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Chemical Structure| 16415-12-6 Chemical Structure| 16415-12-6

Structure of 16415-12-6

Chemical Structure| 16415-12-6

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Xue, Wangyang ;

Abstract: This dissertation investigates the dynamic partitioning of surfactants into non-equilibrium emulsions, with a focus on understanding how these processes influence interfacial tension, phase behavior, and droplet wetting dynamics. Surfactant partitioning is a critical factor in stabilizing emulsions, where surfactant molecules migrate from the continuous aqueous phase to the dispersed oil phase, altering the interfacial properties. Traditional studies often rely on bulk two-phase equilibrium partitioning tests, which fail to capture the complexities of non-equilibrium conditions found in real-world emulsions. Here, we utilize a "single-droplet extraction" method to measure surfactant partitioning into oil microdroplets, providing a detailed understanding of these dynamic processes. Our experiments focus on the partitioning behavior of Tergitol NP-9, a nonionic surfactant, into tetrachloroethylene (TCE) and other oils, examining how droplet size and surfactant concentration influence the steady-state surfactant concentration within the oil phase. We found that partitioning is more pronounced in smaller droplets, with higher surface-area-to-volume ratios driving rapid cross-interface transport of surfactants. Larger droplets take longer to reach a steady state and exhibit lower partitioning coefficients, underscoring the importance of considering droplet size in surfactant dynamics. The results also indicate that non-equilibrium processes can lead to ultra-low interfacial tension and droplet deformation over time, phenomena not accounted for by equilibrium models. Additionally, we explore how surfactant partitioning affects wetting dynamics on solid substrates, particularly the unexpected dewetting behavior of oil droplets on hydrophobic surfaces in the presence of surfactants. This behavior, influenced by surfactant adsorption and partitioning, suggests that the surface tension at both the oil-water and solid-oil interfaces is highly dynamic and responsive to surfactant concentration and distribution. The findings challenge existing models of droplet wetting and motility, offering new insights into how surfactant partitioning can be tuned to engineer responsive, self-organizing emulsions with complex functionalities. This research advances our understanding of non-equilibrium surfactant partitioning and its critical role in emulsion stability and droplet behavior. The results have broad implications for industries that rely on emulsions, including pharmaceuticals, food science, and materials engineering, where optimizing emulsion stability is essential for product performance.

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Kueyoung E. Kim ; Wangyang Xue ; Lauren D. Zarzar ;

Abstract: Hypothesis Sessile droplets solubilizing in surfactant solution are frequently encountered in practice, but the factors governing their non-equilibrium dynamics are not well understood. Here, we investigate mechanisms by which solubilizing, sessile oil droplets in aqueous surfactant solution dewet from hydrophobic substrates and spread on hydrophilic substrates. Experiments We quantify the dependence of droplet contact line dynamics on drop size and oil, surfactant, and substrate chemistries. We consider halogenated oils as well as aromatic oils and focus on common nonionic nonylphenol ethoxylate . We correlate these results with measurements of the interfacial tensions. Findings Counter-intuitively, under a range of conditions, we observe complete dewetting of oil from hydrophobic substrates but spreading on hydrophilic substrates. The timescales needed to reach a steady-state contact angle vary widely, with some droplets examined taking over a day. We find that surfactant surface adsorption governs the contact angle on shorter timescales, while partitioning of surfactant from water to oil, and oil solubilization into the water, act on longer timescales to facilitate the complete dewetting. Understanding of the role played by surfactant and oil transport presents opportunities for tailoring sessile droplet behaviors and controlling droplet dynamics under conditions that would previously not have been considered.

Keywords: Wetting ; Surfactant ; Adsorption ; Partitioning ; Sessile Droplet

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Alternative Products

Product Details of [ 16415-12-6 ]

CAS No. :16415-12-6
Formula : C19H42O3Si
M.W : 346.62
SMILES Code : CO[Si](OC)(CCCCCCCCCCCCCCCC)OC
MDL No. :MFCD00069149
InChI Key :RSKGMYDENCAJEN-UHFFFAOYSA-N
Pubchem ID :85406

Safety of [ 16415-12-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 16415-12-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 23
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 18
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 104.57
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

27.69 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

5.71
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

8.59
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

6.35
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

3.36
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

4.88
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

5.78

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-6.21
Solubility 0.000212 mg/ml ; 0.000000613 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-9.05
Solubility 0.000000311 mg/ml ; 0.0000000009 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-6.79
Solubility 0.0000563 mg/ml ; 0.000000163 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-2.32 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

1.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

1.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<2.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

5.17

Application In Synthesis of [ 16415-12-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 16415-12-6 ]

[ 16415-12-6 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 5894-60-0 ]
  • [ 16415-12-6 ]
References: [1] Patent: US6150551, 2000, A, .
 

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