A useful tool in substitution - HSPiP...Conclusions • Hansens solubility parameters and HSPiP...
Transcript of A useful tool in substitution - HSPiP...Conclusions • Hansens solubility parameters and HSPiP...
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
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