Off-Diagonal Effects of Alkanolamines

in Waterborne
Coatings
O
ther than ammonia, alkanolamines convince the reader that Arkema’s Advantex™ addi-
play an important role as the pri- tive is a useful neutralizing alkanolamine alternative
mary evaporative neutralizing for waterborne coatings.
agents used in waterborne coatings.
The adjustment of pH in water- The Off-Diagonal Effect
borne coatings is important in order to maintain a sta- Coating formulations are composed of multiple ingre-
ble pigment dispersion, minimize corrosion, reduce dients added for various reasons. In a typical water-
biological growth and generally optimize the perfor- borne coating, the following generic ingredients may
mance of the coating during storage and application. be present:
After application of the wet coating, the pH-adjusting
agent must, at least partially, evaporate from the film • Solvent: water;
in order to promote the coalescence of the resin • Antifreeze: propylene glycol;
binders via a decrease in pH. • Coalescent: 2,2,4-trimethylpentyl-1,3-pentane-
Alkanolamines are ideal pH-neutralizing agents in a diol monoisobutyrate;
number of ways, including compatibility with latex • Resin: butylacrylate - vinyl acetate
emulsions, solubility in latex emulsions, a sufficiently copolymer;
high pKa value to allow for efficient neutralization to • Pigment: titanium dioxide, other
pH values between 8 and 10, and intermediate vapor inorganic and organic color pig-
pressures that allow for evaporation at a controlled ments and various extenders;
rate. The optimum alkanolamine for a given coating • Surfactant: nonionic surfac-
formulation will be the one with the best balance of tant;
physical properties, allowing for the maximum num- • Dispersant: polyacrylic
ber of benefits and the minimum number of negative acid;
side effects (e.g., odor). • Rheology Modifier: hydrox-
One of the easiest ways to evaluate and compare dif- yethyl cellulose;
ferent alkanolamines as additives in waterborne coat- • pH Adjuster: alkanolamine;
ings is through the concept of off-diagonal effects, and and
this paper will, for clarity, start with a generic descrip- • Biocide: isothiazolinone.
tion of the off-diagonal analysis of additive effects. The
generic discussion will be followed by some physical Each of these ingredients is used
data summaries useful in illustrating how off-diagonal for a reason. The solvent provides a
effects can be predicted ab initio. Ultimately, we hope to vehicle for mixing, as well as a carrier for

By Michael D. Gernon and Conor M. Dowling/Arkema Inc., Philadelphia, PA; and Ben Carlozzo/DCA Coatings, Solon, OH

Reprinted with permission from the April 2006 issue of Paint & Coatings Industry magazine
Off-Diagonal Effects of Alkanolamines in Waterborne Coatings

Table 1/The generic formulation matrix for a waterborne coating. The primary purpose of this paper is to show that
while all alkanolamines exhibit off-diagonal effects,

Emulsion Stability
Resin Coalescence
Freeze Stability both positive and negative, only certain alka-
nolamines are exceptional with respect to their ability

Biostability
to improve latex paint through significant positive

Dispersion
Additive

impacts on odor, corrosion properties, adhesion,

Effect

Binding
Mixing

Color
biostability, pigment stability, coalescence and overall

Flow

pH
performance. What follows is a comparative summary
Solvent  +/- +/- +/- +/- +/- +/- +/- +/- +/- of the physical and chemical properties of several
Antifreeze +/-  +/- +/- +/- +/- +/- +/- +/- +/- alkanolamines used in latex paint, with an emphasis
Coalescent +/- +/-  +/- +/- +/- +/- +/- +/- +/- on how these properties impact paint performance.
Resin +/- +/- +/-  +/- +/- +/- +/- +/- +/-
Pigment +/- +/- +/- +/-  +/- +/- +/- +/- +/- Off-Diagonal Effects in Action
Surfactant +/- +/- +/- +/- +/-  +/- +/- +/- +/-
Dispersant +/- +/- +/- +/- +/- +/-  +/- +/- +/- Vapor Pressure
Rheology +/- +/- +/- +/- +/- +/- +/-  +/- +/- The vapor pressure of a material can have conse-
Alkanolamine +/- +/- +/- +/- +/- +/- +/- +/-  +/- quences in a liquid paint as well as in a dried coating.
Biocide +/- +/- +/- +/- +/- +/- +/- +/- +/-  With respect to the alkanolamine, any unpleasant
odor associated with this additive will be enhanced by
the other ingredients. The antifreeze stabilizes the its volatility, and the volatility of an alkanolamine is a
mixture, allowing freeze/thaw cycling. The coalescent direct function of its vapor pressure. During the dry-
improves the physical properties of the dried binder by ing stage of a waterborne coating, a controlled volatil-
permitting the formation of a continuous film. The ity can also promote better film formation. As is usu-
resin, which becomes the actual film, also acts as a ally the case, a balance of properties is needed to
binder for the pigment and other non-volatile compo- optimize coating performance.
nents of the paint. The pigment provides for color, The vapor pressure of an alkanolamine can be
opacity and reinforcement. The dispersant allows for described by a number of equations, including the
-A
proper pigment dispersion during the grind and for Clausius-Clapeyron equation ln(P) = T +B, the
-A
stabilization of pigment-binder interactions in the fin- Antoine equation ln(P) = T-C +B, and the Riedel
-A
ished liquid paint. The rheology modifier adjusts the equation ln(P) = T +B+Clog(T)+DT E
viscosity of the coating, allowing for the appropriate wherein A,B,C,D and E are regarded as
flow properties and smooth application. The alka- correlation constants, P = vapor pres-
nolamine is used to adjust the pH to an optimal point, sure of the pure liquid, and T =
and the biocide is used to extend the shelf stability of absolute temperature. The con-
the product by guarding against biological attack. stants can be determined
Each of these primary purposes can be thought of as empirically by best-fitting
the diagonal effects of the ingredients. pressure-temperature data
The 10 x 10 matrix shown in Table 1 can be used to from vacuum distilla-
represent the effects of the individual additives on the tions. The Clausius-
coating formulation. The primary (diagonal) effects of Clapeyron equation is
the additives are represented by checks along the diag- sufficient to provide a
onal. The off-diagonal effects of the additives are given good estimate of vapor
as a +/- symbol in all of the off-diagonal positions. pressure behavior
These +/- symbols represent the potential positive or between 20 and 150 ºC.
negative contributions that each additive can have on Correlation constants for
all the properties of the coating for which it was not five alkanolamines com-
primarily added. For instance, certain readily biode- monly used in waterborne
graded resin binders will have a negative impact on coatings are given in Table 2.
the biostability of the coating during storage (so-called Using the Clausius-Clapeyron
‘in-can’ stability). Many organic solvents have a posi- equation, one can equate the
tive effect on the freeze stability and resin coalescence constant A with the enthalpy of
properties of a given coating formulation. It is only vaporization divided by the universal
through maximum enhancement of the off-diagonal gas constant R (8.31447 J/ºK-mole) and the
effects in a given coating that a truly optimal formula constant B with the entropy of vaporization divided by
can be found. the universal gas constant.
Off-Diagonal Effects of Alkanolamines in Waterborne Coatings

Table 2/Vapor pressure data calculated from empirical Clausius-Clapeyron calculations of HLB values have been developed. One
correlation for five alkanolamines used in waterborne coatings (see supple- useful method involves taking the percentage of the
mental materials section). molecule’s overall MW that can be identified as
Enthalpy of Entropy of Vapor Vapor hydrophilic and dividing it by 5.1 This method was
Alkanolamine Vaporization Vaporization Pressure Pressure applied to a number of alkanolamines commonly
KJ/mol J/K-mol (Torr) @ 20 ºC (Torr) @ 100 ºC employed in waterborne coatings (MW of
Advantex™ 55.7 172.3 0.1 16 hydrophilic portion of the molecule taken as 60)
AMP-95® 54.48 179.9 0.5 59 along with a reference number for a pure alkane to
Monoethanolamine 56.05 181.54 0.3 50
Triethanolamine 82.29 192.5 0.00002 0.034 yield the values shown in Table 3.
The differences in calculated HLB values for differ-
Table 3/HLB value approximations. ent alkanolamines, as given here, are manifested in
the real world as subtle differences in the surfactant-
Alkanolamine HLB like behavior of the alkanolamines. Figure 1 shows a
MEA (monoethanolamine) 20 semi-log presentation of surface tension (dynes/cm,
TEA (triethanolamine) 20
MAE (methylaminoethanol) 16 aqueous solution – air) versus concentration
AMP 13 (mmol/liter) data collected at room temperature
Advantex™ additive 10 (22 ºC) and standard pressure (1 atm). The surface
Alkane 0 tensions were measured by the maximum bubble pres-
sure method with automatic hydrostatic pressure cor-
Figure1/Air-solution surface tensions of aqueous solutions of two alka- rection on a SITA® T-60 unit. Advantex™ additive
nolamines as a function of concentration. Semi-log plot of data collected by shows an apparent critical micelle concentration
maximum bubble pressure method on a SITA T-60 unit with automatic (CMC) of approximately 1M, while AMP, with a higher
hydrostatic pressure correction at a bubble rate of 1 sec-1. calculated HLB, shows an almost continuous varia-
tion in surface tension from a concentration of 10
Surface Tension (dynes/cm)

80
70 mmol all the way up to 50% wt/wt. The subtle surfac-
60 tant-like behavior of Advantex™ has real benefits
50 with respect to pigment surface wetting, pigment dis-
40 persant activity, film forming, corrosion inhibition
30 Advantex™ and emulsion stability.
20 AMP One practical manifestation of HLB is in corrosion
10 protection. Materials with lower HLB values tend to
0
form better corrosion barriers on metal surfaces. To
1 10 100 1000 10000
illustrate this, we ran the following experiment. Brass
Concentration (mmol/liter)
(2” x 2” x 0.032”) panels were immersed in aqueous
solutions of alkanolamine (0.3 M) and octanoic acid
Triethanolamine has a very low vapor pressure (0.2 M) and adjusted with H3PO4 and/or KOH to pH
and correspondingly low odor, but evaporation of equal to 8.5 at room temperature. A 450-gram por-
triethanolamine from coatings is extremely slow. tion of leach solution was weighed carefully and trans-
AMP and MEA have adequate volatility for evapora- ferred to a wide-mouth screw-cap glass bottle. The
tion, but these amines produce sufficient vapor pres- brass panels were washed with 10% Liqui-Nox®
sure to create noticeable odor. The vapor pressure of cleaner and buffed dry with a paper towel. The panels
Advantex™ additive is an excellent compromise that were immersed in the various solutions (all panels ori-
allows for evaporation while still producing a very ented at the same angle within the solution) and the
low overall odor. cap placed tightly on the jar. A 5-gram sample of each
solution was collected at regular intervals and ana-
HLB lyzed by ICP/emission for metals content. In this
The HLB (hydrophile-lipophile balance) of a surfac- graph, the 30-day concentrations are reported. The
tant molecule is a measure of the balance of brass alloys were leaded (CA-360, 3% Pb) and
hydrophilic (water loving) and lipophilic (oil loving) unleaded (CA-260) alloy. HLB values: Advantex™
properties of the molecule. Originally, HLB values additive = 10 (Cu concentration = 9 ppm for both
were measured experimentally by determining leaded and unleaded), AMP = 13 (Cu concentration =
which of a number of standard oil-water emulsion 74 ppm for leaded and 123 ppm for unleaded), MEA =
mixtures a given surfactant was capable of emulsify- 20 (Cu concentration = 134 ppm for leaded and 211
ing. More recently, a number of useful approximate ppm for unleaded), DGA = 20 (Cu concentration =
Off-Diagonal Effects of Alkanolamines in Waterborne Coatings

molecule that provides excellent corrosion inhibition,

Figure 2/Copper leaching from alkanolamine neutralized aqueous solu-
emulsification assistance, pigment wetting, leveling
tions.
assistance, etc., while still being high enough to allow
250
Unleaded Brass for complete solubility in and compatibility with a
[Cu], ppm

200
150 Leaded Brass waterborne coating formulation.
100
50 pKa
0 The pKa of an alkanolamine can be conveniently
9 11 13 15 17 19
measured by a careful pH titration of highly purified
HLB
alkanolamine with degassed standard acid solution.
Table 4/The pKa of some alkanolamines measured as the pH at 1/2 neu- Based on the Henderson-Hasselbach equation:
tralization. AMP-95 compound is 2-amino-2-methyl-1-propanol. TEA is tri- pKa = pH – log [R3N]/[R3NH+], the pH at 1/2 neutral-
ethanolamine; MAE is methylaminoethanol; and MEA is monoethanolamine. ization will be equal to the pKa. The pKas of a number
Alkanolamine pKa taken as pH at 1/2 neutralization of purified alkanolamines determined by pH titration
Advantex™ additive 10.04 of the free base with nitric acid are given in Table 4.
AMP-95 9.88 The pKa of the alkanolamine used in a waterborne
TEA 7.76 coating has an influence on the performance of the
MAE 9.98 coating. Higher pKa alkanolamines allow for more
MEA 9.50
efficient neutralization and higher working pH levels,
while lower pKa alkanolamines have some utility as
reserve alkalinity in open industrial systems. The pKa
Figure 3/Plot of “Maximum Growth Slope” of Pseudomonas aeruginosa
of Advantex™ is high enough to allow for very effi-
(ATCC 10145) in transparent TSB media buffered to pH 8.5 with trihydroxy-
methyl-methylamine (Tris) as a function of the concentration of 20% BIT sus- cient neutralization coupled with some reserve alka-
pension. The lower growth observed in the system containing Advantex™ is linity. Overall, Advantex™ has an excellent pKa for
indicative of greater biocide efficacy in this case. latex paints and waterborne coatings.
0.4
Biocide Synergy
0.35
The best way to prevent the microbial colonization of
Best Fit Growth Slope

0.3 paint is to add biocide. Many classes of biocides are

(milliOD/min)

0.25 known, and many measurements of the Minimum

0.2 AMP (2000 ppm) Inhibitory Concentrations (MIC = the minimum con-
0.15 centration of the biocide necessary for control of a
Advantex™ (2000 ppm)
particular species of bacteria or fungi) of these differ-
0.1
ent biocides have been made. However, toxicology, reg-
0.05
ulatory, economic and chemical stability issues com-
0 plicate the otherwise straightforward strategy of
500 ppm 250 ppm 150 ppm 50 ppm adding a biocide to a commercial product. So whereas
[BIT as 20% suspension], pH = 8.5 the use of biocides is nearly universal, the minimiza-
tion of biocide concentrations is sought.
How can the formulator deal with the contradic-
168 ppm for leaded and 234 ppm for unleaded), and tory goals of absolute biological control and mini-
TEA = 20 (Cu concentration = 165 ppm for leaded and mization of biocide concentrations? One possible
171 ppm for unleaded). The passive corrosion rates for approach is the use of biocide synergy. Biocide syn-
brass panels immersed in neutralized aqueous solu- ergy is a term used to describe the favorable effect of
tions, as described above, are plotted versus the HLB of certain “non-biocidal” additives on the overall bio-
the alkanolamine-neutralizing agent in Figure 2. logical stability of a fluid.2,3 Biocide synergy is an off-
One might surmise that the lowest possible HLB diagonal effect that was first reported for alka-
would be ideal for optimization of corrosion inhibi- nolamines by Ed Bennett in 1979,4 and that biocide
tion, but HLB values much lower than 10 lead to insol- synergy is one of the best-researched examples of an
ubility in aqueous media. Thus, it can be seen that off-diagonal effect of an additive.5-7
Advantex™ additive has balanced properties that One of Arkema’s contributions to general work in
allow for optimal performance (e.g., good corrosion this field has been the development, in collaboration
inhibition and aqueous solubility) in waterborne coat- with Microbe Inotech Laboratories (MIL, Saint Louis,
ings. The calculated HLB value of 10 is indicative of a MO), of standardized methods for the comparison of
Off-Diagonal Effects of Alkanolamines in Waterborne Coatings

Table 5/Generic grind paste for a semi-gloss formulation. of the wells. Typically, at least three replicates of each
solution are used to ensure that statistical abnormalities
Material Name Pounds Gallons PVC
did not influence the data. The maximum growth slope
GRIND PASTE
is calculated by computer analysis of 15 data point
Water 34.33 4.12
Freeze/thaw additive 34.55 3.99 sequences from the beginning to the end of the experi-
Defoamer 1.00 0.12 ment. The greatest slope found is taken as the maximum
Alkanolamine 4.00 0.54 growth slope (MGS). The r2 value is checked to ensure
Dispersant 6.00 0.62 that the slope value came from a reasonably linear por-
Non-ionic surfactant 2.00 0.23
tion of the data. The data can be fit to a partial log model,
Titanium dioxide 253.50 7.61 20.00
Extender pigment 24.94 1.15 3.02 but such conversion is not necessary for quantification
Total 360.32 18.38 of relative maximum growth rates. Once an accurate
MGS is determined, it can be plotted versus the concen-
Table 6/Amount of excess pigment that could be added to a modified tration of various additives present in the different
paint formulation containing no pigment dispersant. growth media. Through an examination of MGS values
for different alkanolamines in otherwise identical solu-
Alkanolamine Additional Pigment Allowed
tions, an assessment of relative biocide synergy can be
Advantex™ 71%
AMP-95 43% made. A typical graph of “Maximum Growth Slope” ver-
MAE 50% sus the concentration of the biocide benzoisothiazoli-
MEA 0% none (BIT) is given in Figure 3.
It is clear from the results in Figure 3 that Advan-
Table 7/Possible positive, neutral and negative effects of an alkanolamine tex™ is an excellent biocide synergist, and these
in a paint formulation. A large positive sign indicates a strongly favorable results are completely typical of that seen in the lit-
effect. A regular size plus sign indicates a mildly positive effect. An NE indi- erature and throughout the extensive testing we
cates no effect. A regular size negative symbol indicates a mildly negative
have completed. Alkanolamines like tri-
effect, and a large negative symbol indicates a strongly negative effect.
ethanolamine (TEA) exhibit next to no biocide syn-
Pigment Suspension

ergy. Alkanolamines like DGA and MEA exhibit min-

Color Development

Emulsion Stability
Resin Coalescence

imal biocide synergy. Alkanolamines like AMP

Freeze Stability

exhibit moderate biocide synergy, while alka-

Biostability

nolamines like Advantex™ exhibit the highest level

Effect
Additive

of biocide synergy obtainable in a commercially

Odor

available product. The impact of biocide synergy on

pH

the formulation strategy of a paint maker is less sig-

Advantex™ + + + NE + +  + nificant than it is in other areas like, for instance,
AMP-95 - NE NE NE + +  + metalworking fluids, but the effect can still be used to
MEA - NE NE NE NE NE  NE
TEA + + NE - NE NE  NE advantage in paints and waterborne coatings in gen-
eral.
various alkanolamines as biocide synergists. We have
used high-throughput optical absorbance measure- Pigment Dispersion
ments of bacterial growth in transparent broth media The physical properties of an additive result in unique
to compare various alkanolamines as synergists. In behavior within a formulation. One of the more
brief, the Arkema/MIL method involves dosing an important side effects of paint additives is their posi-
appropriate pH-buffered transparent broth with various tive or negative influence on pigment dispersion.
levels of biocide (e.g., triazine, BIT, CMIT/MIT) and Generally, there are optimal levels of dispersant and
alkanolamine. The prepared broths are dosed into the liquid required to give different types of pigment the
wells of a microtiter plate followed by standardized inoc- best grind viscosity. These levels are based on the oil
ulation of all wells with a bacterial suspension of absorption of the pigments in the grind. The morphol-
approximately 1010 CFU/ml (≈ 108 CFU/ml after dilu- ogy of the pigments is also important, since the major
tion). The prepared microtiter plate is placed in a tem- role of dispersant is to act as a bridge between pigment
perature-controlled instrument chamber (typical inoc- particle and liquid carrier, displacing air from the pig-
ulation T = 25 ºC), and absorbance measurements at ment surface, and facilitating the breakdown of
660 nm are made on all wells once every 15 minutes. agglomerated pigment. Generally the dispersant pre-
The incubation is allowed to continue for two days. sent in a latex paint is either a sodium, potassium or
After two or more days, the absorbance data is ana- ammonium salt of a polycarboxylic acid. As our work
lyzed to determine how rapidly the bacteria grew in each on HLB has shown, alkanolamines do have surface-
Off-Diagonal Effects of Alkanolamines in Waterborne Coatings

assistance to the dispersion process, and one could

infer from the results that Advantex™ is an excep-
tional “pigment dispersant synergist”.

Conclusions
Just how much does the alkanolamine matter in a
paint formulation? Let’s reexamine a modified off-
diagonal effect matrix with respect to the alka-
nolamine as given in Table 7. The alkanolamine may,
in addition to changing the pH, have an impact on the
odor, color development, freeze stability, coalescence
(particularly in low-VOC formulations), emulsion sta-
bility, pigment suspension stability and biostability of
the paint. Table 7 illustrates the average impact of sev-
eral alkanolamines on the typical flat and semi-gloss
formulations we examined.
The impact of the alkanolamine on freeze stability is
through modified emulsification, which is in turn a
active properties. Although they are relatively small function of HLB — not necessarily the highest or lowest
molecules compared to typical commercial dispersants, HLB, but the best balanced HLB for the system under
it is obvious that they can help in the role of dispersant. consideration. The impact of the alkanolamine on resin
We have established “pigment dispersant synergy” coalescence is through vapor pressure — again, not
with a number of experiments. In one simple experi- necessarily the highest or lowest VP, but the best bal-
ment, several alkanolamines were tested to evaluate anced VP for the system under consideration. The
their dispersant characteristics. The alkanolamines impact of the alkanolamine on pigment suspension sta-
studied included Advantex™, AMP-95, bility and biostability is a complex function of molecu-
monoethanolamine (MEA) and methylaminoethanol lar structure, but again the best effect is obtained
(MAE). This grind paste from a typical semi-gloss paint through an ideal balance. In our testing, Advantex™
was modeled with TiO2 and sodium potassium alu- demonstrated an excellent balance of physical proper-
mino-silicate (Minex 4) as the pigments, with their ties that make it effective as not only a pH-neutralizing
levels appropriate for a 40 NVV-24 PVC system. The agent but also as an optimal off-diagonal synergist. 
base paint formulation employed 4 pounds/100 gal-
lons of amine and 6 pounds/100 gallons of disper- References
sant. The generic grind paste from that semi-gloss for- 1 Griffin, W. C. J. Soc. Cosmetic Chemists 1954, 5(4), 249-256.
mulation is shown in Table 5. 2 Gernon, M. D.; Hemming, B. C. Lubes’N’Greases 2005, 11(5), 18-24.
The experiment involved replacement of all the 3 Gernon, M. D. Tribology & Lubrication Technology 2005, 61(11), 38-40.
dispersant with an equivalent amount (wt/wt, 6 4 Bennett, E. O. Lubr. Eng. 1979, 35(3), 137-144.
pounds per 100 gallons) of alkanolamine followed 5 Sandin, M.; Allenmark, S.; Edebo, L. Biomedical Letters 1992, 47, 85-
by evaluation of the amount of additional pigment 92.
that could be successfully added to the grind without 6 Bazylak, G.; Aboul-Enein, H. Y. Saudi Journ. Pharm. Research 2000,
binding, excess strain and heating. The end point 8(4), 145-163.
was approximate but quite obvious, as the addition 7 Aumann, U.; Brutto, P.; Eachus, A. Lubes’N’Greases 2000, 6(6), 22-26.
of too much pigment, without added commercial
dispersant, would lead to an extremely hard grind For further information contact Michael D. Gernon, Arkema Inc., 610/878.6681,
mass in the disperser with significant stain and [Link]@[Link]; Conor M. Dowling, Arkema Inc.,
excess heat generation. Table 6 presents the results 215/419.7465, [Link]@[Link]; or Ben Carlozzo, DCA Coatings,
of the experiment. Advantex™ gave the greatest 440/221.4265, Bcarlozzo@[Link].
Off-Diagonal Effects of Alkanolamines in Waterborne Coatings

Appendix
Raw Data for approximate Vapor Pressure Calculations

Advantex™ (GMW = 117.19) additive:

BP (oC) BP (K) P (torr) P (KPa) Advantex™ is a trademark belonging to Arkema Inc.
204 477.15 760 101.32 AMP-95® is a registered trademark belonging to
200 473.15 756 100.79 Angus Chemical Company.
96 369.15 13 1.733 SITA® is a registered trademark belonging to SITA Corporation
92 365.15 11 1.466 Liqui-Nox® is a registered trademark belonging to Alconox, Inc.

AMP (GMW = 89.14, CAS RN 124-68-5):

BP (oC) BP P P (KPa) Reference
(K) (torr)
164 437.15 760 101.323 Jedlinski, Z.; Paprotny, J.; [Link]., 1966, 40, 1487-1493.
102 375.15 64 8.532 Johnson; Degering; [Link]., 1943, 8, 11.
88 361.15 39 5.199 Naesaenen; Lindell; Finn. Chem. Lett., 1975, 38.
75 348.15 16 2.133 Di Giorgio; Sommer; Whitmore; [Link]., 1949, 71, 3255.
68 341.15 10 1.333 Adkins; Billica; [Link]., 1948, 70, 3121.
56 329.15 6 0.800 Mathis et al., Bull. Soc. Chim. Fr., 1970, 3047 – 3055.

MEA (GMW = 61.08, CAS RN 141-43-5):

P BP Reference
(Torr) (K)
Touhara, H.; Okazaki, S.; Okino, F.; Tanaka, H.; Ikari, K.; Nakanishi, K.; J. Chem.
0.5 298.15
Thermodynamics 1982, 14(2), 145-156.
11 357.15 Alner et al.; J. Chem. Soc. A 1968, 417-420.
37 363.15 Mathis et al.; Bull. Soc. Chim. Fr. 1970; 3047-3055.

79 383.15 Pividal, K. A.; Sandler, S. I.; J. Chem. Eng. Data 1990, 35 (1), 53-60.

760 443.15 Stone, P. G.; Cohen, S. G.; J. Amer. Chem. Soc. 1982, 104(12), 3435-3440.

TEA (GMW = 149.19, CAS RN 102-71-6);

BP P
BP (oC) P (KPa) Reference
(K) (torr)
176 449.15 2 0.26664 Bhattacharyya; Nakhate; [Link] [Link]., 1947; 24, 7.
194 467.15 10 1.3332 Germann; Knight; [Link]., 1933, 55, 4150.
206 479.15 15 1.9998 Jones; Burns; [Link]., 1925, 47, 2971.
Suzuki et al.; Kogyo Kagaku Zasshi, 1969; 72, 720; [Link].;
278 551.15 155 20.6646
72; 33224; 1970.