Aminoalcohol compounds and their use as zero or low VOC additives for paints and coatings
View Patent ↗Provided are aminoalcohol compounds for use as additives for paints and coatings. The compounds are of the formula (I): wherein x, R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R A are as defined herein.
1. A compound of formula I:
wherein x is 0, 1, or 2;
R A is OH or alkyl;
R is CH 2 CHR 1 OH, and R 1 is an unsubstituted alkyl, unsubstituted cycloalkyl, phenyl, phenyl-alkyl-, or alkoxyalkyl-, wherein the alkoxy group is 1 to 4 carbon atoms;
R 2 is H, alkyl, cycloalkyl, hydroxyalkyl, or independently R;
R 3 and R 4 are independently alkyl, cycloalkyl, phenyl, or hydroxyalkyl, or R 3 and R 4 , together with the carbon to which they are attached, form cycloalkyl; and
R 5 and R 6 are independently H or alkyl, or R 5 and R 6 , together with the carbon to which they are attached, form cycloalkyl,
or, when x is 0, R 3 and R 5 , together with the carbon atoms to which they are attached, form cycloalkyl; and
provided that when x is 0, R A is OH and when x is 1 or 2, R A is alkyl.
2. The compound of claim 1 wherein x is 0 and R 3 and R 4 are independently hydroxyalkyl.
3. The compound of claim 1 wherein x is 0 and R 3 and R 4 are independently alkyl.
4. The compound of claim 1 wherein x is 0, R 3 is alkyl, and R 4 is hydroxyalkyl.
5. The compound of claim 1 wherein R 5 and R 6 are both H.
6. The compound of claim 1 wherein x is 0 and R 3 and R 5 , together with the carbon atoms to which they are attached, form cycloalkyl.
7. The compound of claim 1 wherein x is 1 or 2 and R 3 , R 4 , R 5 , and R 6 are independently alkyl.
8. The compound of claim 1 wherein R 2 is H.
9. The compound of claim 1 wherein R and R 2 are both CH 2 CHR 1 OH.
10. The compound of claim 1 is one of: 1,1′-((1-hydroxy-2-methylpropan-2-yl)azanediyl)bis(propan-2-ol); 1,1′-((1-hydroxy-2-methylpropan-2-yl)azanediyl)bis(butan-2-ol); 2-((2-hydroxybutyl)amino)-2-(hydroxymethyl)propane-1,3-diol; 2-(hydroxymethyl)-2-((2-hydroxypropyl)amino)propane-1,3-diol; 2-ethyl-2-((2-hydroxybutyl)amino)propane-1,3-diol; 2-((2-hydroxy-3isopropoxypropyl)amino)-2-methylpropane-1,3-diol; 2-((2-hydroxy-3-isopropoxypropyl)amino)-2-(hydroxymethyl)propane-1,3-diol; 2-(bis(2-hydroxybutyl)amino)-2-ethylpropane-1,3-diol; or 2-(bis(2-hydroxypropyl)amino)-2-ethylpropane-1,3-diol.
11. An aqueous based paint or coating comprising a binder, a carrier, a pigment, and an additive, wherein the additive is the compound of claim 1 .
12. A compound of formula I:
wherein x is 0;
R A is OH;
R is CH 2 CHR 1 OH, and R 1 is H, an unsubstituted alkyl, cycloalkyl, phenyl, phenyl-alkyl-, or alkoxyalkyl-, wherein the alkoxy group is 1 to 4 carbon atoms;
R 2 is alkyl, cycloalkyl, hydroxyalkyl, or independently R;
R 3 is H, cycloalkyl, phenyl, or hydroxyalkyl;
R 4 is alkyl, cycloalkyl, or phenyl, or R 3 and R 4 , together with the carbon to which they are attached, form cycloalkyl; and
R 5 and R 6 are independently H or an unsubstituted alkyl, or R 5 and R 6 , together with the carbon to which they are attached, form cycloalkyl,
or R 3 and R 5 , together with the carbon atoms to which they are attached, form cycloalkyl.
13. The compound of claim 12 , wherein R and R 2 are both CH 2 CHR 1 OH.
14. The compound of claim 13 , wherein R 1 is H or an unsubstituted C 1-6 alkyl.
15. The compound of claim 12 , wherein R 3 and R 5 , together with the carbon atoms to which they are attached, form cycloalkyl.
16. The compound of claim 12 , wherein R 4 is C 1-6 alkyl.
17. The compound of claim 12 is one of: 2,2′-((2-hydroxycyclohexyl)azanediyl)diethanol or 2-(bis(2-hydroxyethyl)amino)-2-ethylpropane-1,3-diol.
18. An aqueous based paint or coating comprising a binder, a carrier, a pigment, and an additive, wherein the additive is the compound of claim 12 .
19. A compound that is 2,2′-((2-hydroxybutyl)azanediyl)diethanol.
20. An aqueous based paint or coating comprising a binder, a carrier, a pigment, and an additive, wherein the additive is the compound of claim 19 .