Granted Patent B2

US 8,480,800 · App. 12/957,958 · Granted Jul 9, 2013

Abstract

Claims (44)

1. A compound of formula I:

or a salt thereof, wherein n at all occurrences is 1;

R 1 is H or C 1 -C 10 alkyl, R 2 is C 1 -C 10 alkyl, or R 1 and R 2 , together with the carbon to which they are attached, form a C 3 -C 12 cycloalkyl ring optionally substituted with C 1 -C 6 alkyl;

R 3 is H, C 1 -C 10 alkyl, or phenyl;

R 4 is H, C 1 -C 10 alkyl optionally substituted with hydroxy, -(C(R 6 )(R 7 )) m —N(R 8 )(R 9 ), or Y, wherein m is an integer from 1 to 6, and R 6 and R 7 are independently H or C 1 -C 10 alkyl;

R 5 , R 8 , and R 9 are independently H, C 1 -C 10 alkyl optionally substituted with hydroxy, or Y; and

Y is a group of formula:

2. A compound according to claim 1 wherein:

R 4 ═—(C(R 6 )(R 7 )) m —N(R 8 )(R 9 );

R 5 ═R 8 ═H or C 1 -C 10 alkyl; and

R 9 ═H.

3. A compound according to claim 1 wherein:

R 4 ═—(C(R 6 )(R 7 )) m —N(R 8 )(R 9 );

R 5 ═R 8 ═H or C 1 -C 10 alkyl; and

R 9 ═Y.

4. A compound according to claim 1 wherein:

R 4 ═—(C(R 6 )(R 7 )) m —N(R 8 )(R 9 );

R 5 ═H or C 1 -C 10 alkyl; and

R 8 ═R 9 ═Y.

5. A compound according to claim 1 wherein:

R 4 ═—(C(R 6 )(R 7 )) m —N(R 8 )(R 9 ); and

R 5 ═R 8 ═R 9 ═Y.

6. A compound according to claim 1 wherein:

R 4 ═H or C 1 -C 10 alkyl optionally substituted with hydroxy; and

R 5 ═C 1 -C 10 alkyl substituted with hydroxy.

7. A compound according to claim 1 wherein:

R 4 ═Y; and

R 5 ═C 1 -C 10 alkyl substituted with hydroxy.

8. A compound according to according to claim 1 wherein R 4 ═R 5 ═Y.

9. A compound according to claim 1 selected from the group consisting of:

1,1′-(ethane-1,2-diylbis(methylazanediyl))bis(4-amino-4-methylpentan-2-ol); 1,1′-(2-hydroxyethylazanediyl)bis(4-amino-4-methylpentan-2-ol); 3,3′-(ethane-1,2-diylbis(methylazanediyl))bis(1-(1-aminocyclohexyl)propan-2-ol); 1-(1-aminocyclohexyl)-3-((2-hydroxyethyl)(methyl)amino)propan-2-ol; 4-amino-1-((2-hydroxyethyl)(methyl)amino)-4-methylpentan-2-ol; 2,2′-(3-(1-aminocyclohexyl)-2-hydroxypropylazanediyl) diethanol; 2,2′(4-amino-2-hydroxy-4-methylpentylazanediyl)diethanol; 4-amino-1-(2-hydroxyethylamino)-4-methylpentan-2-ol; 4-amino-4-methyl-1-(methyl(2-(methylamino)ethyl)amino)pentan-2-ol; 4-amino-1-(1-hydroxy-2-methylpropan-2-ylamino)-4-methylpentan-2-ol; 1,1′,1″,1′″-(hexane-1,6-diylbis(azanetriyl))tetrakis(4-amino-4-methylpentan-2-ol); and mixtures of two or more thereof.

10. An aqueous based paint or coating comprising a neutralizing agent, a binder, a carrier, and a pigment, wherein the neutralizing agent is a compound according to claim 1 .

11. The aqueous based paint or coating according to claim 10 further comprising one or more additional ingredients selected from: leveling agents, surfactants, thickeners, rheology modifiers, co-solvents, corrosion inhibitors, defoamers, co-dispersants, additional aminoalcohol compounds, and biocides.

12. A process for making a compound according to claim 1 the process comprising:

(a) combining a nitroalkyloxirane compound of formula III:

wherein n at all occurrences is 1; R 1 is H or C 1 -C 10 alkyl, R 2 is C 1 -C 10 alkyl, or R 1 and R 2 , together with the carbon to which they are attached, from a C 3 -C 12 cycloalkyl ring optionally substituted with C 1 -C 6 alkyl; and R 3 is H, C 1 -C 10 alkyl or phenyl;

with an amine of formula HNR 10 R 11 , wherein R 11 is H, or C 1 -C 10 alkyl optionally substituted with hydroxyl; and

R 10 is H, C 1 -C 10 alkyl optionally substituted with hydroxy, or —(C(R 6 )(R 7 )) m —N(R 12 )(R 13 ), wherein m is an integer from 1 to 6, and R 6 and R 7 are independently H or C 1 -C 10 alkyl, and R 12 and R 13 are independently H or C 1 -C 10 alkyl optionally substituted with hydroxy

to form a compound of formula II:

wherein R 4 is H C 1 -C 10 alkyl optionally substituted with hydroxy, —(C(R 6 )(R 7 )) m —N(R 8 )(R 9 ), or Y′: R 5 , R 8 , and R 9 are independently H, C 1 -C 10 alkyl optionally substituted with hydroxy, or Y′; and Y′ is a group of formula:

 and

(b) contacting the product of step (a) with a reducing agent capable of reducing nitro groups.

13. The process according to claim 12 wherein the nitroalkyloxirane compound of formula III is used at a molar excess relative to the amine.

14. A method for reducing a volatile organic compound content of an aqueous based paint or coating that contains a neutralizing agent, a binder, a carrier, and a pigment, the method comprising using as the neutralizing agent an effective amount of a compound according to claim 1 .

Assignments (8)