Research Institutes of Sweden

A useful tool in substitution

- HSPiP

Martin Andersson

▪ δD – Dispersion

▪ δH – Hydrogen bonding

▪ δP – Polar

Hansen solubility parameters and the Hansen 3D spaceGood solvents

Bad solvents

The software HSPiP is a useful tool

VisualisationOptimisation of solvents and mixtures

Calculation of

evaporation rates

(And very much more…)

Task: To replace xylene in coatings formulations

Initial requirements for a good candidate:

• Close to xylene in Hansen space (7 units distance used)

• Evaporation rate similar to xylene (3 x quicker or slower)

• Low freezing point (melting point lower than 0 deg C)

Dataset of 100 commodity solvents used.

These 10 solvents remained after applying the above requirements:

Sigma-Aldrichwww.thegoodscentscompany.com

0

Additional requirement (environmental)

• Close to xylene in Hansen space (7 units distance used)

• Evaporation rate similar to xylene (3 x quicker or slower)

• Low freezing point (melting point lower than 0 deg C)

• Better environmental and work-environmental profile than xylene (NFPA 704 system used)

NFPA 704: Standard System for the Identification of the Hazards of Materials for Emergency Response

Xylene

Toluene # Ethyl benzene* Cyclopentyl

methyl ether**

*) Wikipedia#) http://cameochemicals.noaa.gov/chemical/4654

**) http://datasheets.scbt.com/sc-252651.pdf

***) http://m.cameochemicals.noaa.gov/chemical/582

****) http://cameochemicals.noaa.gov/chemical/3939

*****) http://cameochemicals.noaa.gov/chemical/11662

******) http://safety.nmsu.edu/programs/chem_safety/NFPA-ratingA-C.htm

Dimethyl-

cyclohexane*** Amyl acetate*

Butyl acetate*

Methyl-

isoamylketone****

Isobutyl-

isobutyrate*****

Iso-Pentyl Acetate*Butyl Propionate******

2

3

0

Xylene*

Amyl acetateMethyl-

isoamylketone****

Isobutyl-

isobutyrate*****Iso-Pentyl Acetate

Lowest price

1L/1Kg*

600 534 3433 776

Odor strength ** Medium No data High High

Odor type** Fruity No data Fruity Fruity

X

*) Sigma-Aldrich (Xylene = 307 SEK/L)

**) www.thegoodscentscompany.com

Amyl acetateMethyl-

isoamylketone****Isobutyl-

isobutyrate*****

Lowest price

1L/1Kg*

600 534 776

Odor strength ** Medium No data High

Odor type** Fruity No data Fruity

*) Sigma-Aldrich (Xylene = 307 SEK/L)

**) www.thegoodscentscompany.com

Methyl

isoamyl

Ketone

Distance: 6.0

Amyl

Acetate

Distance: 5.5

Isobutyl-

isobutyrate

Distance: 6.3

Xylene

Unfortunately all three solvents

are positioned on one side of xylene

- no combination of the solvent gets closer to xylene than 5.5

But how good solvents are these candidates for a typical acrylic polymer?

Paraloid® B-66 (formerly Acryloid B-66)

• Methyl metacrylate and butyl methacrylate copolymer

• Soluble in toluene, xylene, acetone, methyl ethyl ketone and acetone

• Tg = 50 deg C

• Used for paint and clear coatings over wood, plastic and fabric.

• Sold as pellets or as 51% solids solution in toluene or xylene

http://cameo.mfa.org/wiki/Paraloid%C2%AE_B-66

Isobutyl isobutyrate

in Paraloid

B-66 sphere (r= 9)

Methyl isoamyl

ketone

in Paraloid B-66

sphere (r= 9)

Xylene

in Paraloid

B-66 sphere (r= 9)

Amyl acetate

in Paraloid B-66

sphere (r= 9)

307 SEK/L

HSPiP

+Price

Toxicology data

Odor threshold

Odor type

What´s next? Complementary tools!

…and animal free prediction of eye-irritation/swelling of the cornea

Research Institutes of Sweden

THANK YOUMartin Andersson

martin.andersson@ri.se

0768-640025

Conclusions • Hansens solubility parameters and HSPiP software can be useful tools for finding replacement solvents

• These tools, in combination with, price-, environmental-, and odour-data from public sources,

have been used to find a replacement for xylene

• Isobutyl isobutyrate is a promising candidate according to the criteria we have set in the study

• Its classification is:

”Poses no health hazard, no precautions necessary and would offer no hazard

beyond that of ordinary combustible materials (e.g. wood)”

compared to (for xylene)

”Intense or continued but not chronic exposure could cause temporary incapacitation or

possible residual injury (e.g. diethyl ether)”

• Isobutyl isobutyrate has an evaporation rate that is about half of that of xylene

• It has a medium strength fruity odor

• It seems to be in the same price range as xylene

• For the acrylic we examined it seems to be as good a solvent as xylene (right at the border of the

sphere)

• The study should be expanded to include the full set of solvents in HSPiP

• The most promising candidates should be evaluated experimentally in terms of solubility,

function, drying time and odor acceptance etc.

Conclusions