim 1 and a reactive component that is reactive towards the polyaspartic ester composition of claim 1 .

4. A substrate coated with a polyaspartic ester composition as claimed in claim 1 .

5. A prepolymer, comprising a reaction product of the polyaspartic ester composition of claim 1 with a reactive component that is reactive towards the polyaspartic ester composition of claim 1 .

6. The polyaspartic ester composition of claim 1 , wherein the composition has a platinum-cobalt color index of 5≤25.

Assignees

• Covestro Deutschland Ag

Inventors

• Greszta-Franz Dorota
• Weikard Jan
• Wintermantel Matthias
• Maleika Robert
• Klimmasch Thomas
• Schuettler Thomas

Classifications

• C08G18/3821 Primary

  Carboxylic acids; Esters thereof with monohydroxyl compounds · CPC title

• C09D175/04

  Polyurethanes · CPC title

• C07C229/24 Primary

  having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid · CPC title

• C08G18/792 Primary

  formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates · CPC title

• C07C229/26

  having more than one amino group bound to the carbon skeleton, e.g. lysine · CPC title