Paper page

Original: publisher page

Naila A. Mugheirbi, Laura I. Mosquera-Giraldo, Carlos H. Borca, Lyudmila V. Slipchenko, Lynne S. Taylor* · Molecular Pharmaceutics (ACS Just Accepted Manuscript, web 06 Jun 2018) (2018)

Phase Behavior of Drug-Hydroxypropyl Methylcellulose Amorphous Solid Dispersions Produced from Various Solvent Systems: Mechanistic Understanding of the Role of Polymer using Experimental and Theoretical Methods

Whether a spin-coated itraconazole–HPMC film comes out mixed or phase separated depends on the alcohol paired with dichloromethane and on the water the solvent picks up: water separates the drug with methanol and ethanol, but with n-propanol and n-butanol it is needed to keep HPMC dissolved and the film mixed.

Abbreviations

ITZ itraconazole; HPMC hydroxypropyl methylcellulose (METHOCEL E3); ASD amorphous solid dispersion; DCM dichloromethane; MeOH methanol; EtOH ethanol; IPA isopropanol; PrOH n-propanol; BuOH n-butanol; RH relative humidity; FLOM fluorescence optical microscopy; BF TEM bright-field transmission electron microscopy; AFM atomic force microscopy; LCR Lorentz contact resonance; nanoTA nanothermal analysis; DLS dynamic light scattering; TGA thermogravimetric analysis; MDSC modulated differential scanning calorimetry; PXRD powder X-ray diffraction; HSP Hansen solubility parameter; R0 interaction radius of the Hansen sphere; MD molecular dynamics; Rg radius of gyration; RDF radial distribution function; AAPS amorphous-amorphous phase separation; SI p. = page of the supporting information.

Graphical abstract: Folded HPMC gives a separated film, extended HPMC a mixed one
Graphical abstract · p.48 · Folded HPMC gives a separated film, extended HPMC a mixed oneShows. the authors' model: a folded HPMC chain leads to a phase-separated film, an extended chain to a miscible one.

Story. Why they did it → how → what they found → how it fits together → what is left. Each part opens with the short version; "More detail" under it gives the full account. Grey ids open the evidence behind a sentence.

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Question

How do the alcohol co-solvent and the water picked up during spin coating change the phase behavior of ITZ–HPMC dispersions, and what role does the state of HPMC in the solvent play?

Short answer

Water works both ways. MeOH and EtOH films made in humid air (50% RH, 21 °C) were phase separated, and EtOH films mixed at 20% RH; PrOH and BuOH films mixed in humid air but separated at 20% and 7% RH; IPA films were heterogeneous wet and dry, approaching homogeneity only at 50 °C and 50% RH. In drug-free solutions HPMC was present as single chains in MeOH and EtOH but aggregated in the higher alcohols unless water was present. ·····

Conclusion

For 30:70 ITZ:HPMC films spin coated from 50:50 alcohol:DCM, water "can be a double-edged sword": it caused drug–polymer demixing with MeOH and EtOH and was needed for mixed films with PrOH and BuOH. ·· The authors explain the lower-alcohol case by water concentrating as the solvent evaporates, since MeOH forms no azeotrope with water and EtOH concentrates water only above about 5% water, so that the poorly water-soluble drug separates into discrete domains ("anticipated"). · They explain the higher-alcohol case through the polymer: without water HPMC aggregates in PrOH, BuOH and IPA and gives network-like phase separation ("likely"), with water it stays as single chains, and their data "suggests" that HPMC must be present as discrete, extended chains to give an intimately mixed ASD. ··· IPA gave separated films wet and dry because both drug and polymer dissolve poorly in it ("likely"), and faster evaporation gave smaller domains ("suggesting"). ·· Three links were inferred rather than measured: the water content of the evaporating solutions, the composition of most domains, and the state of HPMC in the drug-containing solutions, for which the evidence comes from drug-free HPMC solutions, solubility-parameter calculations and simulations. ··

01Why this study

Known 1Phase separation undermines an ASD

Above the amorphous miscibility limit the drug forms drug-rich domains that can crystallize.

Zhang 2011, ref 6

Known 2Solvents can change phase behavior

A solubility gap between drug and polymer in the solvent should make phase behavior solvent dependent, but studies have mostly covered polymer blends.

Al-Obaidi 2009, ref 10; Paudel 2012, ref 8

Known 3ITZ–HPMC is a known problem case

Films from DCM:MeOH were phase separated at uncontrolled humidity, and the group traced this to water.

Purohit 2015, ref 12; Mugheirbi 2017, ref 13

Gap → this paperHow does the co-solvent change the polymer in solution, and through it the phase behavior of ITZ–HPMC films?
More detail

What was already known. The introduction and discussion build on these points:

  • Why ASDs and why phase separation matters. Amorphous drugs dissolve faster than crystals and can supersaturate, but tend to crystallize, so they are blended with a polymer (Simonelli 1976, ref 1; Rumondor 2009, ref 2; Caron 2013, ref 3). Stability depends on the crystalline solubility and amorphous miscibility of the drug in the polymer; above the miscibility limit, amorphous–amorphous phase separation (AAPS) gives drug-rich and polymer-rich phases, and crystallization in the drug-rich domains can erase the solubility gain (Sun 2010, ref 4; Serajuddin 1999, ref 5; Zhang 2011, ref 6). ·
  • Solvent effects on blends. Most phase-behavior studies make blends by solvent evaporation, but few look at how compatible the solvent is with the polymer; most such work concerns polymer–polymer blends (Bank 1971, ref 7; Paudel 2012, ref 8; Ansari 2008, ref 9). The large solubility gap between a drug and a polymer is expected to produce solvent-triggered phase behavior (Al-Obaidi 2009, ref 10), more complicated with multicomponent solvents (Wulsten 2009, ref 11), which are common in processing.
  • Low-resolution methods can miss separation. DSC and polarized light microscopy may overestimate miscibility (Paudel 2012, ref 8; Purohit 2015, ref 12); the group used high-resolution imaging instead (refs 13-15).
  • The ITZ–HPMC history. ITZ–HPMC made from DCM:MeOH at uncontrolled humidity was phase separated, with ITZ-rich discrete domains (Purohit 2015, ref 12); the group then linked this separation to water during production, found that MeOH films were miscible only at 7% RH, and that as little as 1% water in a DCM:MeOH spray solution caused separation (Mugheirbi 2017, ref 13). ···
  • Water in the solvent separates other ASDs too (Saboo 2017, ref 33; Rumondor 2011, ref 34).
  • Polymer conformation matters. Extended polymer conformations were reported to promote interaction with the drug and prevent crystallization (Mosquera-Giraldo 2016, ref 40); solvent composition sets the preferred conformation of hydrophilic polymers such as PEG (Liu 1969, ref 41) and hydration shells affect polymer conformation (Mochizuki 2017, ref 42). ·
  • Hansen solubility parameters give a sphere around each polymer; a solvent closer to its centre than the interaction radius R0 should dissolve it, and mixing solvents moves the blend's parameters by volume fraction (Hansen 1967, ref 17; Archer 1992, ref 18).

What the paper set out to do. Study how the initial solvent composition changes the conformation of HPMC and, through it, the phase behavior of ITZ–HPMC ASDs made by spin coating, using five alcohols (MeOH, EtOH, IPA, n-PrOH, n-BuOH) as co-solvents with DCM, high-resolution imaging, and supporting measurements and simulations of the polymer in the solvent.

02How they approached it

One drug–polymer pair at one ratio and one solvent ratio; only the alcohol changes, from methanol to n-butanol, and the films are made at high, low and very low humidity and at several temperatures. The polymer's state is followed separately in drug-free solutions, and solubility parameters and simulations are used to explain it. ····

ITZ:HPMC 30:70itraconazole with HPMC E3, w/wThe same in every film; 10 mg/mL total solids. Measured. ··
MeOHmethanol, a "lower alcohol"No azeotrope with water; 0.55 cP; calculated inside the HPMC solubility sphere. Films, DLS, evaporation and solubility measured; not simulated. ·
EtOHethanol, a "lower alcohol"Azeotrope at about 4.5–5% water; 1.19 cP; inside the sphere. Measured and simulated. ·
IPAisopropanol, a branched "higher alcohol"Azeotrope at 12.1% water; 2.27 cP; outside the sphere; lowest ITZ solubility. Measured and simulated. ··
PrOHn-propanol, a "higher alcohol"Azeotrope at 71.7% as printed; 2.2 cP; outside the sphere. Measured and simulated. ·
BuOHn-butanol, a "higher alcohol"Azeotrope at 55.5% as printed; 2.95 cP; farthest outside the sphere. Measured; not simulated. ·

What was done

Experiment

ITZ:HPMC in 50:50 alcohol:DCM→spin coated at 50% RH, 21–50 °C, two spin speeds→FLOM and BF TEM.·····

Experiment

Same solutions spin coated at 21 °C, 20% and 7% RH→FLOM and BF TEM; one IPA film by AFM-LCR and nanoTA.··

↓
Experiment

Pure solvent mixtures, dry or with 4% or 10% water→TGA evaporation profiles at 24 °C.·

Experiment

Crystalline ITZ in each pure alcohol→clear and cloud points→PXRD and MDSC of the precipitates.····

↓
Experiment

Drug-free HPMC solutions before and after dry or humid evaporation→DLS sizes→AFM of spin-coated HPMC films.···

Calculation

Hansen distances of HPMC to each alcohol and to alcohol–water mixtures.··

Model

MD of one or four HPMC chains in alcohol:DCM with or without water→Rg and RDF.·····

↓
Comparison

Film outcome set against solvent evaporation, polymer state and calculated compatibility→summary of drug and polymer compatibility with each solvent, dry and wet (Fig. 14).·

More detail

What was done

  1. Solutions and films. ITZ and HPMC (30:70 w/w) were dissolved at 10 mg/mL in 50:50 v/v alcohol:DCM. 100 µL was spin coated (500 rpm for 3 s, then 2000 rpm for 30 s) onto quartz or carbon-coated TEM grids at 50 ± 5% RH, with a heat lamp setting the sample zone to 21, 30, 35, 40 or 50 °C; a slower protocol (500 rpm for 15 s twice) tested evaporation rate. Films were stored under vacuum for at least 24 h. Films were also made at 21 °C and 20% RH (all alcohols) and 7% RH (IPA, PrOH, BuOH); how the low RH was set is not described. ····
  2. Film imaging. Fluorescence microscopy (ITZ is autofluorescent; excitation 330–380 nm) screened for phase separation; bright-field TEM resolved smaller domains. One IPA film made at 20% RH was mapped by AFM with Lorentz contact resonance at 130 kHz, which separates stiffer and softer regions, and by local nanothermal analysis of the softening temperature of each region. ···
  3. Evaporation. About 50 µL of each pure solvent mixture, dry or with 4% water (10% for EtOH as well), was evaporated in a TGA pan at 24 °C under nitrogen, and weight and its time derivative were recorded every minute.
  4. Drug solubility. Crystalline ITZ slurries (1–5.5 mg/mL) in each pure alcohol were heated at 0.5 °C/min until clear and cooled at 0.5 °C/min to 10 °C until cloudy; the precipitate was examined by PXRD and modulated DSC. ··
  5. Polymer in solution and film. Drug-free HPMC (7 mg/mL, the HPMC concentration of the stock solutions) in 1:1 DCM:alcohol was evaporated to about half volume under nitrogen or at 50% RH and sized by DLS (species below 10 nm counted as single chains, above 10 nm as aggregates); the same solutions were spin coated dry or at 50% RH and imaged by AFM. ··
  6. Solubility parameters. Hansen distances between HPMC (literature parameters) and each alcohol, and alcohol–water mixtures from 0 to 100% water, were compared with the HPMC interaction radius R0 = 7.6 MPa^1/2. ··
  7. Simulations. A 20-monomer HPMC chain whose 60 substitution sites mimic HPMC E3 was simulated (GROMACS, CHARMM, 294 K, 20 ns production) in EtOH, PrOH or IPA with DCM at 50, 70 and 100% alcohol, and four chains with and without 15% water (55:30:15 alcohol:DCM:water); Rg and polymer–solvent RDFs were analysed, and backbone torsion barriers were scanned on 19 dimers. ···

Key equations

Total solubility parameter (Eq. 1)
δ=(δdi2+δpi2+δhi2)1/2

The total Hansen parameter combines dispersion, polar and hydrogen-bonding parts; for HPMC it is the centre of the solubility sphere.

Mixing rule (Eq. 2)
δmixture=Φ1δ1+Φ2δ2+⋯

A solvent blend takes the volume-fraction average of its components' parameters; this is how water moves an alcohol toward HPMC in Fig. 9b.·

Hansen distance (Eq. 3)
Rps=(4(δp−δs)di2+(δp−δs)pi2+(δp−δs)hi2)1/2

The distance between polymer p and solvent s in parameter space, with the dispersion term counted four times; a distance below R0 means the solvent is expected to dissolve the polymer. (The paper prints the outer bracket as square brackets.)·

Radius of gyration (Eq. 4)
Rg2≡∑iNmi(r→i−r→COM)2∑iNmi

The mass-weighted spread of the chain's atoms around its centre of mass; a larger Rg means a more extended chain.·

Terms used on this page
  • Azeotrope: a liquid mixture that evaporates without changing composition; an alcohol–water mixture on the alcohol-rich side of it loses water no faster than alcohol.
  • Hansen sphere and R0: the region of solubility-parameter space around a polymer within which solvents dissolve it; R0 is its radius.
  • Spinodal-like microstructure: an interconnected, worm-like pattern typical of spontaneous phase separation, as opposed to discrete round domains.
  • Lorentz contact resonance (LCR): an AFM mode in which stiffer regions resonate at a higher frequency, so driving at one frequency highlights one component.
  • Radius of gyration (Rg): a size measure of a polymer chain; radial distribution function (RDF): the relative likelihood of finding solvent atoms at a given distance from the polymer, 1 being the bulk value.
  • % intensity (DLS): the share of scattered light from a population; large aggregates scatter far more than single chains, so it is not a mass fraction.
  • Clear point and cloud point: the temperatures at which a slurry fully dissolves on heating and turns turbid on cooling.

03Main findings

1

With methanol and ethanol, humid air separates the drug

At 50% RH, MeOH and EtOH films showed discrete drug domains at 21 °C. At 20% RH EtOH films were homogeneous while MeOH films stayed separated; MeOH needed 7% RH in the group's earlier work. ···

See also Fig. 3

Fig. 2: Fluorescence images of films from five alcohols at five temperatures, 50% RH
Fig. 2 · p.17 · Fluorescence images of films from five alcohols at five temperatures, 50% RHShows. bright domains for MeOH, EtOH and IPA at 21 °C, shrinking with temperature; PrOH and BuOH dark and uniform throughout.Read it as. bright spots = concentrated ITZ fluorescence (drug domains); uniform dark = homogeneous film.Also supports F2, F4, K1, K2, K5
Fig. 4: Fluorescence and TEM of films made at 20% and 7% RH
Fig. 4 · p.21 · Fluorescence and TEM of films made at 20% and 7% RHShows. MeOH still separated, EtOH homogeneous at 20% RH (top row); IPA, PrOH and BuOH heterogeneous at 20% and 7% RH, with network-like TEM textures for PrOH and BuOH at 7%.Also supports F2, K1, K2
More detail

At 21 °C and 50% RH, fluorescence microscopy showed bright, high-intensity regions (ITZ is autofluorescent) in MeOH and EtOH films, which the authors read as a non-uniform drug distribution. ·· In TEM, MeOH films had a few large ring-shaped domains on an interconnected two-tone background, which the authors call a second form of phase separation in the continuous phase; EtOH films had many round discrete domains of widely varying size on a uniform background. · Earlier work identified such discrete domains in DCM:MeOH films as ITZ-rich. At 20% RH and 21 °C, MeOH films still showed many small discrete domains, while EtOH films were featureless in both fluorescence and TEM, which the authors take as a miscible system. ·· MeOH films became miscible only at 7% RH in the earlier study. The authors conclude that with the lower alcohols dry conditions were necessary for intimate mixing.

2

With n-propanol and n-butanol, humid air is needed for a mixed film

At 50% RH, PrOH and BuOH films looked homogeneous at all five temperatures, and a BuOH film was featureless in TEM. At 20% and 7% RH they were phase separated, with network-like textures. ··

See also Fig. 2, Fig. 4

More detail

In fluorescence, PrOH and BuOH films made at 50% RH were dark and uniform from 21 to 50 °C, and the TEM image of a BuOH film made at 21 °C was featureless, "confirming miscibility" in the authors' words; no TEM of a PrOH film at 50% RH is shown. ···· At 20% RH both gave mottled fluorescence and heterogeneous TEM images, and at 7% RH TEM showed network-like dark and light regions. ··· The authors call the separation at low humidity "somewhat surprising" and "counterintuitive", since MeOH films became miscible at 7% RH.

3

Isopropanol films are heterogeneous wet and dry

At 50% RH, IPA films had discrete domains at 21–30 °C that were gone by 50 °C, on a fine textured background; at 20% and 7% RH they were heterogeneous without discrete domains. In a film made at 20% RH, raised features softened at about 115 °C and the surrounding phase at about 60 °C, read as HPMC-rich and ITZ-rich. ····

More detail

In TEM, IPA films made at 50% RH showed dark discrete domains on a fine worm-like background at 21 °C, fewer and smaller ones at 30 °C, few on a mottled background at 35 °C and none at 50 °C. In fluorescence, films made above 30 °C had no discrete domains but an inhomogeneous pattern that the authors liken to spinodal decomposition. · At 20% and 7% RH, IPA films were heterogeneous without discrete domains. · The AFM map of the 20% RH film showed an uneven surface with protruding features in a semi-continuous arrangement. Contact-resonance spectra peaked at about 129.3 kHz for one phase and 130.0 kHz for the other, and nanothermal analysis gave softening at about 115 °C for the raised features (the plotted trace drops at about 111 °C) and about 60 °C for the surrounding phase. The authors take the raised features to be HPMC-rich and the continuous phase ITZ-rich, consistent with the glass transitions of HPMC and ITZ. They read the network at 20% RH as polymer incompatibility with the solvent ("suggests") and the discrete domains at higher humidity as "likely" drug-rich, because ITZ is least soluble in IPA and water lowers its solubility further; the composition of those domains was not measured. ··

Fig. 3: TEM of films made at 50% RH
Fig. 3 · p.19 · TEM of films made at 50% RHShows. MeOH and EtOH domains shrinking from 21 to 50 °C; featureless BuOH; IPA domains on a worm-like background disappearing from 21 to 50 °C.Also supports F1, F4
Fig. 5: AFM, contact-resonance and nanothermal analysis of an IPA film made at 20% RH
Fig. 5 · p.22 · AFM, contact-resonance and nanothermal analysis of an IPA film made at 20% RHShows. raised features (a) dark in the 130 kHz map (b); spectra (c); 3D view (d); softening near 111–115 °C for the raised features and about 60 °C for the matrix (e).Also supports K7
4

Faster evaporation gives smaller domains

Domains shrank as the spin-coating temperature rose from 21 to 50 °C (MeOH, EtOH, IPA), and slower spinning kept larger domains in DCM:MeOH films at every temperature. Sizes were judged from images, not measured. ···

See also Fig. 2, Fig. 3

More detail

In fluorescence, MeOH films went from coarse domains at 21 °C to fine dots at 30–40 °C and an almost uniform film at 50 °C; EtOH films kept dense domains to 40 °C and were uniform at 50 °C. · TEM showed the same shrinkage for MeOH, EtOH and IPA. ·· With the slower 500 rpm protocol, DCM:MeOH films kept visible domains up to 50 °C. The authors conclude that the smaller domains at higher temperature arise "mainly" from faster evaporation ("suggesting"); the evaporation rate of the films was not measured. ·

Fig. S1: Slower spinning keeps larger domains
Fig. S1 · p.SI-2 · Slower spinning keeps larger domainsShows. DCM:MeOH films at 2000 rpm (left) lose their domains by 50 °C; at 500 rpm (right) domains remain at every temperature.Also supports K5
5

Water slows the evaporation of the methanol blend, not of the higher-alcohol blends

With 4% water, DCM:MeOH took about 40 min instead of about 12 (text: 4-fold). DCM:EtOH was unchanged at 4% but took about 73 min at 10% (text: 7-fold). DCM:IPA was 2.5 min slower; DCM:PrOH and DCM:BuOH were unchanged. These are pure solvents at 24 °C. ··

Fig. 6: Evaporation of the solvent mixtures with and without water
Fig. 6 · p.25 · Evaporation of the solvent mixtures with and without waterShows. 4% water stretches DCM:MeOH evaporation from about 12 to 40 min and 10% water stretches DCM:EtOH to about 73 min; PrOH and BuOH blends are unchanged.Also supports K3
More detail

Dry DCM:MeOH evaporated in about 12 min with a biphasic, steadily slowing rate; with 4% water it started at a similar rate but then slowed, finishing at about 40 min with a small rate spike just before the end. · DCM:EtOH evaporated in about 13.5 min dry and about 11.5 min with 4% water; with 10% water it took about 73 min, again with a late spike. DCM:IPA took about 10.7 min dry and 13 min with 4% water (text: 2.5 min delay), with unchanged profile shapes. · DCM:PrOH (about 27 min) and DCM:BuOH (about 55–60 min) were unaffected by 4% water. The plotted fold changes are smaller than the stated 4-fold and 7-fold (about 3.3 and 5.4). The authors take this as support for their azeotrope argument (F1, F2): water concentrates as DCM:MeOH evaporates but not in the higher-alcohol blends. · The TGA runs used solvents without drug or polymer; the stock-solution runs mentioned in the methods are not shown.

6

HPMC aggregates in the higher alcohols unless water is present

In drug-free starting solutions HPMC chains measured about 4–5 nm in all five blends, but IPA, PrOH and BuOH also held aggregates of about 43–53 nm. After dry evaporation every solution aggregated; after evaporation at 50% RH the PrOH and BuOH aggregates were gone, while IPA aggregates grew to about 117 nm. Smooth HPMC films formed where single chains dominated. ··

Fig. 7: HPMC single chains (top) and aggregates (bottom) by DLS
Fig. 7 · p.28 · HPMC single chains (top) and aggregates (bottom) by DLSShows. bars = hydrodynamic diameter, triangles = % intensity; arrows = species absent. Aggregates in the IPA, PrOH and BuOH starting solutions and after dry evaporation; none in PrOH and BuOH after humid evaporation.Also supports K4
More detail

In the starting solutions MeOH and EtOH showed only single chains (about 3.9 and 4.9 nm), while IPA, PrOH and BuOH showed single chains plus aggregates of about 52, 45 and 43 nm carrying about 66–74% of the scattered intensity. ···· After evaporation to half volume under nitrogen, aggregates appeared in MeOH (about 36 nm, 17 ± 4% intensity) and EtOH (about 16 nm, 11 ± 5%), and single chains vanished from IPA, PrOH and BuOH, which held only aggregates of about 74–80 nm. ···· After evaporation at 50% RH, MeOH, PrOH and BuOH held single chains only, EtOH a few ~20 nm aggregates (6 ± 4%), and IPA only aggregates of about 117 nm. ···· Drug-free HPMC films were smooth from MeOH and EtOH (dry and wet) and from PrOH and BuOH (wet), and rough and corrugated from IPA (dry and wet) and from PrOH and BuOH (dry). The authors match film texture to solution state ("could be rationalized") and conclude that water was necessary to dissolve HPMC in the PrOH and BuOH systems. · The percentages are scattering intensities, and the solutions contained no drug. ·

Fig. 8: HPMC state in solution and texture of drug-free HPMC films, dry versus 50% RH
Fig. 8 · p.30 · HPMC state in solution and texture of drug-free HPMC films, dry versus 50% RHShows. smooth films where the solution held single chains (green), rough films where it held aggregates (red).Also supports K4
7

Solubility parameters place methanol and ethanol inside the HPMC sphere and the higher alcohols outside, unless water is added

Calculated Hansen distances were about 6.7 (MeOH) and 6.9 (EtOH), inside R0 = 7.6 MPa^1/2, and about 8.8 (PrOH), 9.8 (IPA) and 10.25 (BuOH), outside. Adding water brings them inside: the first plotted water content below R0 is 20% for PrOH and 40% for IPA and BuOH. ···

Fig. 9: Hansen distances between HPMC and the alcohols, without and with water
Fig. 9 · p.32 · Hansen distances between HPMC and the alcohols, without and with waterShows. (a) MeOH and EtOH below R0, the higher alcohols above; (b) distances falling below R0 as water is added.Also supports K6
More detail

With the literature HPMC parameters (δd 17.4, δp 14.9, δh 19.3 MPa^1/2; R0 7.6) the distance rose from MeOH and EtOH (inside the sphere) to PrOH, IPA and BuOH (outside); the authors read this as HPMC solubility falling with chain length and with branching ("clearly indicating"), while noting that solubility parameters cannot predict solubility quantitatively. ··· As water was added in 10% steps, the distances to IPA, PrOH and BuOH fell steadily, reaching about 7.50 for PrOH at 20% water and about 7.03 and 7.38 for IPA and BuOH at 40%, and converging at about 4.52 for pure water; the authors expect HPMC to be more soluble in alcohols containing water. · The parameters used for the alcohols and water are not printed, and the plot axis is in % w/w while the mixing rule uses volume fractions.

8

In simulations, water forms the first solvent shell around HPMC and expands it in n-propanol

A single HPMC chain had its smallest average Rg at 50:50 alcohol:DCM (about 1.92–2.15 nm) and larger values with more alcohol (up to about 2.39 nm), while each run spanned about 1.2 nm. With 15% water, water formed the closest shells, and the Rg of four chains rose in PrOH (about 2.17 → 2.33 nm) but barely in EtOH and not in IPA. ···

Fig. 11: Size of four HPMC chains with and without water
Fig. 11 · p.35 · Size of four HPMC chains with and without waterShows. Rg rises with water in PrOH, barely in EtOH, not in IPA.Also supports K8
More detail

The average Rg of one chain was about 1.92, 2.30 and 2.07 nm in EtOH at 50, 70 and 100% alcohol, 2.14, 2.22 and 2.25 nm in PrOH, and 2.15, 2.35 and 2.39 nm in IPA; each run spanned about 1.4–2.9 nm. The authors read the rise with alcohol as a more extended conformation that "may be favored" in alcohols. With 55:30:15 alcohol:DCM:water, water shells formed at about 0.41 and 0.78 nm with peak heights of about 1.18 (EtOH) and 1.35–1.36 (PrOH, IPA), above the alcohol and DCM curves. · The four-chain Rg went from about 2.17 to 2.33 nm in PrOH, 2.15 to 2.20 nm in EtOH, and stayed at about 2.18 nm in IPA; the authors say the polymer "clearly expands" in PrOH. · The boxes overlap, the differences are small against the spread, and MeOH and BuOH were not simulated. ·

Fig. 10: Size of one HPMC chain versus alcohol proportion
Fig. 10 · p.34 · Size of one HPMC chain versus alcohol proportionShows. smallest average Rg at 50% alcohol for EtOH, PrOH and IPA; wide range within each run.
Fig. 13: Water forms the first solvent shell around HPMC
Fig. 13 · p.37 · Water forms the first solvent shell around HPMCShows. HPMC–water RDF peaks (black) above the alcohol and DCM curves in all three alcohols.Also supports K8

04Further observations

  • Crystalline ITZ dissolves least in IPA and most in MeOH: 3 mg/mL clears at about 49 °C in MeOH and 68 °C in IPA. ·
  • Precipitates from cooled ITZ solutions are mostly amorphous; only the BuOH one lacks Bragg peaks. ·
  • At 50:50 alcohol:DCM, alcohol is more likely than DCM next to HPMC; at 70:30 both are equally likely. ·
  • The HPMC backbone torsion barrier is about 7 kcal/mol, judged moderately weak. ·
  • All drug–polymer solutions looked clear, although the drug-free HPMC solutions held aggregates. ··
More detail
  • ITZ solubility in the pure alcohols. Clear points (crystalline solubility) rose with concentration in every alcohol: 1 mg/mL cleared at about 37.5 °C in MeOH, 39 °C in PrOH, 46 °C in EtOH, 48 °C in BuOH and 53 °C in IPA, and 3 mg/mL at about 49, 56, 60, 60 and 68 °C. On cooling, turbidity appeared at much lower temperatures (for example 5.5 mg/mL clouded at about 26–34 °C in MeOH, EtOH, PrOH and BuOH), and IPA clouded at much lower concentrations (1.5–3 mg/mL at about 20–31 °C). ·
  • Nature of the precipitates. PXRD showed an amorphous halo with sharp peaks for MeOH, EtOH, IPA and PrOH precipitates and a halo only for BuOH. MDSC traces carry guides at about 60, 73 and 90 °C, the glass transition and two liquid-crystalline transitions of glassy ITZ, which the authors assign to the higher-alcohol precipitates, and a melting endotherm to the lower-alcohol ones; in the plot, all five traces show a large endotherm near 160–170 °C. ··
  • Where alcohol and DCM sit. The polymer–solvent RDF showed two solvation layers at about 0.55 and 0.95 nm. At 70:30 alcohol:DCM the alcohol and DCM curves coincide; at 50:50 the alcohol curve rises (about 0.88 at the first layer) and the DCM curve falls (about 0.71). The authors suggest the solvation shell, and with it Rg, changes continuously as the ratio shifts during evaporation ("may imply"). ··
  • Chain flexibility. Rigid torsion scans of 19 HPMC dimers gave an average barrier of about 7 kcal/mol; the average curve ran from about 0.7 to 6.0 kcal/mol and single dimers reached about 11 kcal/mol. The authors judge such barriers moderately weak at about 300 K, so they "may have limited impact" on sampling. ·
  • Clear solutions can hide aggregates. All drug–polymer stock solutions were visually transparent, yet the drug-free HPMC solutions with the higher alcohols contained aggregates, a solvophobic behavior the authors hold responsible for the rough HPMC films made under dry conditions. ··
  • Viscosity. Literature viscosities at 20 °C rise from 0.55 cP (MeOH) to 2.95 cP (BuOH); the authors expect the more viscous higher alcohols to slow diffusion of drug into drug-rich domains, which was not tested. ·
Fig. S2: ITZ clear and cloud points in the pure alcohols
Fig. S2 · p.SI-3 · ITZ clear and cloud points in the pure alcoholsShows. lowest solubility in IPA, highest in MeOH on heating; cloud points far below clear points.

05How the authors connect the findings

1During spin coating the hygroscopic alcohols take up water from the air, more at higher humidity. ·
↓
2As the solvent evaporates, the alcohol's azeotrope with water decides whether water or alcohol is left concentrated. ··
↓
MeOH, or EtOH with much waterNo azeotrope, or water above it↓water concentrates as the alcohol leaves↓the poorly water-soluble ITZ separates↓discrete drug-rich domains, larger when evaporation is slow.··
EtOH at low humidity; PrOH or BuOH with waterThe azeotrope holds↓alcohol, not water, concentrates; water keeps HPMC as single extended chains↓intimately mixed film.···
PrOH or BuOH dry; IPA alwaysHPMC is incompatible with the alcohol↓HPMC aggregates in the solution↓network-like, corrugated phase separation; with IPA and water, drug-rich domains as well.····
What sets the switch point. Which component the remaining solvent cannot hold: water-enriched solvent rejects ITZ, dry higher alcohols reject HPMC (Fig. 14). ·
Conclusion drawn. Water "can be a double-edged sword"; HPMC "needs to exist as discrete molecules in the extended conformation" for a mixed ASD (their data "suggests"). ·
Fig. 14: Which component the solvent can hold, dry and wet
Fig. 14 · p.42 · Which component the solvent can hold, dry and wetShows. ticks and crosses for HPMC and ITZ compatibility with each solvent system; only MeOH and EtOH dry and PrOH and BuOH wet tick both.
More detail
  1. MeOH and EtOH are hygroscopic and take up water from the air during spin coating; less water is "expected" at 20% than at 50% RH. For EtOH at 20% RH the authors state an equilibrium water content below 3% by volume, just under the 95:5 v/v azeotrope.
  2. An azeotropic mixture evaporates as one component. An EtOH-rich solution below the azeotrope leaves an EtOH-rich residue, so water does not concentrate; above about 5% water, water concentrates. MeOH has no azeotrope, evaporates faster than water ("anticipated"), and water concentrates. PrOH and BuOH form azeotropes at high water contents, so their solutions concentrate in alcohol, not water ("likely" why water did not change their evaporation time). The authors note that DCM and the dissolved solutes, whose effect on the azeotropes is unknown, are ignored. ····

[-] Water concentrates (MeOH; EtOH at 50% RH). With ITZ's low aqueous solubility, discrete drug domains are "anticipated" when water concentrates and evaporation is slow; this framework "largely" rationalizes the films. MeOH therefore needs very low humidity (7% RH). The slowed evaporation of DCM:MeOH with 4% water and of DCM:EtOH with 10% water is offered as support. ··

[+] Alcohol concentrates and HPMC stays dissolved (EtOH at 20% RH; PrOH and BuOH at 50% RH). Water was "necessary" to dissolve HPMC in PrOH and BuOH, judged from the separated films at low humidity, the dry-evaporation aggregation and the dry film texture; water is "anticipated" to keep HPMC as single chains in the preferred extended conformation, and extended conformations were reported to promote drug–polymer interaction and prevent crystallization (ref 40). The MD water shell and the larger Rg of HPMC with water in PrOH are offered as support ("suggests", "appeared"). ··

[-] HPMC aggregates (PrOH and BuOH dry; IPA). HPMC is solvophobic in the higher alcohols and aggregates even in clear solutions; the network-like corrugations are "likely" caused by solvent incompatibility with HPMC, while discrete domains and spinodal-like textures "seem" to come from drug–water incompatibility. IPA combines both: the polymer dissolves poorly in it wet or dry, and ITZ is least soluble in it and loses solubility further with water, so its discrete domains are "likely" drug-rich. ···

What sets the switch point. Fig. 14 summarises the authors' reading: under dry conditions HPMC is compatible with MeOH and EtOH only and ITZ with all alcohols except IPA; under wet conditions ITZ is incompatible with MeOH, EtOH and IPA and HPMC compatible with all except IPA. Only the combination where both are compatible (MeOH and EtOH dry, PrOH and BuOH wet) gives a mixed film. Viscosity is offered as an extra factor: the more viscous higher alcohols are "expected" to slow diffusion into drug-rich domains. ·

Conclusion drawn. Abstract: water-induced mixing with PrOH and BuOH is "due to the improved solubility of HPMC"; discussion: the data "suggests" HPMC needs to exist as discrete, extended molecules, and water "can be a double-edged sword". ··

06What it means for formulation

Stated by the authors
  • Screen solvents thoroughly before making an ASD by solvent evaporation such as spray drying.
  • With DCM:MeOH, ITZ–HPMC must be made at very low humidity (7% RH).
AI reading, not stated in the paper
  • For HPMC dispersions made from DCM and an alcohol, the right water level depends on the alcohol: keep water low with methanol or ethanol, but allow some with n-propanol or n-butanol.
  • A clear spray solution does not prove the polymer is dissolved as single chains; a light-scattering check of the solution is cheap.
More detail
Stated by the authors
  • The solvent-triggered phase behavior "highlights the importance of conducting a thorough screening of various solvents" before preparing ASDs by solvent evaporation, such as spray drying; the observations "may help in the rational design" of such ASDs. Spray drying itself was not tested here.
  • MeOH-based ITZ–HPMC ASDs have to be prepared at very low humidity (7% RH) to keep water in the solvent low.
  • Most HPMC grades are not soluble in single organic solvents, so multicomponent solvents, and with them these water effects, are hard to avoid.
AI reading, not stated in the paper
  • Water picked up from the air or present in the solvent is a process variable for HPMC dispersions, and its effect reverses between alcohols: a humidity or water specification set for a methanol process may be wrong for an n-propanol process.
  • Faster evaporation (higher temperature, faster spinning) shrank the domains in these films; in spray drying, where evaporation is much faster, the same chemistry may give finer separation that low-resolution methods can miss.
  • Visual clarity of the feed solution is not enough; the polymer can already be aggregated in a clear solution.
  • These results cover one drug, one polymer grade and one drug loading; how far they transfer to other drug–cellulose pairs is open.

07Open questions

Raised by the authors
  • How do the polymer's solvation shell and conformation change during evaporation as the alcohol:DCM ratio shifts?
  • How do DCM and the dissolved solutes change the azeotropic compositions?
Not covered by this paper (AI reading)
  • The water content of the evaporating solutions was never measured.
  • The polymer state was measured without drug.
More detail
Raised by the authors
  • Film miscibility should depend on the polymer conformation in the initial mixture and on its changes as the solvent composition shifts during evaporation; this was inferred from MD of fixed compositions only.
  • The azeotrope analysis ignores the effect of DCM and of the dissolved drug and polymer, which are "unknown factors".
  • The water shell around HPMC "could have important implications" for chain conformation and for drug–polymer phase separation.
Not covered by this paper (AI reading)
  • The water content of the solutions during and after spin coating, central to the azeotrope argument, was not measured, and how 20% and 7% RH were set is not described.
  • HPMC size and aggregation were measured only in drug-free solutions, and chain conformation only in simulations.
  • The composition of the discrete domains formed with EtOH and IPA, and of the network-like phases with PrOH and BuOH, was not measured.
  • Domain sizes and film evaporation rates were not quantified.
  • Only one drug loading (30%), one HPMC grade and spin-coated films were studied; spray drying, other loadings, stability and dissolution were not tested.

08How solid

AI assessment, not a statement made in the paper
Moderate

The film results are systematic across five alcohols, three humidities and five temperatures and are seen by two imaging methods. The explanation, water concentrating or HPMC aggregating, is inferred: water contents were not measured, the polymer was studied without drug, and the simulation effects are small. ····

More detail
What holds
  • The humidity reversal between lower and higher alcohols is seen in fluorescence and TEM for several films. ··
  • Water slowing DCM:MeOH but not DCM:PrOH or DCM:BuOH evaporation is directly measured.
  • HPMC aggregation in the higher alcohols and its removal by humid evaporation for PrOH and BuOH are measured by DLS and match the HPMC film textures. ·
  • The calculated solubility parameters point the same way as the DLS results. ·
What weakens it
  • The water content of the evaporating solutions is never measured, and the RH control at 20% and 7% is not described.
  • The polymer state is measured without drug, and the DLS percentages are scattering intensities. ·
  • Domain composition is measured for only one film, which has no discrete domains; the drug-rich identity of the discrete domains rests on earlier work.
  • Domain size and film evaporation rate are judged from images and pure-solvent TGA only.
  • The MD differences are small against the spread, cover three alcohols, and use molar compositions at 294 K. ·
  • Several cross-references and labels are wrong (Fig. 5 caption, cloud-point figure, dry = 20% RH in Fig. 8), and the stated fold changes in evaporation time exceed the plotted ones. ···
  • The DSC text and figure disagree on which precipitates show melting.

09Figure guide

Every figure and table of the paper, what it is there for, and what to check on the original. Key figures are shown with the story.

FigureWhat it does in the paperSupportsCheck (AI note)
Fig. 1 (p.12)Introduces the Hansen solubility sphere and the R0 criterion used in Fig. 9.0.2A schematic, not data.
Table 1 (p.14-15)Defines the substitution pattern of the 20-monomer HPMC model chain.0.2Percentages are site fractions of 60 sites.
Fig. 2 (p.17)key figureMain screen: phase state of films from five alcohols at five temperatures, 50% RH.F1, F2, F4Viscosity arrow order differs from printed viscosities.
Fig. 3 (p.19)key figureTEM of the clearest separated films plus BuOH at 50% RH; domains shrink with temperature.F1, F3, F4No PrOH image at 50% RH.
Fig. 4 (p.21)key figureLow-humidity films: EtOH mixes, PrOH and BuOH separate.F1, F2How 20% and 7% RH were set is not described.
Fig. 5 (p.22-23)key figureMaps phases in an IPA film: HPMC-rich raised features in an ITZ-rich matrix.F3Caption points to Fig. 4a, which is the MeOH film.
Fig. 6 (p.25-26)key figureWater slows evaporation of DCM:MeOH strongly, DCM:EtOH only at 10%, higher alcohols not at all.F5Stated fold changes exceed plotted ones.
Fig. 7 (p.28-29)key figureHPMC single chains versus aggregates in each solvent, before and after dry or humid evaporation.F6% intensity, drug-free solutions.·
Fig. 8 (p.30)key figureLinks HPMC solution state to the texture of HPMC films.F6Caption calls dry 20% RH; methods use nitrogen.
Fig. 9 (p.32-33)key figureHansen distances of HPMC to each alcohol and to alcohol–water mixtures.·F7R0 line drawn at about 7.75 in (a); % w/w axis versus volume mixing.·
Fig. 10 (p.34)key figureRg of one HPMC chain versus alcohol proportion.F8Small differences against the spread.
Fig. 11 (p.35)key figureRg of four chains with and without water.F8Overlapping boxes.
Fig. 12 (p.36)RDF of HPMC with alcohol and DCM at three compositions.0.4
Fig. 13 (p.37)key figureRDF with water: water forms the first shell.F8
Fig. 14 (p.42)key figureSummary of drug and polymer compatibility with each solvent, dry and wet.0.5A schematic, not data.
Graphical abstract (p.48)The authors' folded-versus-extended HPMC model.headerA schematic, not data.
More detail
FigureWhat it does in the paperSupportsCheck (AI note)
Fig. S1 (SI p.2)key figureSpin-speed test: slower spinning keeps larger domains.F4MeOH only; sizes not measured.
Figs. S2–S4 (SI p.3-5)key figureITZ clear and cloud points and the PXRD and MDSC of the precipitates.···0.4Text cites the cloud points as Fig. 7b; DSC text and plot disagree.·
Figs. S5–S6 (SI p.6)Backbone torsion energies of 19 HPMC dimers.0.4