Table 2.
Conditions of preparation of co-crystals by grinding method.
| # | Sample | Molar Ratio | Method of Preparation | Milling Type | Instrument Brand | Milling Jar | Balls (# and Material) | Milling Frequency | Milling Temp | Milling Time | Ref. |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1C | Nicotinamide: L-(+)-Ascorbic acid |
1:1 | Assisted by solvent | Vibrational | Mixer Mill (IST 500) InSolido Technologies | Polymethylmetacrylate | Two stainless steel balls | 30 Hz | NR | 60 min | [66] |
| 2C | Salicylic acid:2-pyridone Salicylic acid: 4-Pyridone |
1:1 | NR | Vibrational | Mixer Mill (IST 500) InSolido Technologies | Polymethylmetacrylate | Two stainless steel balls | 30 Hz | NR | 50 min | [117] |
| 3C | Ciprofloxacin- thymol |
1:2 | Assisted by solvent (EtOH) | NR | Retsch MM200 ball miller, | NR | NR | 20 Hz | NR | 30 min | [118] |
| 4C | Urea- caffeine |
1:1 | NR | Oscillatory ball | Mixer Mill MM400-Retsch GmbH, Haan | Stainless steel jar | One 15 mm stainless steel ball | 25 Hz | Room temperature | 60 min | [119] |
| 5C | Brexpiprazol-Catechol Brexpiprazol-Succinic acid |
1:1 | NR | NR | Nano Ball Mill (Fritsch Premium Line, FRITSCH GmbH, Idar-Oberstein, Germany) using | NR | Stainless steel balls | 8.3 Hz | NR | 120 min | [120] |
| 6C | Quercetin- malonic acid |
1:1 and 1:2 | Solvent drop grinding | NR | NR | NR | NR | NR | NR | 30 min | [121] |
| 7C | Paracetamol-trimethylglycine | 1:1 | NA | Planetary ball | QM-3SP2, Nanjing NTU Instrument Co. | NR | NR | 6.6 Hz | NR | 5 h | [44] |
| 8C | Meloxicam- benzoic acid |
1:1 | LAG | NR | Retsch CryoMill | NR | NR | 25 Hz | Room temperature | 30 min | [122] |
| 9C | Acetazolamide and 4-hydroxybenzoic acid |
1:1 | LAG | Planetary ball | QM-3SP04, gear type | 25 mL stainless steel milling jars | NR | 25 Hz | NR | 30 min | [123] |
| 10C | Furosemide-urea and carbamazepine-indomethacin |
1:1 | LAG | NR | Retsch MM400 ball mill | 50 mL jar, with two 5 mm stainless steel balls and drops of acetone. | NR | NR | NR | 60 min | [51] |
| 11C | Ciprofloxacin-nicotinic and isonicotinic acids |
1:1 | Assisted or not by solvent (EtOH) | NR | Retsch MM 400 mixer mill | 10 mL stainless-steel jars | 1 stainless steel ball of 7 mm diameter, 100, 500 mg sample | 30 and 15 Hz | NR | 30 min | [124] |
| 12C | Pyrazinamide-diflunisal | 1:1 | LAG | Oscillatory ball mill | Mixer Mill MM400 | 25 mL stainless steel milling jars | NR | 15 Hz | Room temperature | 60 min | [125] |
| 13C | Acetazolamide–4-aminobenzoic acid | 1:1 | With solvent | Planetary ball | Fritsch micro mill model Pulverisette 7 | 12 mL agate grinding jars | Ten 5 mm agate balls | 8.3 Hz | NR | 30 min | [67] |
| 14C | Acetazolamide-nicotinamide-2-pyridone | 1:1:1 | LAG with ethyl acetate and tetrahydrofuran solvents | Planetary ball | QM-3SP04, gear type | 25 mL stainless steel milling jars | NR | 15 Hz | NR | 60 min | [126] |
| 15C | β-Lapachone-resorcinol | 1:1 | LAG | NR | Retsh Mixer Mill (Model MW 200) | Stainless steel jar together | A stainless steel ball | 20 Hz | NR | 20 min | [127] |
| 16C | Norfloxacin-nicotinic acid | NR | NT and LAG | Ocillatory ball system | Mixer Mill MM 400, Retsch GmbH and Co | Stainless steel jars | 7 mm diameter stainless steel ball | 15 Hz | NR | 30 min | [128] |
| 17C | Chlorothiazide, D-proline, L-proline | 1:1 | NT and LAG | Oscillatory ball | Retsch (MM400, Retsch) | NR | NR | 30 Hz | NR | 30 min | [129] |
| 18C | Praziquantel, poloxamer F-127, and sucrose stearate | 20:1, 10:1, 10:2, and 10:3 | NT | High-energy vibrational ball | Mixer Mill MM 200, Retch, GmbH | 10 mL volume stainless steel grinding jars | Two 7 mm stainless steel grinding balls | 25 Hz | 28.10–30.34 °C | 30 or 90 min | [130] |
| 19C | Ferulic acid, urea, nicotinamide, and isonicotinamide (INA) | 1:1 and 1:2 | LAG | NR | Retsch Mixer Mill (model MM301) | Stainless steel grinding jar | One 7 mm stainless steel ball | 20 Hz | NR | 20 min | [131] |
| 20C | Ketoconazole, fumaric acid, and succinic acid |
1:1.1 and 1:1 | NT and LAG | Oscillatory ball | Retsch MM 400 | 25 mL stainless steel jars | One stainless steel ball | 19 Hz | NR | 60 min | [132] |
| 21C | Itraconazole: 4-aminobenzoic acid Itraconazole: 4-hydroxybenzamide |
1:1 2:1 1:2 |
LAG | Planetary micro | Fritsch planetary micro mill, Pulverisette 7 | 12 mL agate grinding jars | Ten 5 mm agate balls | 8.3 Hz | NR | 40 min | [133] |
| 22C | S-ibuprofen: nicotinamide | 1:1 | N.R | Oscillatory ball | MM400—Retsch | 10 mL ZrO2 milling jars | One ball, 10 mm | 30 Hz | NR | 60 and 10 min and 5 min pauses | [134] |
| 23C | Pyrazinamide: 4-aminosalicylic acid | 1:1 | LAG | Planetary ball | QM3SP04, gear type, Nanjing University Instrument Factory | 20 mL stainless steel grinding tank | N.R | 20 Hz | Room temperature | 40 min | [135] |
| 24C | Theophylline: 4-aminobenzoic acid | 1:1 | N.R | N.R | MM 400, Retsch, Germany | 10 mL jar 25 mL jar |
One ball, 8.74 mm, One ball, 13.72 mm |
30 Hz | N.R | Period times: 2,5,10, 15, 20, and 25 min | [136] |
| 25C | Betulin-terephthalic acid | 1:1 2:1 |
Assisted by solvent | NR | SPEX 8000 mixer mill (CertiPrep Inc., Metuchen, NJ, USA) | 60 mL steel jar | Steel balls 6 mm | NR | NR | Pre-milled: 5 min After solvent: 10 min |
[137] |
| 26C | 5-Fluorocytosine:5-fluorouracil | 1:1 | NT SDG |
Oscillatory | Mixer Mill MM400 RETSCH | 25-mL stainless steel milling jar | Two 7 mm stainless steel balls | 25 Hz | Room temperature | 90 min SDG: 60 min |
[138] |
| 27C | Nicotinamide:adipic acid (polymorph, form 2) | 1:1 | Assisted by solvent (acetonitrile) | NR | Retsch MM400 mill (in-house modified) | Stainless steel milling jar | Two 7 mm stainless steel balls | 30 Hz | NR | 60–90 min | [139] |
LAG: liquid assisted grinding; NT: neat grinding, SDG: solvent drop-grinding; NR: not reported.