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Structure of 162881-26-7

Chemical Structure| 162881-26-7

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Balcerak-Woźniak, Alicja ; Kabatc-Borcz, Janina ;

Abstract: This study reports novel diphenyliodonium tosylates (IODs) as highly effective photoinitiators for the radical polymerization of (meth)acrylates. The proposed compounds showed high photoinitiation efficiency in the polymerization process as one-component, as well as in two-component and threecomponent systems. The synthesized and developed derivatives were characterized by the presence of a nitro group attached to one of the phenyl rings, while the second aromatic ring was substituted by one of the halogen atoms (i.e. Br, Cl, F, and I). The introduction of two different electron withdrawing substituents into the chemical structure of iodonium salts is a new and unique approach in the design of novel asymmetrical IOD derivatives. The use of the proposed IODs as UV photoinitiators resulted in about 30% conversion of acrylate. The introduction of camphorquinone (CQ) to polymerizable compositions caused a shift in the absorption band of the photoinitiators and expanded the photoactivity of IODs to visible light. The proposed diphenyliodonium salts in combination with a light absorber (CQ) were highly active photoinitiators for radical polymerization upon LED illumination (conversion of about 30%–70%). The newly synthesized compounds can be promising alternatives to typical commercially available iodonium salt initiators (or co-initiators), which are commonly used in photopolymerization reactions.

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Yu-Chung Chang ; Lin Shao ; Wangcheng Liu ; Brian J. Bliss ; Baoming Zhao ; Zihui Zhao , et al.

Abstract: In additive manufacturing/3D printing, the limitation no longer lies in people’s imagination but in the materials that one can print with. While the additive manufacturing process can virtually create any geometry, available applications are often limited by factors like parts’ mechanical strength, glass transition temperature, and heat deflection temperature. These factors are especially critical for polymer-based printing. Here we introduce a simple formulation derived from the aminolysis of polylactic acid (PLA) plastic waste, namely the N-lactoyl ethanolamine (N-LEA). The N-LEA is next reacted with excess methacrylic anhydride, forming a photo-crosslinkable resin for MSLA 3D printing. The resulting 3D printed part has a set of impressive properties that is unrivaled amongst engineering grade 3D printing on the market and literature. The 3D printed part has an ultrahigh tensile strength of 131.7 , glass transition at ∼190 °C, and heat deflection temperature at 162.6 °C. This work demonstrates a true upcycling approach for turning PLA waste into a value-added product in a simple and efficient manner while also expanding the high-performance material portfolio available for photocuring additive manufacturing.

Keywords: Additive manufacturing ; 3D printing ; Photocurable resin ; Masked stereolithography ; PLA upcycling

Purchased from AmBeed:

Shiwei Han ; Valentin A. Bobrin ; Maxime Michelas ; Craig J. Hawker ; Cyrille Boyer ;

Abstract: The development of renewable vinyl-based photopolymer resins offers a promising solution to reducing the environmental impact associated with 3D printed materials. This study introduces a bifunctional lipoate cross-linker containing a dynamic disulfide bond, which is combined with acrylic monomers (n-butyl acrylate) and conventional photoinitiators to develop photopolymer resins that are compatible with commercial stereolithography 3D printing. The incorporation of disulfide bonds within the polymer network's backbone imparts the 3D printed objects with self-healing capabilities and complete degradability. Remarkably, the degraded resin can be fully recycled and reused for high-resolution reprinting of complex structures while preserving mechanical properties that are comparable to the original material. This proof-of-concept study not only presents a sustainable strategy for advancing acrylate-based 3D printing materials, but also introduces a novel approach for fabricating fully recyclable 3D-printed structures. This method paves the way for reducing the environmental impact while enhancing material reusability, offering significant potential for the development of eco-friendly additive manufacturing.

Purchased from AmBeed: ; ;

Zhao, Baoming ; Hao, Cheng ; Chang, Yu-Chung ; Cao, Yiding ; Liu, Tuan ; Fei, Mingen , et al.

Abstract: Carbon fiber-reinforced hollow composites play a vital role in light weighting modern cars and aircrafts. Fabrication of such hollow composites with seamless internal finish requires sacrificial tooling that can be used under pressure and high temperature For the very first time, high performance sacrificial tooling that can be used to fabricate fiber-reinforced hollow composites is produced using photocuring 3D printing technol. This is achieved by developing UV-curable resins containing highly soluble yet hydrolyzable acetal acrylate crosslinker and hydrophilic 4-acryloylmorpholine monomer. It is found that the cross-linker content greatly affects the printing speed. Further, the widely adopted UV post-curing method is found to have negligible impact on improving the thermal-mech. properties of printed structures. After thermal post-treatment, printed sacrificial tooling exhibits a heat deflection temperature of 112°C at 0.455 MPa and an average coefficient of linear thermal expansion of 59 ppm °C-1 between 30 and 100°C. As a result, printed tooling enables fabrication of carbon fiber-reinforced hollow composites with complex geometry, which shows a tensile strength of 802 MPa and an elastic modulus of 50.2 GPa.

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Shao, Lin ; Chang, Yu-Chung ; Zhao, Baoming ; Yan, Xinyan ; Bliss, Brian J. ; Fei, Ming-en , et al.

Abstract: Waste epoxy materials become an enormous problem to society and the environment. The advantages of epoxy resins derive from their rigid and chem. stable networks, but these qualities also make them difficult to dispose of or recycle. Herein, we demonstrated an efficient degradation of anhydride cured epoxy resin by aminolysis in aminoethanol without using any catalysts. The epoxy resin was fully decomposed at 160°C in 4 h, resulting in two distinct high purity monomers (HHPA-OH and BPA-OH). To fully realize this upcycling approach, The BPA-OH was used to synthesize a polyurethane coating with an excellent glass transition temperature (88.9°C), scratch hardness (8H), gouge hardness (6H), adhesive strength (5B), and strong solvent resistance. The HHPA-OH with two hydroxyl groups was reacted with methacrylic anhydride to form a dimethacrylate monomer which was then used as a viable crosslinker for photo-curable 3D printing thermosetting polymer with tensile strength as high as 64 MPa and impact strength of 4.86 kJ/m2. This work demonstrates a feasible pathway to convert anhydride cured epoxy waste to new monomeric recyclates for superior polymer products.

Keywords: Thermosets ; Aminolysis ; Chemical recycling to monomers ; Upcycling ; 3D printing

Purchased from AmBeed:

Lin Shao ; Yu-Chung Chang ; Cheng Hao ; Ming-en Fei ; Baoming Zhao ; Brian J. Bliss , et al.

Abstract: As the demand for PLA increases, post-consumer disposal strategies must be carefully considered. While we would love to embrace a bioplastic future, we also need to tread carefully. Though PLA is widely claimed to be biodegradable, full degradation often requires conditions not typically found in landfills or industrial composting. Therefore, it will negatively impact the environment if treated carelessly. In this work, we report a simple PLA upcycling path to turn existing PLA wastes into new 3D printable materials within 48 hours. The ester bonds of PLA can be cleaved efficiently via aminolysis. The obtained monomeric compound was derivatized with methacrylic anhydride, which introduces double bonds and thus a cross-linkable monomer is obtained. In combination with a comonomer and initiator, a photocurable resin is produced. The resin can be fed into any commercially available photocuring 3D printer. The 3D printed parts derived from PLA wastes exhibit impressive performances with a tensile strength of 58.6 MPa, Young's modulus of 2.8 GPa, and glass transition at ∼180 °C. Our work demonstrates a new route to active upcycling of PLA while minimizing the need for disposal.

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Alternative Products

Product Details of [ 162881-26-7 ]

CAS No. :162881-26-7
Formula : C26H27O3P
M.W : 418.46
SMILES Code : O=C(P(C(C1=C(C)C=C(C)C=C1C)=O)(C2=CC=CC=C2)=O)C3=C(C)C=C(C)C=C3C
MDL No. :MFCD01863675
InChI Key :GUCYFKSBFREPBC-UHFFFAOYSA-N
Pubchem ID :164512

Safety of [ 162881-26-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H317-H413
Precautionary Statements:P261-P272-P273-P280-P302+P352-P333+P313-P362+P364-P501

Computational Chemistry of [ 162881-26-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 30
Num. arom. heavy atoms 18
Fraction Csp3 0.23
Num. rotatable bonds 5
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 125.02
TPSA ?

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

61.02 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

3.88
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

6.0
Log Po/w (WLOGP)?

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

6.21
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.

3.81
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

7.09
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

5.4

Water Solubility

Log S (ESOL):?

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

-6.33
Solubility 0.000196 mg/ml ; 0.000000469 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.

-7.06
Solubility 0.0000365 mg/ml ; 0.0000000873 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

-9.57
Solubility 0.000000111 mg/ml ; 0.0000000003 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

Yes
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

Yes
Log Kp (skin permeation)?

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

-4.59 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

0.0
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

1.0
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)

4.41
 

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