WO1995031487A1

WO1995031487A1 - Air-drying coatings: methods and compositions

Info

Publication number: WO1995031487A1
Application number: PCT/US1995/005994
Authority: WO
Inventors: Patrick E. Brutto; Thomas H. Marman; Jeannine H. Thielmann
Original assignee: Angus Chemical Company
Priority date: 1994-05-17
Filing date: 1995-05-12
Publication date: 1995-11-23
Also published as: AU2588395A

Abstract

The present invention is directed to a method of reducing the volatile organic content of an air-drying coating by admixing an alkoxylated organic amine with the coating. An alkoxylated organic amine is prepared by exposing alkylene oxide to an organic amine with structure (a), wherein R1, R2, R3 are individually a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a straight chain or branched chain alkyl group or aryl group; a methanol group, an ethanol group, a propanol group, a butanol group, or a straight chain or branched chain alcohol group; or an aminomethane group, an aminoethane group, an aminopropane group, an aminobutane group, aminoalkane group or an aminoaryl group. The alkoxylated organic amines of the present invention include ethoxylated and propoxylated diethylaminoethanol, monoethanolamine, monoisopropanolamine, dimethylethanolamine, propanediamine, propylenediamine, diethylenetriamine and 2-amino-2-methyl-1-propanol. The air-drying coating can be an architectural coating. The air-drying coating can also be a latex architectural coating. The present invention is also directed to a composition of an air drying coating with reduced or low VOC. The reduced or low VOC air-drying coating of the present invention includes ethoxylated or propoxylated organic amines.

Description

AIR-DRYING COATINGS: METHODS AND COMPOSITIONS Field of the Invention

The present invention is generally related to methods and compositions of air- drying coatings with reduced or low volatile organic content. In particular, the present invention relates to methods of reducing the volatile organic content of an air- drying coating by admixing the coating with an alkoxylated organic amine. The present invention also relates to compositions of air-drying coatings with reduced or low volatile organic content which contain alkoxylated organic amines. Background of the Invention

Coatings are formulations in which binders are solubilized, dispersed or emulsified in a solvent. Upon evaporation of the solvent after application, the binders interlock or bind to each other in some fashion to form a continuous and uniform film. Typical binders include organic polymers or resins, and latex emulsions. The characterization of a coating as a solution, dispersion or emulsion is determined by the choice of the binder. A latex coating contains emulsion particles on the order of around 1000 Angstroms. The binders used in typical latex emulsions are vinyl acrylics, acrylics or styrene acrylics.

Coatings are divided into two broad categories, industrial coatings and architectural coatings. Industrial coatings are applied to manufactured items such as refrigerators and automobiles by the manufacturer. Industrial coatings are applied at the factory where the items are manufactured and require special techniques for applying and drying. Typically, industrial coatings are dried by baking the manufactured item in an oven after application. Architectural coatings, in contrast, are intended for on-site application to the interior or exterior surfaces of buildings or other structures. Architectural paints are applied at ambient temperatures and are air- dried.

In the past, both architectural and industrial coatings relied heavily on the use of organic solvents to solubilize the binder and other components of the coating. After application, the coating dried as the organic solvents were allowed to evaporate into the atmosphere. Most organic compounds which evaporate into the atmosphere are known as volatile organic compounds (VOC) in the art. Once released into the atmosphere, volatile organic compounds can cause far reaching environmental damage. Recently, there has been much interest in reducing the amount of volatile organic compounds released into the atmosphere. The United States Environmental Protection Agency (EPA) estimated that 31 million tons of volatile organic compounds were released into the atmosphere in the United States alone in 1975. There is therefore a need for air-drying architectural and industrial coatings with reduced or low VOC emissions.

Recently, the EPA proposed sweeping regulations aimed at lowering VOC emissions from architectural and industrial coatings. (Banov, Able and Maty, Joe, EPA to weigh VOC-rule revisions, American Paint and Coatings Journal, 22, February 14, 1994.) The EPA plan calls for a 25% VOC reduction by 1996, followed by further 10% reductions in the years 2000 and 2003. The plan includes VOC limits for 41 different coating categories.

In an industrial setting, emissions of volatile organic solvents can be controlled through the use of available technology including incinerators, absorbers, scrubbers and condensers. This is possible because the source of the emissions is fixed and constant. Unfortunately, these technologies are expensive to implement and expensive to operate. With architectural coatings, because entire buildings or rooms are painted, the use of these emissions reducing technologies is impractical or impossible. To reduce the VOC of architectural and industrial coatings, coatings manufacturers have formulated water-based coatings. Despite the use of water as the solvent, water-based coatings available today are still not considered reduced, low or zero VOC because significant amounts of volatile organic compounds must still be used to solubilize the components and impart useful characteristics to the coating. In water-based coatings, volatile organic compounds are used as dispersants, thickeners, coalescing agents, biocides, wetting agents, defoamers, binder neutralizers, and freeze-thaw stabilizers.

In water-based industrial coatings, insoluble binders, known as alkyd resins, long polymers that contain numerous carboxyl groups are used. Without further processing, the alkyd resins are not soluble in water. The resin is made soluble in water by neutralization of the carboxyl groups with amines or hydroxides. German patent application D7215 (Fischer) discloses the use of trialkyl amines to neutralize alkyd resins in a water-based, oven-baked industrial coating. Specifically, Fischer discloses the use of ethoxylated 2-amino-2-methyl-l -propanol in an oven-baked industrial coating.

Architectural coatings typically use latex particles as the binder. Latex particles are large micelles of polymers which are not solubilized by water. Latex particles are emulsified by surfactants and the resulting coatings are emulsions of latex particles. Latex particles can be acidic or alkaline. Vinyl acrylic polymers are typically acidic latex particles while acrylic polymers are typically alkaline latex particles. Because architectural coatings use acidic or alkaline latex particles, they must be pH buffered to form useful films. Without buffering, latex coatings form unsatisfactory films. The use of amines to buffer architectural coatings are known.

Well known organic amines include diethylaminoethanol, monoethanolamine, dimethylethanolamine, monoisopropanolamine, and 2-amino-2-methyl-l-propanol. However, amines typically used to buffer architectural coatings are volatile and contribute to the emission of volatile organic compounds into the atmosphere.

Because architectural coatings are applied to buildings or other structures, architectural coatings cannot be dried by baking in an oven to reduce the emission of volatile organic compounds; architectural coatings must be air-dried. There is a need for an amine which can pH buffer an air-drying architectural coating and not contribute to the VOC of the architectural coating.

Summary of the Invention

The present invention provides a method of reducing the volatile organic content of an air-drying coating by admixing with the coating an effective amount of an alkoxylated organic amine. Alkoxylated organic amines can be prepared by exposing an alkylene oxide to an organic amine. The organic amines of the present invention have the structure:

R₂

I

R i — N— R₃ wherein R_j, R2, R3 are individually a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a straight chain or branched chain alkyl group, or aryl group; a methanol group, an ethanol group, a propanol group, a butanol group, or a straight chain or branched chain alcohol group; or an aminomethane group, an aminoethane group, an aminopropane group, aminobutane group, an aminoalkane group or aminoaryl group.

Preferred alkoxylated organic amines are ethoxylated organic amines. Preferred ethoxylated organic amines include ethoxylated diethylaminoethanol, ethoxylated monoethanolamine, ethoxylated monoisopropanolamine, ethoxylated dimethylethanolamine, ethoxylated propanediamine, ethoxylated propylenediamine, ethoxylated diethylenetriamine, and ethoxylated 2-amino-2-methyl-l -propanol. Preferably 100 gallons of the coating includes between about 1 to about 20 pounds of an ethoxylated organic amine.

Alternativly, the alkoxylated organic amine of the present invention is a a propoxylated organic amine. Preferred propoxylated organic amines include propoxylated diethylaminoethanol, propoxylated monoethanolamine, propoxylated monoisopropanolamine, propoxylated dimethylethanolamine, propoxylated propanediamine, propoxylated propylenediamine, propoxylated diethylenetriamine, and propoxylated 2-amino-2-methyl-l -propanol. Preferably 100 gallons of the coating includes between about 1 to about 20 pounds of a propoxylated organic amine.

The preferred method of alkoxylating an organic amine is by exposing an alkylene oxide to an organic amine. Preferably, in the preparation of an alkoxylated organic amine the molar ratio of the organic amine to alkylene oxide can be varied from about 1:1 to about 1:10.

In preparing an ethoxylated or propoxylated organic amine, an organic amine is exposed to ethylene oxide or to propylene oxide. Preferably, in the preparation of an ethoxylated or propoxylated organic amine the molar ratio of the organic amine to alkylene oxide can be varied from about 1:1 to about 1:10. A further aspect of the present invention provides an air-drying coating composition with reduced or low volatile organic content comprising a binder, a solvent and an alkoxylated organic amine. Preferably, the alkoxylated organic amine is an ethoxylated organic amine or a propoxylated organic amine. In another aspect, 100 gallons of the air-drying coating includes between about 1 to about 20 pounds of an ethoxylated organic amine or a propoxylated organic amine.

In another aspect, the composition of a coating of the present invention is an air-drying architectural coating that includes an alkoxylated organic amine. In a preferred embodiment, the architectural coating is a latex coating.

Detailed Description of the Invention

The present invention provides a method of reducing the volatile organic content of an air-drying coating by admixing with the coating an effective amount of an alkoxylated organic amine.

The alkoxylation of an organic amine can be accomplished by exposing alkylene oxide to an organic amine of interest. In this reaction, a carbon-oxygen bond of the epoxide linkage of the alkylene oxide is replaced by a covalent nitrogen- carbon bond between the organic amine and the alkylene oxide. The reaction is illustrated in reaction I below.

R _\" o

/ \ R" R" H R" H R"

I / \ I

R'— NH + H₂C CHR'" τ> R'-N - C-C- OH + R'-N - C- C- OH

^/ I I I I

H H H H

( i ) ₍ π ) <^m > ^{( i )}

REACTION I Alternatively, if the organic amine includes hydroxyl groups, the carbon- oxygen bond of the epoxide linkage can be replaced by a covalent oxygen-carbon bond between the organic amine and the alkylene oxide as shown in Reaction II.

R'- N-R^- OH -f- H₂C CHR"" ^ R'— N— R'"— O— CH ₂— CHR^'OH

R" R" ( V ) ( VI ) (vπ)

REACTION π

The organic amines contemplated by the present invention have the structure:

Rz

I

R i — N — R₃

wherein R_j, R2, R3 are individually a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a straight chain or branched chain alkyl group or aryl group; a methanol group, an ethanol group, a propanol group, a butanol group, a straight chain or branched chain alcohol group; or an aminomethane group, an aminoethane group, an aminopropane group, an aminobutane group, an aminoalkane group or aminoaryl group. Preferably, an organic amine of the present invention includes diethylaminoethanol, monoethanolamine, monoisopropanolamine, dimethylethanolamine, propanediamine, propylenediamine, diethylenetriamine, or 2- amino-2-methyl- 1 -propanol . As a specific example of the alkoxylation of an organic amine, the ethoxylation of 2-amino-2-methyl-l -propanol is shown in reaction III below. Ethoxylated 2-amino-2-methyl-l -propanol can be prepared by exposing 2-amino-2- methyl-1 -propanol (compound VIII) to ethylene oxide (compound IX) as shown in Reaction III.

HOH₂C— H₂C_{χ /}CHa- CHaOH

NH₂ /°\ N

I / \ I

H₃C— C — CH₂OH + H₂C CH₂ τ> H₃C— C — CH₂OH

I I

CH ₃ CH ₃

( vm ) ( K ) ( X )

REACTION ffl

The structure of an ethoxylated 2-amino-2-methyl-l -propanol can vary according to the reaction conditions under which it is prepared. The first two molecules of ethylene oxide (EO) to react under reaction conditions described herein, replace the hydrogens on the nitrogen atom of 2-amino-2-methyl-l -propanol to form N-(di-2-hydroxyethyl)-2-amino-2-methyl-l -propanol (compound X). Subsequent molecules of ethylene oxide which react with N-(di-2- hydroxyethyl)-2-amino-2-methyl-l -propanol can react with any of the three available hydroxyl groups forming various ether linkages. Thus if 4 molecules of ethylene oxide react with one molecule of 2-amino-2-methyl-l -propanol (AMP™) there are at least three different species possible. Furthermore, when more than 1 molecule of ethylene oxide reacts with one molecule of 2-amino-2-methyl-l -propanol a range of products is observed. For example, in the reaction between 4 moles of EO and 1 mole of 2-amino-2-methyl-l-propanol, the predominant products are ethoxylated 2- amino-2-methyl-l -propanol containing 3 and 4 EO groups. However, other ethoxylated 2-amino-2-methyl-l -propanol products which contain between one or more EO groups are also obtained. As used herein, AMP^™-XEO designates all of the ethoxylated 2-amino-2-methyl-l -propanol products obtained when X moles of ethylene oxide is exposed to one mole of 2-amino-2-methyl-l -propanol. For example, AMP™_4EO designates all of the ethoxylated 2-amino-2-methyl-l -propanol products which are obtained by exposing 4 moles of EO to 1 mole of 2-amino-2- methyl- 1 -propanol .

Other ethoxylated organic amines are contemplated by the present invention. Preferred ethoxylated organic amines include ethoxylated diethylaminoethanol, ethoxylated monoethanolamine, ethoxylated monoisopropanolamine, ethoxylated dimethylethanolamine, ethoxylated propanediamine, ethoxylated propylenediamine, ethoxylated diethylenetriamine, and ethoxylated 2-amino-2-methyl-l -propanol.

A preferred synthetic procedure for ethoxylating organic amines is discussed in Example 1 herein. Briefly 2-amino-2-methyl-l -propanol is exposed to ethylene oxide in an autoclave under a nitrogen blanket. In one embodiment, ethoxylated 2- amino-2-methyl-l -propanol is prepared by exposing 2-amino-2-methyl-l -propanol to ethylene oxide in a molar ratio of about 1:(1-10). In a preferred embodiment, the molar ratio of 2-amino-2-methyl-l -propanol to ethylene oxide is about 1:4. Other means of preparing ethoxylated 2-amino-2-methyl-l -propanol are well known to those of skill in the art.

In another aspect, the present invention provides a method of using propoxylated organic amines to reduce or lower the VOC of an air-drying coating. Organic amines can be propoxylated under reaction conditions discussed above for ethoxylating organic amines. Preferred propoxylated organic amines include propoxylated diethylaminoethanol, propoxylated monoethanolamine, propoxylated monoisopropanolamine, propoxylated dimethylethanolamine, propoxylated propanediamine, propoxylated propylenediamine, propoxylated diethylenetriamine, and propoxylated 2-amino-2-methyl-l-propanol. The use of amines to buffer latex particles is known and used commercially.

The use of amines is useful in that coating properties such as yellowing, pH stability, hiding power, scrub resistance and other properties of the coating are improved or are not adversely affected by the use of these amines. Well-known commercially used amines include 2-amino-2-methyl-l -propanol (AMP^™), monoethanolamine (MEA), monoisopropanolamine (MIPA), dimethylethanolamine (DMEA) and diethylaminoethanol (DEAE). Most commercially used amines are volatile and contribute to the VOC of the coating. As provided by the present invention, ethoxylated 2-amino-2-methyl-l -propanol is not volatile or its volatility is not detectable by current testing protocols. A volatility testing protocol is described in Example 2. This protocol (AΛTM D3960-87) is published by the American Society for Testing and Materials (ASTM) and is the accepted standard volatility testing protocol in the art. It is understood in the art, that the ASTM volatility testing protocol is not useful for samples with a volatility of less than 50 g/1. The volatility of samples with a VOC of less than 50 g/1 is within the detection limits of the testing protocol. Samples with a volatility of less than 50 g/1 are considered to be a no VOC sample in the art. As disclosed in Example 1 , AMP™-4EO is a no VOC compound. The VOC values of AMP -4EO of the present invention ranged from -6 to 31 and are within the detection limits of ASTM D3960-87.

In one aspect, the present invention provides a method of reducing the volatile organic content of an air-drying coating by admixing the coating with an effective amount of an alkoxylated organic amine. Organic amines contemplated by the present invention have the structure:

R₂

I

R i — N — R₃

wherein R_j, R2, R3 are individually a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a straight chain or branched chain alkyl group or aryl group; a methanol group, an ethanol group, a propanol group, a butanol group, or a straight chain or branched chain alcohol group; or an aminomethane group, an aminoethane group, an aminopropane group, an aminobutane group, an aminoalkane group or amino-aryl group. Preferably, an organic amine of the present invention includes diethylaminoethanol, monoethanolamine, monoisopropanolamine, dimethylethanolamine, propanediamine, propylenediamine, diethylenetriamine, or 2- amino-2-methyl- 1 -propanol . In a preferred embodiment, the alkoxylated organic amines of the present invention is an ethoxylated organic amine or a propoxylated organic amine. Preferred ethoxylated organic amines include ethoxylated diethylaminoethanol, ethoxylated monoethanolamine, ethoxylated monoisopropanolamine, ethoxylated dimethylethanolamine, ethoxylated propanediamine, ethoxylated propylenediamine, ethoxylated diethylenetriamine, and ethoxylated 2-amino-2-methyl-l-propanol. Preferred propoxyalted organic amines include propoxylated diethylaminoethanol, propoxylated monoethanolamine, propoxylated monoisopropanolamine, propoxylated dimethylethanolamine, propoxylated propanediamine, propoxylated propylenediamine, propoxylated diethylenetriamine, and propoxylated 2-amino-2-methyl-l -propanol.

In one embodiment, the air-drying coating of the present invention is an architectural coating. In a preferred embodiment, the air-drying coating is an architectural latex coating.

The effective amount of alkoxylated organic amine is that amount sufficient to reduce the VOC of a coating. Preferably, in 100 gallons of the coating, the effective amount of an alkoxylated organic amine is between about 1 to about 20 pounds of the ethoxylated organic amine.

In yet another aspect, the present invention discloses the composition of an air-drying architectural coating that includes ethoxylated 2-amino-2-methyl-l- propanol. Two architectural coatings which include ethoxylated 2-amino-2-methyl-l- propanol are disclosed below. The composition of a vinyl acrylic latex emulsion coating, CB-1, is disclosed in Table 1 below. The composition of an acrylic latex emulsion coating, TB67A, is disclosed in Table 2 below.

TABLE 1 : Interior Flat CB-1 TABLE 2: Exterior Flat TB67A lb*/ '100 lbs/100 gallons gallons

Water 217.28 Water 183.51

Tamol 960^® 3.10 QP- 15000^® 4.25

KTPP^® 2.00 AMP^w-4EO 1 .80

Ethylene Glycol 18.30 Tamol 983^® 2.33

Colloid 643^® 2.00 igepal CO-630^® 1 .84

AMP™-4EO 2.00-1 1 .00 Nopco NDW^® 1 .50

TT-935^® 1 1 .00 RCL-2^® 229.39

R-902^® 196.69 Minspar 4^® 137.63

ASP- 170^® 147.59 Optiwhite^® 45.88

Snowflake^® 196.69

Water 154.99 Water 145.00

Texanol^® 9.10 Ethylene Glycol 22.94

Nuosept 95^® 1 .00 CANGUARD 327^® 1 .38

Triton N-101^® 2.90 Texanol^® 1 1 .56

Colloid 643^® 2.00 L-475^® 1 .84

76 Res 3077^® 237.98 Rhoplex AC-264^® 334.09

Water 10.91 Triton GR-7M^® 0.92

AMP^w-4EO 1.20

Tamol 960^® is a registered trademark of Rohm & Haas Company. KTPP^® is a registered trademark of FMC Corporation. Colloid 643^® is a registered trademark of Rhone Poulenc. AMP™ is a registered trademark of Angus Chemical Company. TT-935^® is a registered trademark of Rohm & Company. R-902^® is a registered trademark of E.I. DuPont de Nemours. ASP-170^® is a registered trademark of Englehard Corporation. Snowflake^® is a registered trademark of ECC America, Inc. Texanol^® is a registered trademark of Eastman Kodak. Nuosept^® is a registered trademark of Hϋls America, Inc. Triton N-101^® is a registered trademark of Union Carbide Corporation. 76 Res 3077^® is a registered trademark of Rohm & Haas Company. QP-15000^® is a registered trademark of Union Carbide Corporation. Tamol 983^® is a registered trademark of Rohm & Haas Company. Igepal CO-630^® is a registered trademark of Rhone Poulenc. Nopco NDW^® is a registered trademark of Henkel Corporation. RCL-2^® is a registered trademark of SCM Pigments, Chemical Division. Minspar 4^® is a registered trademark of the Minspar Division of Kentucky Tennessee Fieldspar. Optiwhite^® is a registered trademark of Burgess Pigment Co. CANGUARD 327^® is a registered trademark of ANGUS Chemical Company. L-475^® is a registered trademark of Drew Industrial Division. Rhoplex AC-264^® is a registered trademark of Rohm & Haas Company. Triton GR-7M^® is a registered trademark of Rohm & Haas Company. The following examples are presented to describe preferred embodiments and utilities of the present invention. While the invention is susceptible to various modifications and alternative forms, specific embodiments thereof have been shown by way of example and were herein described in detail. It should be understood, however, that it is not intended to limit the invention to the particular forms disclosed, but on the contrary, the intention is to cover all modifications, equivalents, and alternatives falling within the spirit and scope of the invention as defined by the appended claims. EXAMPLES Example 1; Synthesis and Physical Properties of Ethoxylated 2-amino-2-methyl-l- propanol

A 2 liter autoclave was charged with 2-amino-2-methyl-l -propanol (AMP^™) or AMP™-95. AMP^™-95 is AMP^™ with 5% water. To the autoclave was added 0.1 % of KOH (45% aqueous), based on total reactants, and the autoclave was sealed and purged with Nitrogen. The 2-amino-2-methyl-l-propanol/KOH was heated to 50°C while stirring at 600 ipm. The autoclave was charged with the theoretical amount of ethylene oxide (EO) in 30 minutes. The autoclave was gradually heated to 80°C while maintaining pressure < 80 psig. The autoclave was held at 80 °C until EO pressure in reactor stabilized (< 30 psig). The total reaction time is around 7 hours. The autoclave was then purged with nitrogen and cooled to 25 °C. The product was analyzed by GC/MS.

The number of ethoxyl groups covalently attached to 2-amino-2-methyl-l- propanol in the above reaction varies according to a rough bell-shaped curve. When the molar ratio of EO to 2-amino-2-methyl-l -propanol is 4: 1, the predominant products obtained are 2-amino-2-methyl-l -propanol ethoxylated with 3 or 4 ethoxyl groups (about 70%). There is also obtained 2-amino-2-methyl-l -propanol ethoxylated with 5 ethoxyl groups (about 5% to 15%) and lesser amounts of product containing between 1 to 2 ethoxyl groups. Samples of AMP^™-4EO prepared from AMP™-95 or 2-amino-2-methyl-l -propanol had similar compositions. Aging ethoxylated 2-amino- 2-methyl-l -propanol for 39 days at 50 °C produced minimal change in the composition.

The pKa of AMP^™-4EO was determined to be about 8.45. PHYSICAL PROPERTIES

Boiling Point 296° C Evaporation Rate Nil (Note 1 ) (n-Butyl Acetate = 1.00)

Vapor Pressure by Temperature °C Isoteniscope, torr

10 (0.94 x 10^"2)

20 (0.19 x 10^'1 )

25 (0.28 x 10^"1 )

30 (0.39 x 10^"1 )

40 (0.80 x 10^"1 )

50 0.15

60 0.26

70 0.47

80 0.78

90 1.3

100 2.0

110 3.1

Note 1 : Sample gained 0.62% weight when suspended on Whatman No. 42 filter paper for 1 hour at 25 °C.

VOC of commercially used amines and ethoxylated 2-amino-2-methyl-l -propanol

The following table lists the VOC of commercially used amines and ethoxylated 2-amino-2-methyl-l-propanol. The VOC is determined as described in Example 2. As shown in the table below, the VOC AMP^™-4EO is less than the detection limits of currently used VOC testing protocols. AMP^™-4EO is therefore a no VOC amine. Aging AMP^™-4EO for 39 days at 50°C, produced very little change in the VOC of the samples of AMP^™-4EO.

Commercially Used Amines AMP'"-1EO A P™-2Eθ AMP'"-3Eθ A P'"-4EO voc 924 954 882 878 286 56 30 Below Detection

(grams liter) Limits Example 2: Testing Protocols VOC Determination

The VOC of a coating _s determined by standard procedures known in the art. These procedures are outlined in ASTM D3960-89. Briefly, the total volatiles of a coating is determined by placing a designated quantity of coating specimen into an aluminum foil dish containing 3 ml of an appropriate solvent (typically, toluene or 2- ethoxyethyl acetate). The coating specimen is weighed, dispersed, and then heated in an oven at 110 ± 5°C for 60 min. After 60 min, the aluminum dish is cooled in a desiccator and weighed. The percent volatile is calculated from the loss in weight. The VOC does not include water and other exempt solvents that are volatile. The percentage of water in the sample is determined by titration using Karl Fisher as outlined in ASTM D4017-90. The weight per gallon of the sample is obtained by using a standard weight-per-gallon cup. The VOC is calculated as follows:

VOCielt₎ = (^% volatiles - % water) (wtlgal) (119.95)

100 - % water

Viscosity Determination

Viscosity determination is performed according to ASTM D562-81 (Reapproved 1990), procedure B. The viscosity of a sample is determined by the load (in grams) required to produce a rotational frequency of 200 r/min (i.e. where the lines appear stationary), for an offset paddle rotor immersed in the sample. The viscosity of two standard oils which are within the viscosity range of the sample to be measured are used to calibrate the viscometer. Suitable standards are silicone, hydrocarbon, linseed, and caster oils. The viscosity of the sample of interest is determined by the use of well known formulas. Gloss Determination The determination of gloss is performed according to ASTM D523-89. Gloss is the capacity of a surface to reflect light. Surfaces typically reflect more light in some directions than in others. The directions associated with mirror (or specular) reflection normally have the highest reflectances. Gloss measurements are typically made with 60°, 20°, or 85° geometry in a parallel-beam glossmeter. A glossmeter consists of a light source and a photodetector. The photodetector measures the light reflected from the sample at Various angles. The measured gloss ratings of a sample are compared to the measured gloss ratings of a black glass standard. Whiteness and Yellowness Determination

The whiteness and yellowness of a sample is determined according to ASTM E313-73 (Reapproved 1987). Whiteness is the attribute by which an object color is judged to approach a preferred white. Yellowness is the attribute by which an object color is judged to depart from a preferred white toward yellow. The whiteness and yellowness are determined by the use of formulas well known in the art.

The instrumental determinations of whiteness and yellowness of materials are measured with a spectrophotometer or with a colorimeter. The spectrophotometer can be equipped with a tristimulus integrator conforming to Practice E-308, a photoelectric reflectometer conforming to the apparatus specified in Test Method E- 97, or a colorimeter having source, filter, and receptor characteristics such that it will measure the reflectance of white and near-white specimens accurately to within 1.0% of full-scale reading. Determination of Scrub Resistance

The scrub resistance of a sample is determined according to ASTM D2486-89. A 7.0-mil (0.18-mm) film of the test paint is applied to a black plastic panel with a film caster. The film is aged (air dried) in a horizontal position for 7 days at room temperature (73.5 ± 3.5°F (23 ± 2°C) and 50 ± 5% relative humidity). After aging, the coated panel is placed over a V_-in. by 10-mil (12.7 by 0.25-mm) shim and held in place on a glass plate in a washability machine. The film is then scrubbed with a nylon bristle brush and an abrasive scrub medium until failure occurs over the shim. Flash Rusting

To determine the effect of ethoxylated 2-amino-2-methyl-l -propanol on flash rusting, a 3 mil drawdown of each coating was made on cold rolled steel panels. AMP^™-4EO displayed good flash rusting characteristics as shown in the table below.

Flash Rusting

lbs/100 gallons AMP™-4E0 Commercially commercially used Rust Score Used Amine amine or AMP™-4E0 Rust Score

Interior Flat 2.0 7 5

CB-1 3.0 7 6-7

3.5 6-7 7

4.0 6-7 6-7

5.0 6-7 9

7.0 6-7 Undetermined

9.0 9 Undetermined

1 1.0 9 Undetermined

Exterior Fiat 3.0 10(-) 10(-)

TB67A

Key: 10 - Best 1 - Worst

Stability Testing

The paint is prepared and allowed to age overnight. The initial viscosity (ASTM D562) and pH is determined. After aging, two half pint samples of paint are incubated in an oven at 60°C. Two half pint samples are incubated at room temperature as controls.

After two weeks incubation, one sample from the oven is removed and allowed to come to room temperature. The 60 °C sample and one of the samples stored at room temperature are mixed for five minutes on a mixer or shaker. The viscosity and pH of the samples are determined. A sample is considered to pass the stability test if the change in viscosity is no more than ± 10 KU and pH values do not fall below 7.0. A 3 mil drawdown of each stability sample is made on a Leneta opacity chart (Form 3B) and aged for 24 hours. The gloss/sheen (ASTM D523), contrast ratio (ASTM D2805), and whiteness/yellowness index (ASTM E313) are determined. This test was repeated after four weeks of aging with the remaining sample. Biostability

Biostability testing of AMP^™-4EO containing paint was performed to determine if the addition of either AMP^™-4EO or a commercially used amine to a paint containing a preservative had any effect on the biocidal efficacy of the product.

Preservation Testinα Procedure 1. Inoculum:

Bacterial Cultures Source

Pseudomonas aeruginosa ATCC 9027

Pseudomonas aeruginosa ATCC 27853

Enterobacter aerogenes ATCC 13048

Bacillus subtilis Industrial isolate

A composite of the bacteria strains is used for the inoculum. The cultures are maintained on Plate Count Agar and transferred weekly.

Twenty-four hour cultures for each strain are harvested using a sterile cotton- tipped applicator and placed into deionized sterile water. The concentration is determined using the McFarland Nephelometer Standards and is adjusted to o approximately 5 x 10° CFU/ml.

II. Test Samples

Thirty grams of the product under test is weighed into 4 oz. sterile specimen collection cups. If samples do not contain biocide, addition is made now utilizing a Pipetman Automatic Pipettor to deliver the correct amount. Inoculation is made by adding 0.3 ml of the bacteria mixture to each sample and mixing well with a sterile tongue depressor.

III. Evaluation of Bacterial Survival:

The inoculation schedule is as follows: Day 0, Day 2 (after plating sample has been taken), Day 6, and Day 13. Plating is performed at each of the following times: Day 0 (immediately after inoculation), Day 1, Day 2 (before inoculation), Day 3, Day 7, Day 14, Day 21, and Day 28. Test samples are streaked onto Plate Count Agar using a sterile cotton-tipped applicator and incubated at 32 °C for 48 hours. Bacterial survival is rated using the following criteria: Plating Results Score CFU/ml

No detectable survival 0 0

1-4 colonies 1 10

5-20 colonies 2 10²

20-100 colonies 3 10³

Too numerous to count 4 10⁶

Since the inoculum used is approximately 5 x 10 CFU per gram of test sample, the expected number of survivors, if no growth or cell death occurs, is about 1 x 10" cfu per sample. No detectable survival, therefore, represents a six-log kill of the inoculated population.

Analysis of the test data, contained in the Table below demonstrates no difference in biocidal efficacy of preserved paints containing either ethoxylated 2- amino-2-methyl-l -propanol or the commercially used amine. At equal levels of biocidal protection from BIOBAN^® N-95, neither AMP^™-4EO or the commercially used amine hindered nor helped the product's resistance towards in-can bacterial attack.

The lower pH of AMP^™-4EO versus commercially used amine control did not exhibit any detrimental effects to the biocidal stability of the paints.

AMP™-4EO vs. Commerically Used Amine Biostability Modified Buono Method In-Can Preservation Test

Test Sample/Biocide Day 0 Day 1 Day 2 Day 3 Day 7 Day 14 Day 21 Statu

1. AMP^w-4EO Paint 4 1 0 0 0 0 0 Pass 1000 ppm (0.1 % wt/wt) BIOBAN N-95^®

2. AMP™-4EO Paint 4 0 0 0 0 0 0 Pass 1500 ppm (0.15% wt/wt) BIOBAN N-95^®

3. AMP™-4EO Paint 4 2 4 4 3 3 4 Fail No Biocide

4. Commercial Amine 4 1 0 0 0 0 0 Pass Paint, 1000 ppm (0.1 % wt/wt) BIOBAN N-95^®

5. Commercial Amine 4 0 0 0 0 0 0 Pass Paint, 1500 ppm (0.15% wt/wt) BIOBAN N-95^®

6. Commercial Amine 4 2 4 3 3 3 4 Fail Paint, No Biocide

Interpretation: 0 = no survival

1 = 1-4 colonies

2 = 5-20 colonies

3 = greater than 20 colonies

4 = too numerous to count

Since the inoculum used is approximately 5 x 10" cfu per gram of test sample, the expected number of survivors, if no growth or cell death occurs, is about 1 X 10⁶ cfu per sample. No detectable survival, therefore, represents a six-log kill of the inoculated population. Reinoculated Day: Day 0, Day 1, Day 2 (after plating), Day 6, and Day 13

Bacterial Inoculum:

Latex "spoiled" bacteria Industrial isolate

Pseudomonas aeruginosa ATTC #9027 Pseudomonas aeruginosa ATTC #27853

Enterobacter aerogenes ATTC #13048

Bacillus subtilis Industrial isolate

Paint spoilage bacteria Industrial isolate

Example 3: Interior Latex Flat CB-1 A commercially used amine and AMP^™-4EO were evaluated in a latex interior coating. Interior latex flat CB-1 contains a vinyl acrylic emulsion (76 Res 3077) and an acrylic alkali swellable thickener (TT-935). Testing included viscosity/pH/sheen stability, contrast ratio, whiteness/yellowness index, and scrub resistance. The formulation of interior latex flat CB-1 is presented in the Table below.

Interior Flat CB-1 lbs/100 gallons lbs/ 100 gallons

Water 217.28 217.28

Tamol 960^® 3.10 3.10 TPP^® 2.00 2.00

Ethylene Glycol 18.30 18.30

Colloid 643^® 2.00 2.00

AMP™-4EO 2.00-1 1.00 0

Commercial Amine 0 2.00-5.00

TT-935^® 11.00 1 1.00

R-902^® 196.69 196.69

ASP- 170^® 147.59 147.59

Snowflake^® 196.69 196.69

Water 154.99 154.99

Texanol^® 9.10 9.10

Nuosept 95^® 1.00 1.00

Triton N-101^® 2.90 2.90

Colloid 643^® 2.00 2.00

76 Res 3077^® 237.98 237.98

Water 10.91 10.91

A ladder study was performed on a commercially used amine and AMP^™-4EO to compare pH development in the interior flat CB-1 system. AMP^™-4EO does not display as much pH development as the commercial amine. This is due to the lower pKa value of AMP™-4EO (8.45) versus the commercial amine (9.72). The pH values ranged from 8.2 at 2.0# AMP™-4EO/100 gallons to 8.8 at 11.0#/100 gallons. The commercially used amine yielded pH values of 8.75 at 2.0#/100 gallons and 9.6 at 5.0#/100 gallons. The scrub resistance of interior flat CB-1 using AMP^™-4EO was comparable to the scrub resistance of interior flat CB-1 system using a commercially used amine. The scrub resistance test was performed as described herein. The number of cycles to failure for interior flat CB-1 containing between 2 and 11 pounds of AMP™-4EO per 100 gallons of paint ranged from 412 to 564. The scrub resistance of AMP™- 4EO interior flat CB-1 formulation is comparable or better than the scrub resistance of an interior flat CB-1 formulation that contains a commercially used amine. The number of cycles to failure for interior flat CB-1 containing between 2 and 5 pounds of the commercially used amine per 100 gallons of paint ranged from 400 to 474.

AMP -4EO displayed comparable viscosity/pH/sheen stability, contrast ratio, scrub resistance, and whiteness/yellowness index compared to the commercially used amine control. These data are presented in Tables below.

Interior Flat CB-1 with a Commercially Used Amine

2.0# 3.0# 3.5# 4.0# S,0#

Viscosity (KU)

Initial 88 83 85 83 81

2 wk RT 86 83 85 83 82

2 wk HS 80 76 78 78 76

4 wk RT 83 80 78 80 79

4 wk HS* 74 72 73 71 70

Δ -14 -1 1 -12 -12 -1 1

PH

Initial 8.75 9.3 9.2 9.5 9.6

2 w RT 8.60 9.2 9.1 9.4 9.5

2 wk HS 8.30 8.8 8.8 9.1 9.2

4 wk RT 8.50 9.1 9.0 9.3 9.5

4 wk HS 8.30 8.5 8.5 8.6 8.8

A -0.45 -0.8 -0.7 -0.9 -0.8

Contrast Ratio

Initial 0.988 0.986 0.986 0.985 0.985

2 wk HS 0.988 0.984 0.987 0.987 0.985

4 wk HS 0.987 0.987 0.988 0.988 0.987

Δ -0.001 -0.002 + 0.002 + 0.003 + 0.002

Whiteness Index

Initial 74.36 73.92 74.28 73.75 73.77

2 wk HS 71.42 71.22 70.68 70.81 70.75

4 wk HS 69.57 69.83 69.29 69.18 68.93

Δ -4.97 -4.09 -4.99 -4.57 -4.84

Yellowness Index

Initial 4.63 4.69 4.56 4.75 4.70

2 wk HS 5.28 5.35 5.46 5.48 5.47

4 wk HS 5.92 5.84 5.95 5.99 6.05

A + 1.29 + 1.15 + 1.39 + 1.24 + 1.35

85° Sheen

Initial 8.6 8.5 7.5 8.9 8.0

2 wk RT 6.6 6.7 6.8 6.9 6.8

2 wk HS 6.8 6.9 6.7 6.5 6.5

4 wk RT 8.4 9.3 7.4 9.7 9.1

4 wk HS 9.1 8.5 8.3 8.1 8.1

Δ -2.0 -1.8 ±0.8 -2.4 -1.5

All samples displayed VSL sep. Interior Flat CB-1 with AMP -4EO

2.0# AMP^EO 3,0# AMp'"-4EO 3.s# AMP" EO 4.0# A P™-4E0 5.0# AMP'"-4EO 7,0# AMP^EO 9.0# AMP"-4Eθ Π.OO AM

4EO

Viscosity ( U)

Initial 80 83 80 77 78 80 80 80

2 wk RT 82 83 78 80 82 82 80 82

2 wk HS 78 76 74 74 76 74 74 76

4 wk RT* 78 79 76 76 77 79 76 78

4 wk HS* 78 73 74 71 73 74 71 72

A ± 2 -10 -6 -6 -5 -6 -9 -8

PH

Initial 8.2 8.35 8.3 8.4 8.5 8.6 8.7 8.8

2 wk RT 8.1 8.25 8.2 8.3 8.4 8.5 8.6 8.7

2 wk HS 7.8 7.90 7.9 8.1 8.2 8.3 8.4 8.6

4 wk RT 8.0 8.20 8.2 8.2 8.3 8.4 8.6 8.7

4 wk HS 7.9 8.00 7.9 8.0 8.1 8.2 8.4 8.5

A -0.4 -0.45 -0.4 -0.4 -0.4 -0.4 -0.3 -0.3

Contrast Ratio

Initial 0.985 0.984 0.986 0.985 0.986 0.985 0.985 0.98

2 wk HS 0.985 0.985 0.986 0.984 0.986 0.984 0.986 0.08

4 wk HS 0.987 0.988 0.988 0.986 0.984 0.986 0.984 0.98

A + 0.002 + 0.004 + 0.002 ±0.001 -0.002 ± 0.001 ± 0.001 ±0.00

2,o# AMP" EO 3.0# AMP -4EO 3.5# AMP^EO 4.0# AMP^EO S.O# AMP'"-4EO 7.0# AMP"-4EO 9,0# AMP™-4EO 11.0# AM 4EO

Whiteness

Index

74.26 74.27 74.38 74.22 74.32 74.69 73.93 73.97

Initial 72.37 72.43 72.33 72.1 1 72.00 72.08 71.1 1 71.63

2 wk HS 70.02 70.42 70.90 70.29 70.31 70.54 68.57 69.97

4 wk HS -4.24 -3.85 -3.48 -3.93 -4.01 -4.15 -5.36 -4.00 A

Yellowness

Index

4.60 4.61 4.57 4.61 4.58 4.47 4.63 4.67

Initial 5.03 5.06 5.08 5.15 5.18 5.17 5.38 ^* 5.27

2 wk HS 5.76 5.69 5.55 5.68 5.68 5.65 6.08 5.74

4 wk HS + 1.16 + 1.08 + 0.98 + 1.07 + 1.10 + 1.18 + 1.45 + 1.07 A

85° Sheen

Initial 7.1 7.6 7.7 7.6 7.5 7.5 7.6 8.3

2 wk RT 6.0 6.4 6.5 6.5 6.4 6.5 6.3 6.5

2 wk HS 6.4 6.9 6.8 6.9 6.9 6.9 6.9 6.9

4 wk RT 7.1 7.9 7.7 9.0 8.0 8.1 7.5 9.2

4 wk HS 8.4 8.5 8.8 8.5 7.8 9.2 7.9 9.3

A + 1.3 -1.2 -1.2 -1.4 -1.1 + 1.7 + 1.3 -1.8

* All sample displayed VSL sep.

Example 4; Exterior Latex Flat TB67A

Exterior Flat TB67A is a formulation that contains an acrylic emulsion (AC- 264) and a cellulosic thickener (QP- 15000). Testing included viscosity/pH/sheen stability, contrast ratio, whiteness/yellowness index, and scrub resistance. Four weeks of stability testing was completed. The formulation of exterior latex flat TB67A is presented in the Table below.

Exterior Flat TB67A lbs/ 100 gallons lbs/100 gallons

Water 183.51 183.51

QP- 15000^® 4.25 4.25

AMP™-4EO 1 .80 0

Commercial amine 0 1 .80

Tamol 983^® 2.33 2.33

Igepal CO-630^® 1 .84 1 .84

Nopco NDW^® 1 .50 1 .50

RCL-2^® 229.39 229.39

Minspar 4^® 137.63 137.63

Optiwhite^® 45.88 45.88

Water 145.00 145.00

Ethylene Glycol 22.94 22.94

CANGUARD 327^® 1 .38 1 .38

Texanol^® 1 1 .56 1 1 .56

L-475^® 1 .84 1 .84

Rhoplex AC-264^® 334.09 334.09

Triton GR-7M^® 0.92 0.92

AMP™-4EO 1 .20 0

Commercial amine 0 1 .20 In the Exterior Flat TB67A formula, AMP™_4EO performed comparably to the commercially used amine in all areas except pH development. Initial pH for the commercial amine system was 9.8, and for the AMP^™-4EO system was 9.3.

The scrub resistance of exterior flat TB67A using AMP^™-4EO was comparable or better than the scrub resistance of exterior flat TB67A system using the commercially used amine. The scrub resistance test was performed as described herein. The number of cycles to failure for exterior flat TB67A containing 3 pounds of AMP^™-4EO per 100 gallons of paint was 744. The scrub resistance of AMP^™-4EO exterior flat TB67A formulation is comparable to the scrub resistance of the exterior flat TB67A formulation with the commercially used amine. The number of cycles to failure for exterior flat TB67A containing 3 pounds of the commercially used amine per 100 gallons of paint was 794.

AMP^™-4EO displayed comparable viscosity/pH/sheen stability, contrast ratio, scrub resistance, and whiteness/yellowness index compared to the commercially used amine control. These data are presented in Tables below.

Interior Flat TB67A

3.0# commercial aminβ 3.0# AMP™-4E0

Viscosity (KU)

Initial 82 81

2 wkRT 82 82

2 wkHS 82 82,

4 wkRT 83¹ 82²

4 wkHS 81³ 79³

Δ ±1 -2

PH

Initial 9.8 9.3

2 wkRT 9.9 9.3

2 wkHS 9.7 9.2

4 wkRT 9.8 9.2

4 wkHS 9.6 9.0

A -0.2 -0.3

Contrast Ratio

Initial 0.977 0.978

2 wkHS 0.975 0.978

4 wkHS 0.978 0.980

Δ -0.002 + 0.002

Whiteness Index

Initial 78.38 78.75

2 wkHS 78.61 78.61

4 wkHS 77.91 78.07

Δ -0.47 -0.68

Yellowness Index

Initial 3.56 3.43

2 wkHS 3.56 3.57

4 wkHS 3.76 3.72

Δ + 0.20 + 0.29

85° Sheen

Initial 5.2 5.5

2 wkRT 4.7 4.8

2 wkHS 4.8 4.8

4 wkRT 5.5 5.1

4 wkHS 5.5 5.6

Δ -0.5 -0.7

1/8" sep 1/4" sep 1/2" sep

Claims

What is Claimed:

1. A method of pH buffering and reducing the volatile organic content of an air- drying coating formulation con.prising adding an alkoxylated organic amine to said air-drying coating formulation as a pH buffer; applying a coating of said air-drying coating formulation containing the alkoxylated organic amine to a surface under ambient conditions; and allowing said coating to air-dry under ambient conditions, whereby, the alkoxylated organic amine remains in the dried film and thereby reduces the volatile organic content of said air-drying coating formulation.

2. The method of pH buffering and reducing the volatile organic content of an air-drying coating of Claim 1 , wherein said alkoxylated organic amine is prepared by exposing an alkylene oxide to an organic amine having the structure:

I

R i — N— R₃

wherein R_j and R2 are individually a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a straight chain or branched chain alkyl group or aryl group; a methanol group, an ethanol group, a propanol group, a butanol group, or a straight chain or branched chain alcohol group; or an aminomethane group, an aminoethane group, an aminopropane group, an aminobutane group, an aminoalkane group or an aminoaryl group, and R3 is a methanol group, an ethanol group, a propanol group, a butanol group, or a straight chain or branched chain alcohol group; or an aminomethane group, an aminoethane group, an aminopropane group, an aminobutane group, an aminoalkane group, or an aminoaryl group.

3. The method of pH buffering and reducing the volatile organic content of an air-drying coating of Claim 2, wherein said organic amine is selected from the group consisting of diethylaminoethanol, monoethanolamine, monoisopropanolamine, dimethylethanolamine, propanediamine, propylenediamine, diethylenetriamine, and 2-amino-2-methyl-l-propanol. 30

4. The method of Claim 1 wherein said alkoxylated organic amine is ethoxylated.

5. The method of Claim i wherein said alkoxylated organic amine is propoxylated.

6. The method of Claim 1 wherein said alkoxylated organic amine contains an alcohol group.

7. The method of Claim 1 wherein said alkoxylated organic amine is a secondary amine.

8. The method of Claim 1 wherein said alkoxylated organic amine is a tertiary amine.

9. The method of Claim 1 wherein said alkoxylated organic amine has the structure:

R₂

I

R i — N— R₃

wherein R_j is a methyl group, an ethyl group, a propyl group, a butyl group, a straight chain or branched chain alkyl group or aryl group; a methanol group, an ethanol group, a propanol group, a butanol group, or a straight chain or branched chain alcohol group; or an aminomethane group, an aminoethane group, an aminopropane group, an aminobutane group, an aminoalkane group, an aminoaryl group, a combination of the groups thereof with ether linkages therebetween, or a hydrogen atom, R2 is a methyl group, an ethyl group, a propyl group, a butyl group, a straight chain or branched chain alkyl group or aryl group; a methanol group, an ethanol group, a propanol group, a butanol group, or a straight chain or branched chain alcohol group; or an aminomethane group, an aminoethane group, an aminopropane group, an aminobutane group, an aminoalkane group, an aminoaryl group, or a combination of the groups thereof with ether linkages therebetween, and R3 is a methanol group, an ethanol group, a propanol group, a butanol group, or a straight chain or branched chain alcohol group; or an aminomethane group, an aminoethane group, an aminopropane group, an aminobutane group, an aminoalkane group, an aminoaryl group, or a combination of the groups thereof with ether linkages therebetween.

10. The method of Claim 2 wherein said alkylene oxide is ethylene oxide.

11. The method of Claim 2 wherein said alkylene oxide is propylene oxide.

12. The method of pH buffering and reducing the volatile organic content of an air-drying coating of claim 5, wherein said propoxylated organic amine is selected from the group consisting of propoxylated diethylaminoethanol, propoxylated monoethanolamine, propoxylated monoisopropanolamine, propoxylated dimethylethanolamine, propoxylated propanediamine, propoxylated propylenediamine, propoxylated diethylenetriamine, and propoxylated 2-amino-2-methyl-l-propanol.

13. The method of pH buffering and reducing the volatile organic content of an air-drying coating of Claim 12, wherein said propoxylated organic amine is propoxylated 2-amino-2-methyl- 1 -propanol .

14. The method of pH buffering and reducing the volatile organic content of an air-drying coating of Claim 13, wherein said propoxylated 2-amino-2-methyl-l- propanol is prepared by exposing 2-amino-2-methyl-l -propanol to propylene oxide.

15. The method of pH buffering and reducing the volatile organic content of an air-drying coating of Claim 13, wherein said propoxylated 2-amino-2-methyl-l- propanol is prepared by exposing 2-amino-2-methyl-l -propanol to propylene oxide in a molar ratio of about 1:(1-10).

16. The method of pH buffering and reducing the volatile organic content of an air-drying coating of Claim 13, wherein said propoxylated 2-amino-2-methyl-l- propanol is prepared by exposing 2-amino-2-methyl-l -propanol to propylene oxide in a molar ratio of about 1:4.

17. The method of pH buffering and reducing the volatile organic content of an air-drying coating of Claim 13, wherein 100 gallons of said coating comprises from about 1 pound to about 20 pounds of said propoxylated 2-amino-2-methyl-l-propanol.

18. The method of pH buffering and reducing the volatile organic content of an air-drying coating of Claim 6, wherein said ethoxylated organic amine is selected from the group consisting of ethoxylated diethylaminoethanol, ethoxylated monoethanolamine, ethoxylated monoisopropanolamine, ethoxylated dimethylethanolamine, ethoxylated propanediamine, ethoxylated propylenediamine, ethoxylated diethylenetriamine, and ethoxylated 2-amino-2-methyl-l -propanol.

19. The method of pH buffering and reducing the volatile organic content of an air-drying coating of Claim 18, wherein said ethoxylated organic amine is ethoxylated 2-amino-2-methyl-l-propanol.

20. The method of pH buffering and reducing the volatile organic content of an air-drying coating of Claim 19, wherein said ethoxylated 2-amino-2-methyl-l- propanol is prepared by exposing 2-amino-2-methyl-l -propanol to ethylene oxide.

21. The method of pH buffering and reducing the volatile organic content of an air-drying coating of Claim 19, wherein said ethoxylated 2-amino-2-methyl-l- propanol is prepared by exposing 2-amino-2-methyl-l -propanol to ethylene oxide in a molar ratio of about 1:(1-10).

22. The method of pH buffering and reducing the volatile organic content of an air-drying coating of Claim 19, wherein said ethoxylated 2-amino-2-methyl-l- propanol is prepared by exposing 2-amino-2-methyl-l -propanol to ethylene oxide in a molar ratio of about 1:4.

23. The method of pH buffering and reducing the volatile organic content of an air-drying coating of Claim 19, wherein 100 gallons of said coating comprises from about 1 pound to about 20 pounds of said ethoxylated 2-amino-2-methyl-l -propanol.

24. An air-drying coating composition with reduced or low volatile organic content comprising a binder, a solvent and an effective amount of an alkoxylated organic amine to pH buffer the air-drying coating composition, said air-drying coating composition being further defined as a coating that is applied to a structure under ambient conditions and are allowed to air-dry under ambient conditions.

25. The air-drying coating composition with reduced or low volatile organic content of Claim 24, wherein said alkoxylated organic amine is prepared by exposing an alkylene oxide to an organic amine having the structure:

R₂

I

R i — N— R₃ wherein R_j and R2 are individually a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a straight chain or branched chain alkyl group, or aryl group; a methanol group, an ethanol group, a propanol group, a butanol group, or a straight chain or branched chain alcohol group; or an aminomethane group, an aminoethane group, an aminopropane group, an aminobutane group, an aminoalkane group, or an aminoaryl group, and R3 is a methanol group, an ethanol group, a propanol group, a butanol group, or a straight chain or branched chain alcohol group; or an aminomethane group, an aminoethane group, an aminopropane group, an aminobutane group, an aminoalkane group, or an aminoaryl group.

26. The air-drying coating composition with reduced or low volatile organic content of Claim 25, wherein said organic amine is selected from the group consisting of diethylaminoethanol, monoethanolamine, monoisopropanolamine, dimethylethanolamine, propanediamine, propylenediamine, diethylenetriamine, and 2- amino-2-methyl- 1 -propanol .

27. The air-drying coating composition with reduced or low volatile organic content of Claim 24, wherein said ethoxylated organic amine is selected from the group consisting of ethoxylated diethylaminoethanol, ethoxylated monoethanolamine, ethoxylated monoisopropanolamine, ethoxylated dimethylethanolamine, ethoxylated propanediamine, ethoxylated propylenediamine ethoxylated diethylenetriamine and ethoxylated 2-amino-2-methyl-l-propanol.

28. The air-drying coating composition with reduced or low volatile organic content of Claim 27, wherein said ethoxylated organic amine is ethoxylated 2-amino- 2-methyl- 1 -propanol .

29. The air-drying coating composition with reduced or low volatile organic content of Claim 28, wherein said ethoxylated 2-amino-2-methyl-l -propanol is prepared by exposing 2-amino-2-methyl-l -propanol to ethylene oxide.

30. The air-drying coating composition with reduced or low volatile organic content of Claim 28, wherein said ethoxylated 2-amino-2-methyl-l -propanol is prepared by exposing 2-amino-2-methyl-l -propanol to ethylene oxide in a molar ratio of about 1:(1-10).

31. The air-drying coating composition with reduced or low volatile organic content of Claim 28, wherein said ethoxylated 2-amino-2-methyl-l -propanol is prepared by exposing 2-amino-2-methyl-l -propanol to ethylene oxide in a molar ratio of about 1:4.

32. The air-drying coating composition with reduced or low volatile organic content of Claim 28, wherein 100 gallons of said coating comprises between about 1 pound and about 20 pounds of said ethoxylated 2-amino-2-methyl-l -propanol.

33. The air-drying coating composition of Claim 24 wherein said alkoxylated organic amine is ethoxylated.

34. The air-drying coating composition of Claim 24 wherein said alkoxylated organic amine is propoxylated.

35. The air-drying coating composition of Claim 24 wherein said alkoxylated organic amine contains an alcohol group.

36. The air-drying coating composition of Claim 24 wherein said alkoxylated organic amine is a secondary amine.

37. The air-drying coating composition of Claim 24 wherein said alkoxylated organic amine is a tertiary amine.

38. The air-drying coating composition of Claim 24 wherein said alkoxylated organic amine has the structure:

R₂

I

R i — N— R₃

wherein R_j is a methyl group, an ethyl group, a propyl group, a butyl group, a straight chain or branched chain alkyl group or aryl group; a methanol group, an ethanol group, a propanol group, a butanol group, or a straight chain or branched chain alcohol group; or an aminomethane group, an aminoethane group, an aminopropane group, an aminobutane group, an aminoalkane group, an aminoaryl group, a combination of the groups thereof with ether linkages therebetween, or a hydrogen atom, R2 is a methyl group, an ethyl group, a propyl group, a butyl group, a straight chain or branched chain alkyl group or aryl group; a methanol group, an ethanol group, a propanol group, a butanol group, or a straight chain or branched chain alcohol group; or an aminomethane group, an aminoethane group, an aminopropane group, an aminobutane group, an aminoalkane group, an aminoaryl group, or a combination of the groups thereof with ether linkages therebetween, and R3 is a methanol group, an etha ol group, a propanol group, a butanol group, or a straight chain or branched chain alcohol group; or an aminomethane group, an aminoethane group, an aminopropane group, an aminobutane group, an aminoalkane group, an aminoaryl group, or a combination of the groups thereof with ether linkages therebetween.

39. The method of Claim 25 wherein said alkylene oxide is ethylene oxide.

40. The method of Claim 25 wherein said alkylene oxide is propylene oxide.

41. The air-drying coating composition with reduced or low volatile organic content of Claim 34, wherein said propoxylated organic amine is selected from the group consisting of propoxylated diethylaminoethanol, propoxylated monoethanolamine, propoxylated monoisopropanolamine, propoxylated dimethylethanolamine, propoxylated propanediamine, propoxylated propylenediamine, propoxylated diethylenetriamine and propoxylated 2-amino-2-methyl-l -propanol.

42. The air-drying coating composition with reduced or low volatile organic content of Claim 41, wherein said propoxylated organic amine is propoxylated 2- amino-2-methyl- 1 -propanol.

43. The air-drying coating composition with reduced or low volatile organic content of Claim 42, wherein said propoxylated 2-amino-2-methyl-l -propanol is prepared by exposing 2-amino-2-methyl-l -propanol to propylene oxide.

44. The air-drying coating composition with reduced or low volatile organic content of Claim 42, wherein said propoxylated 2-amino-2-methyl-l -propanol is prepared by exposing 2-amino-2-methyl-l -propanol to propylene oxide in a molar ratio of about 1:(1-10).

45. The air-drying coating composition with reduced or low volatile organic content of Claim 42, wherein said propoxylated 2-amino-2-methyl-l -propanol is prepared by exposing 2-amino-2-methyl-l -propanol to propylene oxide in a molar ratio of about 1:4.

46. The air-drying coating composition with reduced or low volatile organic content of Claim 42, wherein 100 gallons of said coating comprises between about 1 pound and about 20 pounds of said propoxylated 2-amino-2-methyl-l -propanol.