Dimethyl Sulfoxide (DMSO) Solubility Data
Bulletin # 102B
Introduction DMSO, one of the strongest organic solvents, has been used commercially for over forty years. It is an effective solvent for a wide array of organic materials, including many polymers. DMSO also dissolves many inorganic salts, particularly transition metals nitrates, cyanides and dichromates. DMSO is miscible with water and most organic liquids. This bulletin summarizes solubility of the following materials in DMSO: Organics (pages 2-3) Active pharmaceutical Ingredients (pages 4-6) Resins and polymers (pages 8-10) Inorganics (pages 10-11) Gases (page 12) Pharmaceutical Excipient Solubility Data (pages 16-17)
Oct 2007
Gaylord Chemical Company, L.L.C. (GCC) is the worlds leading provider of Dimethyl Sulfoxide (DMSO) solutions. Beginning in the early 1960s ,GCC has been dedicated to the development of new uses for DMSO. In order to meet customer-specific needs, GCC has pioneered the development of multiple grades of DMSO, including DMSO USP.
Gaylord Chemicals solutionsbased approach has contributed to the development and growth of New! DMSO Gel Preparation Data (pages 18-19) industries including pharmaceuticals, hydrocarbons, electronics, polymers, coatings, Data related to the solvent properties of DMSO are given in tables on the following agricultural chemicals, and pages: industrial cleaners.
Relative Hansen Solubility Parameter Data (page 12) Gaylord Chemicals headquarters Suggested DMSO Formulations for Industrial Solvent Replacement (page 14) are located in Slidell, Louisiana Hansen Solubility Parameter Data for Selected Polymers (page 14) with manufacturing, research, Solubility of Selected Polymers in DMSO / Tetralin mixtures (pages 14-15) and development facilities in Solubility of Selected Polymers in DMSO / MIBK mixtures (page 15) nearby Bogalusa, Louisiana. Appendix: Using Three Component Solubility Parameter Methodology in GCC remains the only producer Formulating Industrial Solvent Mixtures (Page 16)
of DMSO in the Western Hemisphere.
Gaylord Chemical Company, L.L.C.
Your Global Leader For DMSO Solutions!
P.O. Box 1209 Slidell, LA 70459-1209 USA 1.800.426.6620 Office 1.985.649.0068 Fax info@gaylordchemical.com
Table 1
Solubility of Organic Materials in DMSO
Solubility Grams/100 cc DMSO Solubility Grams/100 cc DMSO
Material Acetic acid Acetone Acrawax Acrawax B Aniline Anthracene Beeswax Benzene Benzidine Benzidine methane Sulfonate Bromoethane Butenes n-Butyl acetate Butly carbitol Calcium methyl sulfonate Camphor Candelilla wax Carbon Carbon disulfide Carbon tetrachloride Carbowax 600 Carbowax 6000 Carnauba wax Castor oil Ceresin wax Chloroform Chlorosulfonic acid Citric acid Coconut oil (Misc.@160C) Cresylic acid Cumene Cyclohexane Cyclohexene Cyclohexylamine Decalin n-Decane Di-n-butylamine o-Dichlorobenzene
20-30C Miscible Miscible <1 Insoluble Miscible 2 Miscible Soluble Insoluble Miscible 2.1 Miscible Miscible Soluble Soluble Insoluble 90 Miscible Miscible Insoluble Miscible
90-100C >1 4 <1 -
Material p-Dichlorobenzene S-Dichlorodiphenyltrichloroethane Dicyandiamide Dicyclohexylamine Diethanolamine Diethylamine Diethyl ether bis-(2-ethylhexyl)amine Diethyl sulfide Di-isobutyl carbinol
20-30 C Very Soluble 4 40 4.5 Miscible Miscible Miscible 0.7 Miscible Miscible 3.3 11 4.4 Miscible Miscible 33.9 Miscible Very soluble 10 >100 0.38 3.5 Soluble Soluble Soluble Insoluble Miscible Miscible Miscible Miscible Miscible Miscible Miscible Miscible 54 Miscible < 0.05 2.9 24
90-100C 100
Di-isobutylene (0.6% DMSO is soluble in di-isobutylene) Disopropyl ether Dimethyl ether Dimethyl formamide Dimethyl sulfide Dimethyl sulfone Dioxane Diphenyl Dipentene Dodecanol n-Dodecane Dodecylbenzene (Neolene 400)
Miscible
Soluble <1
8 <1 <1
Dye- Burnt Sugar Dye- FD&C Blue Dye- Pistachio Green B 1-Eicosanol Ethyl benzoate Ethyl alcohol Ethyl bromide
Miscible Reacts > 70 0.3 Miscible Miscible 4.67 Miscible Miscible 4.5 0.7 11 Miscible 1.3
Reacts
Ethyl ether Ethylene dichloride Formalin (37%) Formamide Formic acid Glucose Glycerine Glycine Hexane 4-Hydroxy benzoic Acid
0.1
Table 1, Continued
Solubility of Organic Materials in DMSO
Solubility Grams/100 cc DMSO Solubility Grams/100 cc DMSO
Material Hy-Wax 120 Imidazole Isophthalic acid Isoprene Kerosene Lanolin, hydrous Lauryl amide (Armid 12) Lorol 5 Lubricating oil Methionine Methyl borate Methyl caprate Methyl iodide Methyl isobutyl ketone Methyl laurate Methyl mercaptan N-methyl morpholine Methyl palmitate Methyl salicylate Methyl sulfonic acid Methylene chloride Microcrystalline wax Morpholine Naphthalene Neoprene Nitrobenzene Oleic acid Ouricuri wax Oxalic acid Palmitic acid Paraffin Paraformaldehyde Paradichlorobenzene Pentaerythritol n-Pentane Pentene 1 &2 Perchloric acid Petroleum ether (DMSO soluble 0.3-0.5% in petroleum ether) Phenol
20-30C 80 68 Miscible 0.5 10 Miscible 0.4 0.1 Miscible Miscible Miscible 7 40 (Reacts) Miscible Immiscible Miscible Miscible Miscible
90-100C <1 76
11 (gets cold) > 20
Material 20-30C Phosphoric acid Miscible Phosphorus trichloride Reacts vigorously Phthalic acid 90 Picric acid Soluble Pyridine Miscible Pyrogallol 50 Rosin > 100 Rosin soap (Hercules Dresinate X) Slightly soluble Sevin 50 Silicon tetrachloride Sorbitan sesquioleate Sorbitan trioleate Sorbitol Soybean oil Reacts vigorously 2.5 Miscible 60 0.6
90-100C
0.9
0.3 Miscible Reacts Miscible
> 180
Misc. 130-180C
<1 Miscible 40 Insoluble Miscible Miscible Miscible Insoluble
Succinic acid Sugar (sucrose) Sulfamic acid Sulfuric acid Tallow Tallow amide, hydrogenated (Armour Armide HT) Terephthalic acid Tetra hydrophthaIic anhydride Tetralin Tetrapropylene Thiourea Toluene Toluene di-isocyanate Tributylamine Tricresyl phosphate Triethanolamine laurylsulfate Triethanolamine Triethylamine Trinitrotoluene Turpentine Urea
30 30 40 Miscible Insoluble Insoluble 26 50 Miscible 1 40 Miscible Miscible 0.9 Miscible Soluble Miscible 10 Soluble 10 40
100
1.9 > 40 33
85
1 38 100 Insoluble Insoluble Slightly soluble 56 5-10 30 0.35 7.1 Reacts violently
110
3 >100
Xylene
Miscible
Table 2
Solubilities of Active Pharmaceutical Ingredients in DMSO
Pharmaceutical Nomenclature CAS Number Solubility g/100ml DMSO@25oC 84.3 4.9 15.4 0.6 N/A 549-18-8 1397-89-3 63-05-8 1134-47-0 1134-47-0 N/A 5593-20-4 58-85-5 51333-22-3 18010-40-7 2444-46-4 8023-77-6 298-46-4 15686-71-2 50-63-5 9007-28-7 24729-96-2 25122-46-7 20.4 25.4 0.0 5.5 0.0 38.5 0.0 89.6 23.4 49.9 11.6 19.3 25.7 6.9 0.0 0.0 0.0 22.4 40.5 5.6 23593-75-1 64-86-8 5.4 42.6 10.2 59865-13-3 154-17-6 50-02-2 46.1 19.0 60.6 Solubility g/100g DMSO@25oC 77.0 4.5 14.0 0.5 18.6 23.2 0.0 5.0 0.0 35.1 0.0 81.8 21.4 45.6 10.6 17.6 23.5 6.3 0.0 0.0 0.0 20.5 37.0 5.1 4.9 38.9 9.3 42.0 17.4 55.3 Solubility g/100ml Solution@25oC 43.5 4.3 12.3 0.5 15.7 18.8 0.0 4.8 0.0 26.0 0.0 45.0 17.6 31.3 9.6 15.0 19.0 5.9 0.0 0.0 0.0 17.0 27.0 4.8 4.7 28.0 8.5 29.6 14.8 35.6
Acetominophen Acetyl-D-Glucosamine Acyclovir USP Albuterol Sulfate Aloe Vera Powder Freeze Dried 200:1 Aamitriptyline Hydrochloride USP Amphotericin B USP (Oral Grade) Androstendione Baclofen Beclomethasone Dipropionate USP Beta Glucan (1,3) FG Betamethasone Dipropionate USP Biotin (D) USP (Vitamin H) Budesonide Bupivacaine Hydrochloride USP Capsaicin Synthetic Capsicum Oleoresin USP (Liquid) Carbamazepine USP Cephalexin USP Chloroquine Diphosphate Chondroitin Sulfate Clindamycin phosphate Clobetasol Propionate USP Clonidine Hydrochloride USP Clotrimazole USP Colchicine USP Cyclobenzaprine USP Cyclosporin (A) USP Deoxy-D-Glucose (2) Dexamethasone USP
103-90-2 10036-64-3 59277-89-3
Table 2, Continued
Solubilities of Active Pharmaceutical Ingredients in DMSO
Pharmaceutical Nomenclature Dextromethorphin Dichlofenac Sodium Dihydroepiandrosterone Diiodohydroxyquin (Iodoquinol) USP Dimercatopropanesulfonic Acid Na Salt (2,3) Dimercaptosuccinic Acid Edetate Disodium USP Ergoloid Mesylate USP Erythromycin USP Estradiol USP (E2) Estradiol Cypionate USP Estradiol Valerate USP Estriol USP (E3) Estrone USP (E1) Fluorouracil-(5 FU) USP Glucosamine Hydrochloride (D) Guaifenesin USP Haloperidol USP Hydrocortisone Acetate USP Ketamine Hydrocortisone USP Hydroxyprogesterone Caproate USP Ibuprofen USP Indomethacin USP Itraconazole HCl USP CIII Ketoconazole USP Ketoprofen Levamisole HCl USP (Vet Use) 53-43-0 83-73-8 4076-02-2 N/A 6381-92-6 8067-24-1 114-07-8 50-28-2 313-06-4 979-32-8 50-27-1 53-16-7 51-21-8 66-84-2 93-14-1 52-86-8 50-03-3 50-23-7 630-56-8 15687-27-1 53-86-1 84625-61-6 1867-66-9 65277-42-1 22071-15-4 16595-80-5 CAS Number Solubility g/100ml DMSO@25oC 70.9 54.7 61.2 9.9 92.6 91.8 9.3 0.0 21.6 100.3 90.7 97.1 0.0 7.9 17.3 9.5 131.2 0.0 24.5 39.3 11.6 412.1 119.2 0.0 4.0 3.4 54.2 5.2 Solubility g/100g DMSO@25oC 64.7 49.9 55.8 9.0 84.5 83.8 8.5 0.0 19.7 91.6 82.8 88.7 0.0 7.2 15.8 8.7 119.8 0.0 22.4 35.9 10.6 376.2 108.8 0.0 3.6 3.1 49.5 4.7 Solubility g/100ml Solution@25oC 39.3 33.3 35.8 8.3 45.8 45.6 7.8 0.0 16.5 47.8 45.3 47.0 0.0 6.7 13.7 8.0 54.5 0.0 18.3 26.4 9.6 79.0 52.1 0.0 3.5 3.1 33.1 4.5
Table 2, Continued
Solubilities of Active Pharmaceutical Ingredients in DMSO
Pharmaceutical Nomenclature CAS Number Solubility g/100ml DMSO@25oC 163.0 311.8 7.2 10.8 0.0 6.3 2.2 4.3 93.7 20.2 8.6 22916-47-8 22204-53-1 98-92-0 21829-25-4 1400-61-9 37.5 37.7 7.9 47.8 7.6 15.2 6493-05-6* 36.1 94.8 36322-90-4 50-24-8 53-03-2 145-13-1 5.8 23.2 42.8 2.4 7.6 57-83-0 4.4 Solubility g/100g DMSO@25oC 148.8 284.6 6.5 9.9 0.0 5.7 2.0 4.0 85.5 18.5 7.9 34.2 34.4 7.2 43.7 6.9 13.9 32.9 86.6 5.3 21.2 39.1 2.2 7.0 4.1 Solubility g/100ml Solution@25oC 59.8 74.0 6.1 9.0 0.0 5.4 2.0 3.8 46.1 15.6 7.3 25.5 25.6 6.7 30.4 6.5 12.2 24.8 46.4 5.0 17.5 28.1 2.2 6.5 3.9
Lidocaine USP Lipoic Acid, DL-alpha (DL-Thiotic Acid) Loperamide Hydrochloride USP Lorazepam USP Civ NDC: 51927000502 Manganese Chloride Tetrahydrate USP Mebendazole USP Medroxypregesterone Acetate Megestrol Acetate USP Methimazole USP Methotrexate USP Metronidizole Miconazole Base USP Naproxen USP Niacinamide USP Nifedipine USP Nystatin USP Panthenol Pentoxifylline Phenytoin USP (Diphenyl Hydantoin) Piroxicam USP Prednisolone Prednisolone USP Pregnenolone Prochlorperazine dimaleate Progesterone USP
137-58-6 1077-28-7 34552-83-5 846-49-1 13446-34-9 31431-39-7 71-58-9 595-33-5 60-56-0 59-05-2
Table 2, Continued
Solubilities of Active Pharmaceutical Ingredients in DMSO
Pharmaceutical Nomenclature CAS Number Solubility g/100ml DMSO@25oC 24.9 53.5 22.1 0.0 130-40-5 13292-46-1 22199-08-2 54965-24-1 70024-40-7 0.0 20.6 0.0 10.8 10.6 30.2 94-24-6 60-54-8 148-79-8 552-22-7 53902-12-8 369.9 19.0 10.8 3.0 41.1 17.2 57-13-6 N/A 152-11-4 79-81-2 68-19-9 67-97-0 10191-41-0 65-19-0 13463-41-7 45.2 11.5 19.5 11.9 0.0 0.0 0.0 0.0 0.0 Solubility g/100g DMSO@25oC 22.7 48.8 20.2 0.0 0.0 18.8 0.0 9.9 9.6 27.6 337.6 17.4 9.9 2.8 37.6 15.7 41.2 10.5 17.8 10.9 0.0 0.0 0.0 0.0 0.0 Solubility g/100ml Solution@25oC 18.5 32.8 16.8 0.0 0.0 15.8 0.0 9.0 8.8 21.6 77.2 14.8 9.0 2.7 27.3 13.6 29.2 9.5 15.1 9.8 0.0 0.0 0.0 0.0 0.0
Promethazine Hydrochloride USP Propanolol Hydrochloride Pyracetam Riboflavin-5-Phosphate Sodium USP Riboflavin-5-Phosphate Sodium USP Rifampin USP Silver Sulfadiazine USP Tamoxifen Citrate USP Terazosin Hydrochloride Dihydrate Testosterone Tetracaine USP Tetracycline USP Thiabendazole USP Thymol Iodide Purified Tranilast Triamycynilone Urea USP Vancomycin Hydrochloride Verapamil Hydrochloride USP Vitamin A Palmitate (18,000 U/mL) Vitamin B12 USP (Cyanocobalamin) Vitamin D3 (2400 U/mL) Vitamin E Yohimbine Hydrochloride Zinc Pyrithione (48% Min. Aq. Dis.)
58-33-3 318-98-9 7491-74-9
Table 3
Solubility of Resins and Polymers in DMSO
Material Aminoplasts Melamine Formol Urea formol Polyacrylics Orlon (DuPont) Acrilan (Monsanto) Verel (Eastman) Creslan (Am. Cyanamid) Polyamides Nylon 6 Nylon 6/6 Nylon 6/10 Nylon 11 Rilsan (Elf Ato) Nylon 12 Oryasol (Elf Ato) Polyimides Bismaleimide copolymers Kermid 353 (Rhone-Poulenc) Kermid 711 (Rhone-Poulenc) Polyamino bis maleimide Kermid 601(Rhone poulenc) I Polyamideimide Torlon 4203L (Amoco) Polyetherimide Ultem 100 (G.E.) Cellulose Cellulose triacetate Viscose rayon Cellophane Carboxymethyl cellulose Nitrocellulose Chlorinated Resins Butaclor MC30 (Distugil) CM3630 (Bayer) Hypalon DH70 (DuPont) Epoxies Epikote 1004 (Shell) Epon 1001 (Shell) Epon 1004 (Shell) Epon 1007 (Shell) Swells Soluble 50 50 50 20-30C Soluble Soluble >25 >5 5 Insoluble Insoluble Insoluble Insoluble Insoluble Insoluble Swells Soluble Insoluble Swells 10 Swells 20 <1 Insoluble Insoluble 10 25 at 130C with some decomposition 25 at 130C 40 at 130C 25 at 150C 40 at 150C Soluble @ 140C 20 Viscous soln. Solubility, Grams/100cc DMSO 90-100C Comments
Table 3, Continued
Solubility of Resins and Polymers in DMSO
Material Fluorinated Resins Polyvinylidene floride Foraflon (Atochem) Elastomers Viton DF801 (DuPont) Viton DF809 (DuPont) Kalrez 4079 (DuPont) Teflon (DuPont) Methacrylates Lucite 41, 45 (DuPont) Plexiglas (Rohm & Haas) Phenoplasts Modified Novalac R7522 (Ceca) R7550 (Ceca) Norsophen Resin PH 13 (CDF Chime) Polycarbonates Lexan (General Electric) Polyesters Dacron (DuPont) CX 1037 (Goodyear) Atlac (ICI-America) Poly(ethylene terephthalate) Poly(butylene terephthalate) Hytrel (DuPont) Silicones Dow Corning 803 soln. Dow Corning 805 soln. Dow Corning "Sylkyd 50" Dow Corning Z6018 (flake) Sulfur Resins Polyphenylene sulfide Ryton V107 (Philips) Polyethersulfone Victrex 660P (ICI) Ultrason E3000 (BASF) Udel (Amoco) Urethanes Vithane (Goodyear) 20-30C Solubility, Grams/100cc DMSO 90-100C Comments
Swells Swells Swells Insoluble Insoluble Insoluble <1 <1
Soluble Soluble Soluble Miscible Miscible Miscible 70 >5 >1 7 50 Dissolves at 160C; ppts at 130C
Swells Soluble Soluble Soluble 100
Table 3, Continued
Solubility of Resins and Polymers in DMSO
Solubility, Grams/100cc DMSO Material Vinyle-Polymers & Co-polymers Butvar B-76 (Monsanto) Formvar 7/70 E Monsanto) Elvanol 51-05 (DuPont) Elvanol 52-22 (DuPont) Elvanol 71-24 (DuPont) Polyvinyl pyrrolidone (GAF) Geon 101 (PVC Goodrich) Vinylite WHH (Union Carbide) Teslar (DuPont) Vinylidenes Darvan (Goodrich) Saran film (Dow) Geon 200 x 20 (Goodrich) DNA (Goodrich) Other Resinous Materials Melmac 405 (Am. Cyanamid) Neoprene Polyetherether ketone (PEEK) Polyethylene Polypropylene Polystyrene Rosin (Hercules) Penton chlorinated polyether (Hercules) Vinsol (Hercules) 20-30C 30 2 5 >5 70 Insoluble Insoluble Insoluble Insoluble >100 50
Table 4
90-100C 20 42 90 15 30 >100 10 30 30 20 Insoluble Insoluble Insoluble 5 >100 25 at 130C Very viscous Very viscous Viscous Viscous Viscous
Comments
Partially sol. at 160-170C Soln. cloudy and viscous
Sol. at 150C; ppts at 130C
SOLUBILITY OF INORGANIC MATERIALS IN DMSO Material Aluminum sulfate (18H20) Aluminum chloride Ammonium borate (3H20) Ammonium carbonate(H20) Ammonium chloride Ammonium chromate Ammonium dichromatec Solubility, Grams/100cc DMSO 25C 90-100C Material Insoluble Reacts 10 1 Insoluble 1 50 10 5 Ammonium nitrate Ammonium thiocyanate Barium nitrate Beryllium nitrate(4H2O) Bismuth trichloride Boric acida Bromine Solubility, Grams/100cc DMSO 90-100C 25C 80 30 1 10 1 45 Reacts
10
Table 4, Continued
SOLUBILITY OF INORGANIC MATERIALS IN DMSO
Cadmium chlorideb Cadmium iodide Calcium chloride Calcium dichromate(3H2O)c Calcium nitrate(4H2O) Ceric ammonium nitrate Cobaltous chloride (6H2O) Cupric acetate(H2O) Cupric bromideb Cupric chloride(2H2O) Cupric sulfate(5H2) Cuprous iodide Ferric ammonium sulfate Ferric chloride(6H2O) Ferrous chloride(4H2) Gold chloride Iodine Lead chlorideb Lead nitrate Lithium bromide Lithium chloride Lithium dichromate(2H2O)c Lithium iodide Lithium nitrate Lithium perchloratec Magnesium chloride(6H2O) Magnesium nitrate (6H20) Manganous chloride (4H20) Mercuric acetate Mercuric bromide Mercuric iodide Mercuric sulfate Molybdenum bromide Nickel chloride(6H20) Nickel nitrate (6H20) Potassium bromide
20 30 Insoluble 50 30 1 30 Insoluble 1 Insoluble <0.01 1 at 30C Insoluble 30 30 5 >100 10 20 31.4 10.2 10 41.1 10 31.5 1.0 40 20 100 90 100 <0.01 1 60 60 6.5 90 90
Potassium chloride Potassium cyanide Potassium hydroxide Potassium iodide Potassium nitrate Potassium nitrite Misc. m.p. Potassium perchloratec 6 27 Potassium thiocyanate Silver iodide Silver nitrate Sodium sulfate Misc. m.p. Sodium azide Sodium chloride Sodium cyanide Sodium dichromate(2H2O)c Sodium hydroxide Sodium iodide Sodium nitrate Sodium nitrite Sodium perchloratec Sodium thiocyanate Stannic chloride Stannous chloride(2H2O) Strontium bromide(6H2O) Strontium chloride(2H2O) Sulfur dichloride Sulfur monochloride Tungsten hexachloride Uranyl nitrate (6H2O) Vanadium chloride Zinc acetate Zinc chlorideb Zinc nitrate(6H2O) Zinc sulfate 20 @150C Silver chloride
0.2 1 0.013 20 12 2 38 20 <0.01 <0.01 130 <0.01 <1.0 0.4 1 12 0.035 30 20 20 24.2 1 25 40 5 10 Reacts violently Reacts violently 5 30 1 >100 30 55 <0.01 10 1.6 180 50 20 2
60
a) @20.3 b) possible reaction c) not recommended due to safety considerations
11
Solubility of Gases in DMSO (At Atmospheric Pressure, 20 oC)
Grams Gas/ 100 Grams Solution Acetylene Ammonia Butadiene Butane Butylenes (mixed) Carbon dioxide Carbon monoxide Ethane Ethylene Ethylene oxide Freon 12 Helium Hydrogen Hydrogen sulfide Isobutylene Methane Nitric oxide (NO) Nitrogen Nitrogen dioxide(NO2,N2O4) Oxygen Ozone Propane Propyne Sulfur dioxide 57.4 (reacts) 2.99 2.6 4.35 2.05 .05 <0.01 6.85 x 10-2 .32 60.0 1.8 1.46 x 10-4 1.95 x 104 0.5 (reacts) 2.5-3.0 7.92 x 10-3 0.00 2.99 x 10-3 Miscible (possible reaction) 6.44 x 10-3 Reacts 1.8 58.2 0.049 Gas Volume/ Volume of DMSO 28.1 40.0 31.0 4.8 2.86 0.56 2.8 306.0 3.7 0.89 x 10-2 2.39 x 10-2
Table 5
0.6
Table 6
Relative Hansen Solubility Parameter Data
Solvent DIMETHYL SULFOXIDE (DMSO) Butyrolactone Dimethylacetamide (DMAC) Dimethylformamide (DMF) N-Methyl-2-pyrrolidone (NMP) Propylene Carbonate Sulfolane d 9.0 9.3 8.2 8.5 8.8 9.8 9.0 P 8.0 8.1 5.6 6.7 6.0 8.8 7.4 h 5.0 3.6 5.0 5.5 3.5 2.0 5.3 t 13.0 12.8 11.1 12.1 11.2 13.3 12.8
The units for solubility parameters in this table are (cal /cm 3),1/2. SI units (J/ cm3)1/2 can be obtained by multiplying by 2.0455.
12
Table 7
Suggested DMSO Formulations for Industrial Solvent Replacement
Solvents to Be Replaced d Acetone Butyl cellosolve 7.6 7.8 p 5.1 2.5 h 3.4 6.0 Theoretical Replacement Mixture Weight % 65% DMSO 35% Aromatic 150 10% DMSO 30% Aromatic 150 60% Isopropyl alcohol 100% DMSO 33% DMSO 67% Butyl alcohol 40% DMSO 60% Aromatic 100 67% DMSO 33% Amyl acetate 80% DMSO 20% 2-methyl butanol 30% DMSO 70% Aromatic 100 20% DMSO 60% Butyl alcohol 20% Amyl acetate 50% DMSO 40% Aromatic 100 10% n-Butanol 20% DMSO 80% MIBK 67% DMSO 33% Amyl acetate 80% DMSO 20% 2-methyl butanol 30% DMSO 70% Aromatic 100 20% DMSO 60% Butyl alcohol 20% Amyl acetate 50% DMSO 40% Aromatic 100 10% n-Butanol 20% DMSO 80% MIBK 40% DMSO 60% Aromatic 150 45% DMSO 55% Toluene d 8.8 p 5.0 h 3.6
8.0 9.0 8.1 8.9 8.6 8.6 8.9
2.7 8.0 4.2 3.2 5.3 6.6 2.5
5.9 5.0 7.0 2.4 5.0 5.4 2.0
Butyrolactone Cellosolve Cyclohexanone Dimethyl acetamide Dimethyl formamide Ethyl amyl ketone Ethylene glycol butyl ether acetate Isophorone
9.3 7.9 8.7 8.2 8.5 8.0 8.1
8.1 4.5 3.1 5.6 6.7 2.5 2.8
3.6 7.0 2.5 5.0 5.5 2.1 6.7
8.0
3.3
6.6
8.1
4.0
3.6
8.9 7.8 8.6 8.6 8.9
4.1 3.8 5.3 6.6 2.5
3.5 2.5 5.0 5.4 2.0
Methyl ethyl ketone Dimethyl acetamide Dimethyl formamide Ethyl amyl ketone Ethylene glycol butyl ether acetate Isophorone
7.8 8.2 8.5 8.0 8.1
4.4 5.6 6.7 2.5 2.8
2.5 5.0 5.5 2.1 6.7
8.0
3.3
6.6
8.1
4.0
3.6
8.9 7.8 8.7 8.9
4.1 3.8 3.1 3.6
3.5 2.5 2.7 2.6
Methyl ethyl Ketone Methylene chloride Nitrobenzene
7.8 8.9 9.8
4.4 3.1 4.2
2.5 3.0 2.0
13
Table 7, Continued
Suggested DMSO Formulations for Industrial Solvent Replacement
Solvents to be Replaced NMP Pentoxone (discontinued) Propylene carbonate Sulfolane 8.8 7.3 9.8 9.0 6.0 4.2 8.8 8.1 3.5 2.8 2.0 3.6 Theoretical Replacement Mixture 70% DMSO 30% Aromatic 100 50% DMSO 50% Aromatic 100 100% DMSO 100% DMSO
Table 8
8.9 8.9 9.0 9.0
5.4 3.9 8.0 8.0
3.6 2.8 5.0 5.0
Hansen Solubility Parameter data for Selected Polymers
Polymer dd dP dh Radius
Polymethylmethacrylate Rohm & Haas Epoxy - "Epicote" 1001 Shell Chemical Polystyrene BASF Polyvinyl acetate "Mowilith" 50 Farbwerke Hoechst Nitrocellulose 1/2 sec. H 23 A. Hagedorn Cellulose acetate "Cellidora" A. Bayer A.G. Polyester "Desmophen" 850 A. Bayer A.G. Polyvinyl chloride "Vipla"KR Montecatini
9.1 10.0 10.4 10.2 7.5 9.1 10.5 8.9
5.1 5.9 2.8 5.5 7.2 6.2 7.3 3.7
3.7 5.6 2.1 4.7 4.3 5.4 6.0 4.1
4.2 6.2 6.2 6.7 5.6 3.7 8.2 1.7
Tables 9 and 10 illustrate how the solvency of a mixture for selected polymers can be related to the composition of the mixture. Predicted solvencies of mixtures of DMSO and tetralin or DMSO and methyl isobutyl ketone for these eight polymers are tabulated. A solvency value of 100 was assigned to mixtures at the center of the HSP envelope and a value of 0 to mixtures at the envelope boundary. These tables also show how solvency changes with the composition of the mixture, with ratio of the solvents selected, and show the composition of maximum solvency for each polymer and solvent pair.
Table 9
Solubility of Selected Polymers in DMSO/Tetralin Mixtures
Polymer DMSO % Tetralin%
Polymethylmethacrylate Rohm & Haas Epoxy - "Epicote" 1001 Shell Chemical Polystyrene BASF
Solvency(1) Versus Mixture Composition 100 0 42 77 ns 80 20 87 85 35 60 40 99 81 70 50 50 93 40 60 80 60 87 20 80 38 32 91 0 100 ns ns 84
14
Table 9, Continued
Solubility of Selected Polymers in DMSO/Tetralin Mixtures
Polymer DMSO % Tetralin%
Polyvinyl acetate "Mowilith" 50 Farbwerke Hoechst Nitrocellulose 1/2 sec. H 23 A. Hagedorn Cellulose acetate "Cellidora A. Bayer A.G. Polyester "Desmophen" 850 A. Bayer A.G. Polyvinyl chloride "Vipla" KR Montecatini
If Solvency <0, rating is ns indicating not soluble.
Solvency(1) Versus Mixture Composition 100 0 73 67 74 85 ns 80 20 86 65 89 83 ns 60 40 89 65 61 74 ns 68 50 50 84 40 60 77 4 0 57 ns 20 80 57 ns ns 35 ns 0 100 28 ns ns 5 ns
Table 10
Solubility of Selected Polymers in DMSO/MIBK Mixtures
Polymer DMSO, % MIBK, % Polymethylmethacrylate Epoxy - Epicote 1001, Shell Chemical Polystyrene Polyvinyl acetate Mowilith 50, Farbwerke Hoechst Nitrocellulose 1/2 sec. H 23 Cellulose acetate Polyester- Desmophen 850, Bayer MaterialScience Polyvinyl chloride
MIBK-methyl isobutyl ketone If Solvency <0, rating is ns indicating not soluble.
Solvency(2) Versus Mixture Composition 100 80 60 40 20 0 20 40 60 80 42 77 ns 73 67 74 85 ns 77 73 15 72 83 81 74 ns 84 58 27 64 82 54 58 ns 67 38 30 43 69 0 39 ns 38 9 21 28 51 ns 16 ns
0 100 0 ns 12 6 27 ns ns ns
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Table 11
Pharmaceutical Excipient Solubility Data Excipient Brand Name (Supplier) Solubility Description practically insoluble/insoluble practically insoluble/insoluble practically insoluble/insoluble practically insoluble/insoluble very soluble sparingly soluble sparingly soluble sparingly soluble freely soluble slightly soluble practically insoluble/insoluble practically insoluble/insoluble practically insoluble/insoluble practically insoluble/insoluble very soluble very soluble very slightly soluble practically insoluble/insoluble practically insoluble/insoluble practically insoluble/insoluble freely soluble practically insoluble/insoluble
Butyl and other patch adhesives Duro-TAK (National Starch) Carnauba Wax Carrageenan NF Cetyl Alcohol NF Ethanol (absolute) Ethylcellulose NF Hydroxypropyl cellulose Hypromellose USP Lactose Lanolin Lecithin Light Mineral Oil NF MgStearate NF Mineral Oil USP Oleic Acid PEG 300 NF PEG 50 Stearate PEG 8000 NF Poloxamer NF Poly (L-lactide) Poly (DL-lactide-co-glycolide) Polymethacrylates Carnauba wax, No. 1 (Aldrich) Gelcarin GP 911NF (FMC) Crodacol C-95 NF (Croda) Ethanol (Aldrich) Ethocel Standard 4 (Dow) Klucel LF (Aqualon) Methocel E3 Premium LV (Dow) - & D- Lactose Medilan Ultra (Croda) Lecithin, refined (Alfa Aesar) Drakeol 5 (Penreco) Mg Stearate (Ferro) Drakeol19 (Penreco) Oleic acid (Aldrich) Carbowax Sentry 300 (Dow) Ritox 53 (Rita) Carbowax Sentry 8000 (Dow) Lutrol F127 NF (BASF) Resomer L210 S (Boehringer Ingelheim) Resomer RG502 H (Boehringer Ingelheim) Eudragit E 100 (Rohm Pharma)
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Table 11 (continued)
Pharmaceutical Excipient Solubility Data
Excipient Polyoxyl 35 Castor Oil NF Polysorbate 80 NF Polyvinyl Alcohol Povidone USP Propylene Glycol (USP) Sorbitan Monopalmitate Soybean Oil NF Starch Pregelatinized NF Stearic Acid Sucrose Water White Petrolatum USP
Brand Name (Supplier) Cremophor EL (BASF) Tween 80 (Uniqema) PVA, fully hydrolyzed (JT Baker) Kollidon 90 F and 17 PF (BASF) Propylene Glycol (Dow) Span 40 (Uniqema) Super Refined Soybean Oil NF (Croda) Starch 1500 (Colorcon) Stearic acid, Grade I (Aldrich) Sucrose (Domino) Water Super White PET USP (Penreco)
Parts of Solvent Required for 1 Part of Solute Less than 1 From 1 to 10 From 10 to 30 From 30 to 100 From 100 to 1000 From 1000 to 10000 10,000 or over
Solubility Description very soluble very soluble practically insoluble/insoluble freely soluble very soluble insoluble practically insoluble/insoluble practically insoluble/insoluble sparingly soluble freely soluble very soluble practically insoluble/insoluble
Descriptive Term Very Soluble Freely Soluble Soluble Sparingly Soluble Slightly Soluble Very Slightly Soluble Practically Insoluble Or Insoluble
Adapted from USP 28 / NF 23 (2005) p. 9. All measurements were performed at room temperature (ca. 21oC)
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Table 12
DMSO Gel Preparation Data
Pharmaceutically acceptable gelling agents suitable for the formulation of topical / transdermal DMSO products were evaluated to understand the effect of polymer loading on formulation viscosity. Methocel is a trademark of the Dow Chemical Company.
All viscosity measurements were recorded using a Brookfield Model DV-E Digital Viscometer. using spindle 61 at 100 rpm. Gels were measured at 73F (23C). The diameter of the measurement vessel was 8 cm.
Methocel A4M: All viscosity measurements were recorded using a Brookfield Model DV-E Digital Viscometer. using spindle 61 for measurements at 0.5, 1.0 and 1.5 % polymer. Spindle 63 was used for the 2.0 % sample. Instrument settings of 100, 30, 6 and 100 RPM were used for samples containing 0.5, 1.0, 1.5, and 2.0 wt% polymer, respectively. Gels were measured at 73F (23C). The diameter of the measurement vessel was 8 cm.
Methocel E4M: All viscosity measurements were recorded using a Brookfield Model DV-E Digital Viscometer, using spindle 61. Instrument settings of 100, 30, 12 and 5 RPM were used for samples containing 0.5, 1.0, 1.5, and 2.0 wt% polymer, respectively. Gels were measured at 73F (23C). The diameter of the measurement vessel was 8 cm. Formulation included 1.0 wt% triethanolamine. Other Dow rheology modifiers currently under evaluation include: Polyox WSR N10 NF, Methocel E5 LV, Ethocel Standard 4 NF and Ethocel Standard 10
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Table 12 (continued)
DMSO Gel Preparation Data
Pharmaceutically acceptable gelling agents suitable for the formulation of topical / transdermal DMSO products were evaluated to understand the effect of polymer loading on formulation viscosity. Klucel is a trademark of Hercules Aqualon. Carbopol is a treademark of Noveon Corporation.
Klucel HF: All viscosity measurements were recorded using a Brookfield Model DV-E Digital Viscometer. using spindle 61 for measurements at 0.5, 1.0 and 1.5 % polymer. Spindle 64 was used for the 2.0 % sample. Instrument settings of 60, 2.5, 0.6 and 20 RPM were used for samples containing 0.5, 1.0, 1.5, and 2.0 wt% polymer, respectively. Gels were measured at 73F (23C). The diameter of the measurement vessel was 8 cm. Other Hercules Aqualon rheology modifiers currently under evaluation include: Klucel GF, HFX, LF, MF, EF, JF. Carbopol 941 NF : All viscosity measurements were recorded using a Brookfield Model DV-E Digital Viscometer. using spindle 64 for measurements at 1.5 % and 2.0% polymer. Spindle 61 was used for the 0.5 % sample and spindle 62 for the 1.0% sample. Instrument settings of 30, 1.0, 100 and 0.3 RPM were used for samples containing 0.5, 1.0, 1.5, and 2.0 wt% polymer, respectively. Gels were measured at 73F (23C). The diameter of the measurement vessel was 8 cm. General procedure for preparing DMSO-based gel products. DMSO-based gels are prepared using methods similar to those described by manufacturers for water-based media. The additive is sifted with stirring into DMSO and allowed to disperse over 30-60 minutes. Warming the mixture at 50C is helpful in dispersing the additive, and pH adjustment using suitable bases is often useful. In the case that less polar cosolvents are included, it may be best to form a pregel in DMSO, followed by slow addition of the less polar cosolvent. Recommended packaging materials for storage include HDPE, HDPP, or Teflon PTFE. Other Noveon rheology modifiers currently under evaluation include: Carbopol 940 NF, 934 NF, 980 NF, 934 NF, 981 NF, 1342 NF, 71G NF, 974 NF, Ultrez 10 NF, 971P NF
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The information in this booklet is based on information available to us and on our observations and experiences. However, no warranty is expressed or implied regarding the accuracy of this data, the results to be obtained from the use thereof, or that any use will not infringe any patent. Each user must establish appropriate procedures for off-loading, handling, and use of the product(s). Since conditions for use are beyond our control, we will make no guarantee of results, and assume no liability for damages incurred by off-loading, handling, or use of the product(s). Nothing herein constitutes permission, or recommendation to practice any invention covered by any patent without license from the owner of the patent.
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