Aminoalcohol compounds and their use as zero or low VOC additives for paints and coatings

a technology of amines and additives, applied in the field of amines, can solve the problems of poor scrub resistance, high odor of such amines, and unsuitability for low odor paint, and achieve the effect of reducing the content of volatile organic compounds

Inactive Publication Date: 2014-08-21
ANGUS CHEM CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0007]We have now found that aminoalcohol compounds of the structures represented below function as highly efficient additives for paints and coatings. For instance, the compounds function as highly efficient neutralizers, and / or as freeze thaw stabilizers. In addition, the compounds may possess a number of other favorable properties that further enhance their applicability in paints and coatings. Advantageously the compounds exhibit either low or no VOC and in some embodiments, very low amine odor.
[0014]In another aspect, there is provided a method for reducing the volatile organic compound content of an aqueous based paint or coating that contains a neutralizing agent or freeze-thaw additive, a binder, a carrier, and a pigment, the method comprising using as the neutralizing agent or the freeze-thaw additive a compound of formula I as described herein.

Problems solved by technology

In addition, when used in an otherwise low VOC paint formulation, the odor of such amines is more noticeable.
However, ammonia, while an efficient neutralizer, has a very strong odor and is therefore unsuitable for use in low odor paint.
Inorganic hydroxides and carbonates are undesirable because they often result in coatings with poor scrub resistance.
Such varying temperatures may result in the paint or coating undergoing one or more freeze-thaw cycles.
Freezing and thawing, however, has a detrimental effect on paint and coatings, unfavorably affecting their performance (e.g., by increasing the viscosity), and sometimes rendering the formulations unusable.
However, these materials may not be desirable because they may be of high VOC and therefore generally not suitable for use in low VOC formulations.

Method used

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  • Aminoalcohol compounds and their use as zero or low VOC additives for paints and coatings
  • Aminoalcohol compounds and their use as zero or low VOC additives for paints and coatings
  • Aminoalcohol compounds and their use as zero or low VOC additives for paints and coatings

Examples

Experimental program
Comparison scheme
Effect test

example 1

3,3′-((((2,3-dihydroxypropyl)azanediyl)bis(ethane-2,1-diyl))bis(azanediyl))bis(propane-1,2-diol) (DETA-Glyc)

[0076]A 3-neck round bottom flask equipped with a magnetic stirrer, nitrogen blanket, thermocouple controlled heating mantle and addition funnel is charged with diethylene triamine (103 g, 1 mole, 1.0 equivalent) and 100 mL of water. A slight exotherm is observed during the mixing of the amine and water. Once the exotherm subsides, the addition funnel is charged with 96% pure Glycidol (192.5 g (174 mL), 2.5 moles, 2.5 equivalent) and added very slowly to the amine / water solution. The reaction is extremely exothermic and therefore, slow addition of the alkylene oxide will control the reaction temperature. The reaction has been run at 25° C. (control temperature by slow addition and ice-bath), 60° C. (control temperature by slow addition and ice-bath) and at 85° C. (control temperature by slow addition). In all cases, the reaction products are similar. Addition of Glycidol to th...

example 2

1,1′-((((2-hydroxypropyl)azanediyl)bis(ethane-2,1-diyl))bis((2-aminoethyl)azanediyl))bis(propan-2-ol) (TEPA-3PO)

[0077]Using tetraethylene pentamine (0.5 mol) and propylene oxide (1.5 mol) as starting materials and following analogous procedures to those described above, the title compound may be prepared. LC / MS analyses show component masses ranging from 363 to 537 daltons. IR shows OH and NH2 at 3294 cm−1, aliphatic CH at 2962 and 2815 cm−1, and aliphatic CH2 and CH3 at 1456, 1370, 1334, 1293, 1133, 1061, 1013, 944, and 842 cm−1. 1H-NMR shows a broad singlet at 3.836 ppm (2.5 Hs), a complex multiplet at 2.724-2.308 ppm (22 Hs), and a complex multiplet at 1.168-1.092 ppm (9 Hs). 13H-NMR showed 13 signals at 77.175-73.531 ppm, 4 signals at 68.508-67.271 ppm, 7 signals at 65.667-62.911 ppm, 10 signals at 60.326-56.966 ppm, single signals at 51.935 and 50.255 ppm, and 6 signals at 31.960-30.842 ppm.

example 3

7,13-bis(2-hydroxypropyl)-4,7,10,13,16-pentaazanonadecane-2,18-diol (TEPA-4PO)

[0078]Using tetraethylene pentamine (0.5 mol) and propylene oxide (2.0 mol) as starting materials and following analogous procedures to those described above, the title compound may be prepared. The IR and NMR analysis results are similar to those obtained for TEPA-3PO.

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Abstract

Provided are aminoalcohol compounds for use as additives in paints and coatings. The compounds are of the formula I: wherein p, m, n, R, R1, R2, R3, R4, R5, and R6 are as defined herein.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application claims priority from U.S. provisional application Ser. No. 61 / 512,628, filed Jul. 28, 2011, and from Indian application serial number 1342 / CHE / 2012, filed Apr. 3, 2012, which are incorporated herein by reference.BACKGROUND[0002]This invention relates generally to aminoalcohol compounds and their use as low odor, zero or low volatile organic content (VOC) additives for paints and coatings.[0003]Organic amines are used in aqueous based paints as neutralizing agents. In many geographies, paint manufacturers are facing regulations to reduce the volatile organic content (VOC) of their formulations. Most conventional neutralizing amines are 100% volatile and are therefore VOC contributors. In addition, when used in an otherwise low VOC paint formulation, the odor of such amines is more noticeable.[0004]Ammonia and inorganic hydroxides and carbonates are potential alternatives for use as neutralizers, that are by definition non-...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C09D7/12
CPCC09D7/1233C07C215/12C09D5/14A01N25/04A01N33/08C07C215/14C07C217/28C09D7/63
Inventor PEERA, ASGHARSWEDO, RAYMOND J.GREEN, G. DAVIDBUSCHE, ESIN G.QUINN, JOHN W.BHIDE, SHREYASSAWANT, MAHESH
Owner ANGUS CHEM CO
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