HSP Application note #43
Hydrogen Bonding Donor and Acceptor2010.7.15
HSPiP Team Senior Developer, Dr. Hiroshi Yamamoto
We begin to start hydrogen bonding term(dH term) divided into donor and acceptor.
Hansen Solubility Parameters (HSP)Hansen Solubility Parameters(HSP) were developed by Charles M. Hansen as a way of predicting if one material will dissolve in another and form a solution. They are based on the idea that "like dissolves like" where one molecule is defined as being 'like' another if it bonds to itself in a similar way. What can perhaps be surprising is that one can assign HSP to so many different things. Gases like carbon dioxide, solids like carbon-60, sugar, and biological materials like human skin, depot fat, DNA, and even some proteins all have HSP. The list can be continued with drugs, polymers, plasticizers, and in fact any organic material and even many inorganic materials like salts. The only requirement for an experimental confirmation is that the material must behave differently in a sufficient number of test solvents upon contact. Pirika JAVA Demo Applet calculate HSP. HSPLight is available here. |
We spend a lot of time to build new HSP distance and HSP similarity scheme.
But we need further study.
The first scheme, the total heat of vaporization should be identical.
dH2=dHdo2+dHac2 Scheme (1)
dHdo:donor term
dHac:acceptor term
And for the ratio of donor/acceptor, we apply Prof. Abraham, UCL (University College London) Abraham-D and Abraham-A.
dHdo:dHac=Abraham-D:Abraham-A Scheme (2)
So, we made the algorithm to determine dHdo, dHac that satisfy scheme(1) and(2).
And implement it into Y-MB.
We get dHdo, dHac for every compounds (thanks to prof. Abraham) but we just start research to find relationship solubility and dHdo, dHac.
The biggest problem is cross term.
Donor compounds will interact Acceptor very strongly.
So cross term decrease HSP distance. But how much this cross term decrease HSP distance.
HSP DistanceTo calculate the distance (Ra) between Hansen parameters in Hansen space the following formula is used: HSP distance(Ra)={4*(dD1-dD2)2 + (dP1-dP2)2 +(dH1-dH2)2 }0.5 |
Still we need researching.
We try to analyze the polymer for packing HSP with dHdo, dHac.
We apply SOM analysis and found that the strongly swelling solvents are divided into 2 groups.
But there is no significant difference from the point of dHdo, dHac.
Hcode | name | dD | dP | dH | dHdo | dHac | Vol |
6 | acetic anhydride | 16 | 11.7 | 10.2 | 0.00 | 10.20 | 95 |
7 | acetone | 15.5 | 10.4 | 7 | 0.12 | 7.00 | 73.8 |
11 | acetophenone | 18.8 | 10 | 4 | 0.10 | 4.00 | 117.4 |
17 | acetylacetone | 16.1 | 10 | 6.2 | 0.09 | 6.20 | 103.1 |
25 | acrylonitrile | 16 | 12.8 | 6.8 | 0.84 | 6.75 | 66.2 |
46 | aniline | 20.1 | 5.8 | 11.2 | 5.97 | 9.48 | 91.6 |
52 | benzene | 18.4 | 0 | 2 | 0.00 | 2.00 | 89.5 |
115 | gamma-butyrolactone | 18 | 16.6 | 7.4 | 0.10 | 7.40 | 76.5 |
122 | carbon tetrachloride | 17.8 | 0 | 0.6 | 0.60 | 0.00 | 97.1 |
156 | chloroform | 17.8 | 3.1 | 5.7 | 5.70 | 0.03 | 80.5 |
181 | cyclohexane | 16.8 | 0 | 0.2 | 0.00 | 0.20 | 108.9 |
182 | cyclohexanol | 17.4 | 4.1 | 13.5 | 7.17 | 11.44 | 105.7 |
195 | trans-decahydronaphthalene | 18 | 0 | 0 | 0.00 | 0.00 | 159.3 |
209 | diacetone alcohol | 15.8 | 8.2 | 10.8 | 3.00 | 10.37 | 124.3 |
254 | diethyl carbonate | 15.1 | 6.3 | 3.5 | 0.00 | 3.50 | 121.7 |
270 | 2-(2-methoxyethoxy)ethanol | 16.2 | 7.8 | 12.6 | 3.27 | 12.17 | 118.2 |
285 | N,N'-dimethylacetamide | 16.8 | 11.5 | 10.2 | 0.31 | 10.20 | 93 |
297 | N,N'-dimethylformamide | 17.4 | 13.7 | 11.3 | 1.02 | 11.25 | 77.4 |
306 | 1,4-dioxane | 17.5 | 1.8 | 9 | 0.00 | 9.00 | 85.7 |
325 | ethyl alcohol | 15.8 | 8.8 | 19.4 | 11.76 | 15.43 | 58.6 |
328 | ethyl acetate | 15.8 | 5.3 | 7.2 | 0.00 | 7.20 | 98.6 |
333 | ethylbenzene | 17.8 | 0.6 | 1.4 | 0.00 | 1.40 | 122.8 |
366 | 1,2-dibromoethane | 19.2 | 3.5 | 6.6 | 2.83 | 5.96 | 86.6 |
385 | ethylenediamine | 16.6 | 8.8 | 17 | 0.54 | 16.99 | 67.3 |
396 | formaldehyde | 12.8 | 14.4 | 15.4 | 0.00 | 15.40 | 36.9 |
398 | formic acid | 14.6 | 10 | 22.12 | 19.86 | 9.76 | 37.9 |
404 | furfural | 18.6 | 14.9 | 7 | 0.02 | 7.00 | 83.2 |
417 | hexane | 14.9 | 0 | 0 | 0.00 | 0.00 | 131.4 |
429 | isopentyl acetate | 15.3 | 3.1 | 7 | 0.00 | 7.00 | 150.2 |
438 | isophorone | 17 | 8 | 5 | 0.00 | 5.00 | 150.3 |
456 | methyl alcohol | 14.7 | 12.3 | 22.3 | 13.97 | 17.38 | 40.6 |
464 | methyl acetate | 15.5 | 7.2 | 7.6 | 0.04 | 7.60 | 79.8 |
467 | methyl acrylate | 15.3 | 6.7 | 9.4 | 0.03 | 9.40 | 90.7 |
481 | methyl ethyl ketone | 16 | 9 | 5.1 | 0.06 | 5.10 | 90.2 |
491 | 4-methyl-2-pentanone | 15.3 | 6.1 | 4.1 | 0.04 | 4.10 | 125.8 |
531 | nitrobenzene | 20 | 10.6 | 3.1 | 0.34 | 3.08 | 102.7 |
598 | pyridine | 19 | 8.8 | 5.9 | 0.06 | 5.90 | 80.9 |
617 | tetrahydrofuran | 16.8 | 5.7 | 5.7 | 0.09 | 5.70 | 81.9 |
637 | toluene | 18 | 1.4 | 2 | 0.02 | 2.00 | 106.6 |
649 | trichloroethylene | 18 | 3.1 | 5.3 | 4.75 | 2.36 | 90.1 |
659 | triethyl phosphate | 16.7 | 11.4 | 9.2 | 0.01 | 9.20 | 170.8 |
670 | 2,2,4-trimethylpentane iso-octane | 14.1 | 0 | 0 | 0.00 | 0.00 | 165.5 |
698 | o-xylene | 17.8 | 1 | 3.1 | 0.00 | 3.10 | 121.1 |
814 | p-chlorotoluene | 19.1 | 6.2 | 2.6 | 0.03 | 2.60 | 119.1 |
997 | 2-methyltetrahydrofuran | 16.9 | 5 | 4.3 | 0.11 | 4.30 | 100.2 |
1016 | ethylacetoacetate | 16.5 | 7.3 | 8.3 | 0.00 | 8.30 | 127.3 |
1037 | methyl acetoacetate | 16.4 | 8.6 | 8.9 | 0.02 | 8.90 | 108.3 |
1043 | propionic anhydride | 15.8 | 9 | 7.7 | 0.00 | 7.70 | 129.4 |
1145 | dimethyl maleate | 16.3 | 8.3 | 9.8 | 0.20 | 9.80 | 125.5 |
SOM: Self Organization Map Neural Network
|
Study on solutions adsorption behavior of Pigments by measuring heat of wetting
This is Japanese paper written by painting company "Kansai-Paint".
They measure heat of sorption and heat of wetting for several pigments.
I showed the HSP of solvents and donor acceptor number for their study solvents.
In the original paper, they found correlation dH(hydrogen term) with heat of sorption and heat of wetting.
So, this time, I check the correlation dHdo, dHac with heat of sorption and heat of wetting.
dD | dP | dH | Vol | dHdo | dHac | |
diethyl ether | 15.49 | 2.9 | 4.6 | 104.7 | 0 | 4.6 |
cyclohexane | 16.8 | 0 | 0.2 | 108.9 | 0 | 0.2 |
xylene | 17.8 | 1 | 3.1 | 121.1 | 0 | 3.1 |
toluene | 18 | 1.4 | 2 | 106.6 | 0 | 2 |
benzene | 18.4 | 0 | 2 | 89.5 | 0.06 | 1.99 |
1,4-dioxane | 17.5 | 1.8 | 9 | 85.7 | 0.12 | 8.99 |
aniline | 20.1 | 5.8 | 11.2 | 91.6 | 5.15 | 9.95 |
butanol | 16 | 5.7 | 15.8 | 92 | 9.63 | 12.52 |
propyl alcohol | 16 | 6.8 | 17.4 | 75.1 | 10.3 | 14 |
ethyl alcohol | 15.8 | 8.8 | 19.4 | 58.6 | 11.6 | 15.5 |
methyl alcohol | 14.7 | 12.3 | 22.3 | 40.6 | 13.4 | 17.8 |
propylene glycol | 16.8 | 10.4 | 21.3 | 73.7 | 12.2 | 17.5 |
ethylene glycol | 17 | 11 | 26 | 55.9 | 16.2 | 20.3 |
Water | 15.5 | 16 | 42.3 | 18 | 38.9 | 16.6 |
heat of sorption and heat of wetting for TiO2
The author's conclusion is that TiO2 is the Basic Pigment and interact Acidic Solvents.
dH donor and heat of sorption plot is almost same above.
Quinacridone A is believed to Acidic Pigment. So dH acceptor and heat of sorption plot, we can easily understand of this phenomena.
But heat of wetting is something very difficult to understand.
Solubility parameter and oral absorption
European Journal of Pharmaceutics and Biopharmaceutics 48 (1999) 259ー263
Luigi G. Martini*, Paul Avontuur, Ashley George1, Richard J. Willson, Patrick J. Crowley
namme | % Oral absorption | dD | dP | dH | dHdo | dHac |
Metoprolol | 102 | 17.59 | 5.93 | 9.55 | 9.30 | 2.16 |
Nordiazepam | 99 | 21.33 | 11.24 | 1.06 | 1.02 | 0.26 |
Diazepam | 97 | 20.46 | 8.35 | 1.46 | 1.44 | 0.26 |
Oxprenolol | 97 | 17.44 | 6.56 | 10.86 | 10.78 | 1.30 |
Phenazone | 97 | 18.92 | 6.67 | 8.06 | 8.05 | 0.21 |
Alprenolol | 96 | 17.44 | 5.80 | 9.57 | 9.42 | 1.70 |
Practolol | 95 | 18.24 | 9.89 | 12.81 | 11.57 | 5.49 |
Pindolol | 92 | 18.82 | 7.57 | 10.73 | 9.28 | 5.40 |
Metolazone | 64 | 20.81 | 12.09 | 9.15 | 8.89 | 2.16 |
Tranexamic acid | 55 | 17.43 | 6.07 | 11.81 | 9.49 | 7.03 |
Atenolol | 54 | 18.26 | 8.59 | 12.67 | 11.43 | 5.46 |
Sulpride | 36 | 19.36 | 14.79 | 11.70 | 10.98 | 4.04 |
Mannitol | 26 | 17.29 | 17.57 | 50.02 | 40.36 | 29.56 |
Foscarnet | 17 | 20.65 | 30.71 | 47.21 | 43.49 | 18.38 |
Sulphasalazine | 12 | 19.23 | 12.96 | 12.17 | 8.59 | 8.63 |
Olsalazine | 2.3 | 17.77 | 9.52 | 17.03 | 8.18 | 14.94 |
Lactulose | 0.6 | 18.99 | 16.61 | 42.53 | 35.26 | 23.78 |
Raffinose | 0.3 | 18.66 | 16.34 | 39.34 | 32.94 | 21.50 |
In this case, Oral Absorption and dHac have very strong correlation.
Acid nature of stomach may play some role.
This study have just started.
And we ourselves did not understand completely.
So, we are not sure we add this dHdo, dHac number in ver. 3.1.X.
It will depend on user's feed back.
You can use dHdo, dHac in HSPiP V.3.1.X
HSPiP(Hansen Solubility Parameters in Practice)The first edition of HSPiP that appeared in November, 2008, greatly enhanced the usefulness of the Hansen solubility parameters (HSP). The HSP values of over 1200++ chemicals and 500 polymers are provided in convenient electronic format and have been revised and updated using the latest data sources in the second edition (March, 2009). A third edition of the HSPiP appeared in March, 2010. There are now 10,000 compounds in the HSP file which also includes data on density, melting point, boiling point, critical parameters, Antoine constants and much more. The user is able to carry out many different sorts of optimisations of solubility, evaporation, diffusion, adhesion, create their own datasets (automatically if required) and explore the huge range of applications for HSP in coatings, paints, nanoparticles, cosmetics, pharma, organic photovoltaics and much more. The 3rd Edition v3.1 was released on 12 December 2010. Current users can upgrade free (now v3.1.09) by downloading the latest .msi installer from http://hansen-solubility.com The 4th Edition v4.0.x was released on 2 Jan. 2013. The Current users can upgrade with free charge. 2013.1.28 The Visual How to manual of HSPiP. You can understand what HSPiP can do. |
From HSPiP ver. 4, you can use 4D HSP more effectively. Please try Power Tool!
Search Solvents mixture.