Preparation of Isophorone Diisocyanate Terminated Star Polyethers

Götz, Hans; Beginn, Uwe; Bartelink, Camiel F.; Grünbauer, H. J. M.; Möller, Martin

doi:10.1002/1439-2054(20020401)287:4<223::aid-mame223>3.0.co;2-z

Cited by 54 publications

(24 citation statements)

References 12 publications

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“…surprisingly, this spectrum appears very simple since only three signals, between 121.7 and 122.8 associated with the isocyanate functions, were observed (residual IPDI and terminal groups). [48] Three other well-defined peaks corresponding to the various urethane groups appear clearly at 155.4, 156.4, and 156.6 ppm. [49,50] Therefore, only two unassigned peaks remain at 134.9 and 116.7 ppm, but they cannot be associated with allophanate or biuret (expected around 155 ppm) nor isocyanurate (expected between 150 and 153 ppm) [51,52] or between 157 and 159 ppm.…”

Section: Resultsmentioning

confidence: 99%

Novel nucleophilic/basic and acidic organocatalysts for reaction between poorly reactive diisocyanate and diols

Belmokaddem

Dagonneau

Lhomme

et al. 2016

Designed Monomers and Polymers

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International audienceOriginal basic or acidic organic compounds derived from guanidine or phenyl phosphonic acid were specifically designed and tested as new catalysts for the bulk synthesis of polyurethane prepolymers from a precursor system with particularly low reactivity (secondary alcohol + aliphatic isocyanate at low temperature). Both families showed interesting catalytic activities at 60-80 degrees C, but must nevertheless be used in much higher amounts (1mol%, i.e. between 0.15 and 0.50wt%) than traditional metal-based catalysts. The efficiency of guanidine derivatives seems to be related to their nucleophilicity, whereas that of phosphonic acid derivatives depends on their acidity. However, the solubility of the considered species in the reactive medium also plays a major role. The water/alcohol selectivity of the catalysts, especially at room temperature, was then examined as an additional criterion. Guanidines are not selective and favor the reaction of isocyanate groups with water as much as that with alcohols. Phenyl phosphonic acid derivatives are more selective, and particularly pentafluorophenyl phosphonic acid displays a remarkable catalytic activity together with an acceptable selectivity and could represent an interesting and safer alternative to toxic tin and mercury derivatives for many industrial polyurethanes

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Section: Resultsmentioning

confidence: 99%

Novel nucleophilic/basic and acidic organocatalysts for reaction between poorly reactive diisocyanate and diols

Belmokaddem

Dagonneau

Lhomme

et al. 2016

Designed Monomers and Polymers

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“…[24][25][26][27][28]30] 2-N-acetylamino-2-deoxy-b-D-glucopyranosylazide (b-DGlcNAc-N 3 ) and tert-butyl-N-(3-aminopropyl)-carbamate were prepared according supporting information. TMP from Acros Organics, ethyl chloroformate from Fluka, sodium ascorbate and copper sulfate pentahydrate from Applichem, triethylamine (TEA, 99.5%) from Sigma-Aldrich, propagyl bromide solution (80% in toluene) from Acros Organics, phosphomolybdic acid hydrate from Merck, tetrahydrofuran (THF, p.a.)…”

Section: Methodsmentioning

confidence: 99%

“…[24][25][26][27][28]30] Briefly, these polymers were prepared from star shaped 6-armed statistical copolymers of ethylene oxide/propylene oxide (EO/PO) with a ratio of repeating units of 4:1, prepared via anionic polymerization of the monomer mixture using potassium sorbitol as an initiator. Each arm has a molar mass of 2 kDa and the polydispersity of the star molecule is small (PDI < 1.2).…”

Section: Immobilization and Ella Test Of B-d-glcnac-functionalized Comentioning

confidence: 98%

Synthesis of a Difunctional Orthogonal Coupler for the Preparation of Carbohydrate‐Functionalized sP(EO‐stat‐PO) Hydrogels

Anders

Adamiak

Keul

et al. 2011

Macromolecular Bioscience

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The synthesis and characterization of a new difunctional coupler (4) based on trimethylolpropane (TMP) are described. The coupler is used to connect biologically active N-acetylglucosamine (GlcNAc) on amino-reactive microtiter plates and on star-shaped poly[(ethylene oxide)-stat-(propylene oxide)] hydrogel layers in microtiter plates. The biological activity of immobilized carbohydrates is determined using an enzyme-linked lectin assay.

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“…Substrates were activated by O 2 -plasma treatment for 15 min (400 W, 50 sccm, and 0.4 mbar) and aminosilanized with 3-aminopropyl-trimethoxysilan at 5 mbar. NCO-sP(EO-stat-PO) prepolymers were synthesized as described elsewhere 27 and solubilized in tetrahydrofuran (THF) under inert gas atmosphere. Water was added to the NCO-sP(EO-stat-PO) solution (THF/H 2 O 1/9) to yield a final prepolymer concentration of 10 mg/ml.…”

Section: A Hydrogel Coatingmentioning

confidence: 99%

Quantifying ligand–cell interactions and determination of the surface concentrations of ligands on hydrogel films: The measurement challenge

et al. 2015

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Hydrogels are extensively studied for biomaterials application as they provide water swollen noninteracting matrices in which specific binding motifs and enzyme-sensitive degradation sites can be incorporated to tailor cell adhesion, proliferation, and migration. Hydrogels also serve as excellent basis for surface modification of biomaterials where interfacial characteristics are decisive for implant success or failure. However, the three-dimensional nature of hydrogels makes it hard to distinguish between the bioactive ligand density at the hydrogel-cell interface that is able to interact with cells and the ligands that are immobilized inside the hydrogel and not accessible for cells. Here, the authors compare x-ray photoelectron spectrometry (XPS), time-of-flight secondary ion mass spectroscopy (ToF-SIMS), enzyme linked immunosorbent assay (ELISA), and the correlation with quantitative cell adhesion using primary human dermal fibroblasts (HDF) to gain insight into ligand distribution. The authors show that although XPS provides the most useful quantitative analysis, it lacks the sensitivity to measure biologically meaningful concentrations of ligands. However, ToF-SIMS is able to access this range provided that there are clearly distinguishable secondary ions and a calibration method is found. Detection by ELISA appears to be sensitive to the ligand density on the surface that is necessary to mediate cell adhesion, but the upper limit of detection coincides closely with the minimal ligand spacing required to support cell proliferation. Radioactive measurements and ELISAs were performed on amine reactive well plates as true 2D surfaces to estimate the ligand density necessary to allow cell adhesion onto hydrogel films. Optimal ligand spacing for HDF adhesion and proliferation on ultrathin hydrogel films was determined as 6.5 ± 1.5 nm.

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Preparation of Isophorone Diisocyanate Terminated Star Polyethers

Cited by 54 publications

References 12 publications

Novel nucleophilic/basic and acidic organocatalysts for reaction between poorly reactive diisocyanate and diols

Novel nucleophilic/basic and acidic organocatalysts for reaction between poorly reactive diisocyanate and diols

Synthesis of a Difunctional Orthogonal Coupler for the Preparation of Carbohydrate‐Functionalized sP(EO‐stat‐PO) Hydrogels

Quantifying ligand–cell interactions and determination of the surface concentrations of ligands on hydrogel films: The measurement challenge

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