L A M B I O T T E & C I E S . A .

Acetals
in Coatings, Inks
and Adhesives

&Cie
 I. S O LV E NT POW E R

The Kauri-Butanol is an international, standardized measure of solvent power, and is governed by an ASTM standardized test, ASTM
D1133. The result of this test is a scaleless index, usually referred to as the “Kb value”. A higher Kb value means the solvent is more
aggressive or active in the ability to dissolve certain materials.

Kb
200 200 200
200

164 164

150
136

120

105
94 95
100

75

51
50
30 33
28

The solubilization even in high amounts of different types of resins and polymers, including polyurethanes and epoxies, can be achieved
with acetals. In the formulation of paints, graffiti and adhesive removers, dichloromethane or N-Methyl Pyrrolidone can be substituted
by Methylal, Dioxolane or TOU.

II. O R G ANI C SOLVE NT S M I SCI BILITY

Acetals are miscible with all organic solvents. This feature allows working on tailored solvent/co-solvent systems to reach specific
properties (solvency, evaporation rate, etc…).

III. WATE R M I SCI B I L I T Y

Acetals are miscible with water to various extents and therefore act as co-solvents in waterborne systems. Acetals that are partly miscible
with water become fully miscible in presence of an alcohol.

Acetal Acetal solubility in water (g/l) Water solubility in acetal (%)

Methylal 330 4
Ethylal 70 1.21
Propylal 3.65 0.45
Butylal 0.22 0.24
TOU Fully miscible Fully miscible
2-Ethylhexylal Not miscible Not miscible
1,3-Dioxolane Fully miscible Fully miscible

2 L A M B I O T T E & C I E S. A.
I V. W E T T IN G E N H ANCE M E NT

Thanks to their low surface tension, acetals can enhance the wetting ability of coatings and inks; this can be highly beneficial in the case
of application on substrates of low energy surface such as plastics, where additives typically are required.

Surface tension
(mN/m)
50

44.6
42.9
40.9
40
36.8
35.6 36
34.3

31.5
30
27.7 27.9
26.7
24.6 24.8 25.2 25.2
24.5
23 23.2 23.3 23.4
21.6 22
21.2
20

10

Methylal and Ethylal can significantly enhance the wetting ability of water-based systems. While Methylal slightly outperforms IPA at
same ratio, a 5% Ethylal solution into water is found to have a surface tension value equivalent to a 20% Ethanol solution.

Surface tension
(mN/m)
80
72.26
Ethanol
70
Methylal

Ethylal
60
IPA

50

40
33.38
36.4

30
27.84

25.73
20
0 5 10 15 20 25 30 35

% solution in water

L A M B I O T T E & C I E S. A. 3
 V. E VA P OR AT I ON R AT E

Another key feature of acetals is their evaporation rate, as they can considerably positively impact the drying time of the coating or the ink.

Evaporation rate Evaporation rate

Acetal
(Diethyl ether = 1) (Butyl acetate = 1)
Methylal 1.36 0.11
Ethylal 3.0 0.25
Propylal 14.0 1.25
Butylal Not available 5.54
TOU Not available 17.38
2-Ethylhexylal No evaporation No evaporation
1,3-Dioxolane 3.6 0.29

The drying time of waterborne systems can also be dramatically decreased in presence of acetals like Methylal, Ethylal or Dioxolane,
compared to Ethanol, Ethylal Acetate, etc….

Evaporation rate
(Diethyl ether=1)

0
Ethanol 100% Water 20% Water 20% Water 14,93% Ethylal 100%
Ethanol 80% Ethylal 40% Ethylal 62,38%
Ethanol 40 % Ethanol 22,68%

In aerosol and spray applications, Methylal is reducing significantly the drying time of hydro alcoholic mixtures.
Below, formulations propelled with DME :

Evaporation
time (s)

120

100

80

60

40

20

0
Water 20% Water 20% Water 20%
Methylal 0% Methylal 20% Methylal 40%
Ethanol 50% Ethanol 30% Ethanol 10%
DME 30% DME 30% DME 30%

4 L A M B I O T T E & C I E S. A.
V I . V I S C O S IT Y

Acetals exhibit a range of low to very low viscosity values. The lowest viscosities are ideal for deep penetration into porous substrates;
they also enable low shear during application by spray. If used as co-solvent they may help tailoring the rheology of the system.

mPa.s
2.50
2.42

2.14
2.04
2.00

1.70
1.66

1.52
1.50
1.26

1.06
1.00
0.79
0.73
0.64
0.56 0.59
0.50
0.41 0.42 0.45
0.40
0.32 0.32

0.00

Measures at 25°C except (*) at 20°C

Source: European Chemical Agency website

Once in water, acetals such as Methylal and Ethylal are known to increase the viscosity of the solution; this effect might lead to a lower
need of rheological additive.

V I I . S U S TA IN A B ILI T Y

B i o s o u rc i ng
• Ethylal is produced from bio-ethanol
• Other acetals can potentially be manufactured from bio-alcohols

L o w e c o - t oxi ci ty
• Acetals have low to no eco-toxicological labeling
• In Germany, acetals listed under the terms of the Federal Water Act on the Classification of Substances Hazardous
to Water in Water Hazard Classes (VwVwS), are assigned WGK 1 - low water hazard

L A M B I O T T E & C I E S. A. 5
 V III. S A FE T Y, L AB E L I NG AND R EGULATORY COMPLIANCE

Further to the adoption of the “Globally Harmonized System of Classification and Labelling of Chemicals (GHS)” by many countries around the
world these last years, substances traditionally used in the Coatings, Inks and Adhesives industries are progressively heavily re-classified
and consequently subject to limitation or restriction.

Many mixtures containing these substances now see their labeling negatively impacted and are in need of reformulation in order to comply
with local regulations and/or consumer products standard criteria (Ecolabel,…). Although alternatives to these substances of concern
are identified, some are not appreciated because of the drowsiness and dizziness effects they can cause to operators and/or end users,
while the use of others is limited by indoor VOC emissions standards.

Under the terms of CLP in Europe or GHS in the rest of the world, acetals are granted exceptionally low toxicological and eco-toxicological
labeling, and therefore are ideal candidates for substituting a wide range of hazardous components, such as:

Effects on Central
Carcinogenic, Mutagenic Other
Nervous System/
and Reprotoxic hazards hazards
Narcotic hazard
Trichlorethylene Ethyl acetate d-Limonene
Perchlorethylene Butyl acetate Xylene
Methylene chloride Isohexane …
N-Methyl Pyrrolidone (NMP) White spirit
N-Ethyl Pyrrolidone (NEP) Methyl Ethyl Ketone (MEK)
Tetrahydrofurane (THF) Isopropyl Alcohol (IPA)
Dimethylformamide (DMF) Acetone
Toluene Heptane
… …
Source: European Chemical Agency website

Volatile Organic Compou n d em issio n s

2-Ethylhexylal is non-VOC under the terms of the following regulations:
• European Directive 1999/13/EC (Vapor pressure < 0.01kPa at 293.15K)
• European Directive 2004/42/CE (Boiling Point > 250°C at 101.3kPa)

Methylal and Dioxolane have Maximum Incremental Reactivity (MIR) values listed under:
• Title 17, California Code of Regulations, Article 1, Tables of Maximum Incremental Reactivity Values,
Section 94700

Food contact
• Dioxolane is listed on COMMISSION REGULATION (EU) No 10/2011 on plastic materials and articles intended to
come into contact with food
• Dioxolane, Ethylal and TOU are listed either on Annex I or Annex 6 of the Swiss Ordinance SR 817.023.21 on
Materials and Articles in Contact with Food
• Methylal and Butylal appear on the Combined Positive List Of Organic Substances in Contact with Drinking Water
of the 4MS Group (France, Germany, the Netherlands and the United Kingdom)

6 L A M B I O T T E & C I E S. A.
 A p p li cat i ons

Paint & Graffiti Removers

Inks
Spray A
dhesive
s

PVC A
dhesiv
Aerosol Paints es

esives
PU Adh

Heat
-sea
lable
Adhe
sives

s Paints
Shrink Sleeve

LL AA M
M BB II OO TT TT EE && CC II EE S. A.
S. A. 7
 &Cie

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