Polyaspartic acid ester compositions and method for purification

Patent metadata

Field	Value
Publication number	US-10968165-B2
Application number	US-201816648366-A
Country	US
Kind code	B2
Filing date	Sep 14, 2018
Priority date	Sep 19, 2017
Publication date	Apr 6, 2021
Grant date	Apr 6, 2021

Abstract

The present invention relates to a method for purifying polyaspartic acid ester compositions and to the provision of polyaspartic acid ester compositions that contain 0.01 to <2% by weight fumaric acid dialkyl esters.

First claim

The invention claimed is:

1. A polyaspartic ester composition, comprising: a compound of the general formula (I)

in which
X is an m-valent organic radical obtained by removing primary amino groups from a corresponding polyamine 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., wherein the m-valent organic radical optionally contains one or more heteroatoms, and wherein the corresponding polyamine comprises aromatically, (cyclo)aliphatically, or araliphatically attached primary amino groups,
R1 and R2 are identical or different organic radicals each having 1 to 18 carbon atoms,
m is an integer >1

wherein the polyaspartic ester composition comprises from 0.01% to <2% by weight of dialkyl fumarate and has a platinum-cobalt color index of <100.

2. A process for purifying a polyaspartic ester composition comprising: forming a polyaspartic ester of the general formula (I)

in which
X is an m-valent organic radical obtained by removing primary amino groups from a corresponding polyamine 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., wherein the m-valent organic radical optionally contains one or more heteroatoms, and wherein the corresponding polyamine comprises aromatically, (cyclo)aliphatically, or araliphatically attached primary amino groups,
R1 and R2 are identical or different organic radicals each having 1 to 18 carbon atoms,
m is an integer >1,

by combining substituted maleic or fumaric esters of the general formula (II)
R1OOC—CH═CH—COOR2  (II),

with primary polyamines of the general formula (III)
X—(—NH 2 ) m   (III),

to form the polyaspartic ester of the general formula (I); and
purifying the polyaspartic acid ester to form the polyaspartic ester composition of claim 1 , wherein purifying comprises distillation that is carried out at a pressure below 20 mbar and a temperature below 180° C. using a distillation apparatus selected from a falling-film evaporator, a thin-film evaporator, a short-path evaporator, or a combination thereof and further comprises cooling a bottom outflow containing a purified polyaspartic ester to a temperature below 100° C. immediately after leaving the distillation apparatus.

3. The process as claimed in claim 2 , wherein
a) distillation is carried out at a pressure between 0.005 and 2 mbar and
b) a temperature of the bottom outflow upon exiting the distillation apparatus is ≤170° C. and ≤a temperature resulting from formula (IV) below:
T (bottom outflow)=27×ln( p )+150  (IV),

where T(bottom outflow) is the temperature of the bottom outflow in ° C. and
p is a pressure in the distillation apparatus in mbar.

4. The process as claimed in claim 2 , wherein distillation is carried out in two stages using a combination of a thin-film evaporator and subsequent short-path evaporator.

Assignees

• Covestro Deutschland Ag

Inventors

• Greszta-Franz Dorota
• Drumm Christian
• Morbach Jan
• Witkowski Reiner

Classifications

• C07C227/06

  by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid · CPC title

• C09D175/00

  Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers · CPC title

• C07C227/40 Primary

  Separation; Purification · CPC title

• C08G18/3821

  Carboxylic acids; Esters thereof with monohydroxyl compounds · CPC title

• C07C229/24

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