2,2'-[(1-Methylethyliden)bis(4,1-phenylenoxymethylen)]bisoxiran

Bezeichnung:2,2'-[(1-Methylethyliden)bis(4,1-phenylenoxymethylen)]bisoxiran

CAS-Nr1675-54-3

Englisch Name:BISPHENOL A DIGLYCIDYL ETHER RESIN

CBNumberCB3749115

SummenformelC21H24O4

Molgewicht340.41

MOL-Datei1675-54-3.mol

Synonyma

2,2'-[(1-Methylethyliden)bis(4,1-phenylenoxymethylen)]bisoxiran

2,2-bis(4-(2,3-Epoxypropoxy)phenyl)propan

Dimethylmethandiglycidylether

2,2'-[(1-Methylethyliden)bis(4,1-phenylenoxymethylen)]bisoxiran physikalisch-chemischer Eigenschaften

Schmelzpunkt	40-44 °C
Siedepunkt	210 °C / 1mmHg
Dichte	1,17 g/cm³
Dampfdruck	0Pa at 25℃
Brechungsindex	1.5735
storage temp.	Inert atmosphere,2-8°C
Löslichkeit	Soluble in DMSO (up to 30 mg/ml) or in Ethanol (up to 15 mg/ml)
Aggregatzustand	viscous liquid
Farbe	White
Wasserlöslichkeit	Soluble in 100% ethanol, dimethyl sulfoxide (100 mM), dimethyl formamide, chloroform, methanol, and ethanol (50 mM). Insoluble in water.
BRN	299026
Stabilität	Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
LogP	3.242 at 25℃
CAS Datenbank	1675-54-3(CAS DataBase Reference)
IARC	3 (Vol. 47, 71) 1999
EPA chemische Informationen	Bisphenol A diglycidyl ether (1675-54-3)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/38-43
S-Sätze:	28-37/39
WGK Germany	1
RTECS-Nr.	TX3800000
TSCA	Yes
HS Code	2910900090
Giftige Stoffe Daten	1675-54-3(Hazardous Substances Data)
Toxizität	LD50 oral in rabbit: 1980mg/kg

Gefahreninformationscode (GHS)

BISPHENOL A DIGLYCIDYL ETHER RESIN Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD
GERUCHLOSE, GELBLICHBRAUNE, VISKOSE FLüSSIGKEIT.
CHEMISCHE GEFAHREN
Bildung explosionsfähiger Peroxide wahrscheinlich. Reagiert mit starken Oxidationsmitteln.
ARBEITSPLATZGRENZWERTE
TLV nicht festgelegt (ACGIH 2005).
MAK: Hautresorption; Sensibilisierung der Haut; Krebserzeugend Kategorie 3A; (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation der Dämpfe.
INHALATIONSGEFAHREN
Nur ungenügende Angaben vorhanden über die Geschwindigkeit, mit der eine gesundheitsschädliche Konzentration in der Luft beim Verdampfen bei 20°C erreicht wird.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION:
Die Substanz reizt die Augen und die Haut. Exposition könnte Bewusstseinstrübung verursachen.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Wiederholter oder andauernder Hautkontakt kann zu Dermatitis und Hautsensibilisierung führen.
LECKAGE
Belüftung. Ausgelaufene Flüssigkeit möglichst in abdichtbaren Behältern sammeln. Reste mit viel Wasser wegspülen. Persönliche Schutzausrüstung: Atemschutzfilter für organische Gase und Dämpfe.
R-Sätze Betriebsanweisung:
R36/38:Reizt die Augen und die Haut.
R43:Sensibilisierung durch Hautkontakt möglich.
S-Sätze Betriebsanweisung:
S28:Bei Berührung mit der Haut sofort abwaschen mit viel . . . (vom Hersteller anzugeben).
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Beschreibung
Most epoxy resins result from polymerization of bisphenol A diglycidyl ether (BADGE). Delayed hypersensitivity is caused by the low-molecular-weight monomer BADGE (MW 340 g/mol), the dimer having a much lower sensitization power. This allergen caused contact dermatitis in six workers in a plant producing printed circuits boards made of copper sheets and fiberglass fabric impregnated with a brominated epoxy resin. It can also be contained in adhesives.
Beschreibung
PPARγ is a ligand-activated transcription factor involved in the regulation of lipid homeostasis and may function as a master regulator of adipogenesis. Ligands for PPARγ include antidiabetic drugs of the thiazolidinedione structural class, 15-deoxy-Δ^12,14-prostaglandin J₂ , and NSAIDS. BADGE is a synthetic compound used in the production of polycarbonate and industrial plastics. This compound was recently identified as an antagonist of PPARγ. BADGE binds to PPARγ with an apparent K_d of 100 μM and interferes with the ability of 3T3-L1 and 3T3-F442A cells to undergo hormone-mediated cell differentiation.
Chemische Eigenschaften
Diglycidyl ether of bisphenol A is a colorless to light amber liquid. Slight epoxy odor.
Verwenden
Bisphenol A derivative. A PPARγ antagonist; exhibits estrogenic activity; An inhibitor of PPARγ and suppressor of TNFα.
Verwenden
The uniqueness of D.E.R. 332 epoxy resin is reflected in its maximum epoxide equivalent weight of 178. Because of its high purity and lack of polymer factions, samples embedded using D.E.R. 322 have uniform performance, exceptionally low viscosity and color; and improved elevated temperature properties.
Verwenden
In the manufacture of epoxy resins and polycarbonates for food packaging.
Definition
ChEBI: Bisphenol A diglycidyl ether is a diarylmethane.
Vorbereitung Methode
The synthesis of the basic epoxy resin molecule involves the reaction of epichlorohydrin with bisphenol A, the latter requiring two basic intermediates for synthesis, acetone and phenol. Theoretically, the production of the bisphenol A diglycidyl ether requires 2 mol of epichlorohydrin for each mole of the phenol. Epoxy resins of higher molecular weight are obtained by reducing the epichlorohydrin/bisphenol A ratio. This reaction involves consumption of the initial epoxy groups in the epichlorohydrin and of some of the groups formed by dehydrohalogenation.
Allgemeine Beschreibung
Odorless yellowish brown liquid. Sinks in water.
Air & Water Reaktionen
Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick 1979 p.151-154, 164]. Insoluble in water.
Reaktivität anzeigen
Epoxides, such as BISPHENOL A DIGLYCIDYL ETHER RESIN, are highly reactive. They polymerize in the presence of catalysts or when heated. These polymerization reactions can be violent. Compounds in this group react with acids, bases, and oxidizing and reducing agents. They react, possibly violently with water in the presence of acid and other catalysts.
Health Hazard
Contact with liquid irritates eyes. Prolonged or repeated contact with skin causes irritation and dermatitis.
Brandgefahr
BISPHENOL A DIGLYCIDYL ETHER RESIN is probably combustible.
Biologische Aktivität
PPAR γ pure antagonist with micromolar affinity in 3T3-L1 and 3T3-F442A preadipocyte cells; selective over PPAR δ and PPAR α . Antagonizes the ability of rosiglitazone to stimulate transcriptional activity of PPAR γ . Acts as a PPAR γ agonist in an ECV304 cell line. Also produces PPARg-independent apoptosis of tumor cells via several mechanisms. Active in vivo .
Kontakt-Allergie
Most epoxy resins result from polymerization of bisphenol A diglycidyl ether (BADGE). Delayed hypersensitivity is caused by the low-molecular-weight monomer BADGE (Molecular Weight 340 g/mol), the dimer having much a lower sensitization power. This allergen caused contact dermatitis in six workers in a plant producing printed circuits boards made of copper sheets and fiber glass fabric impregnated with a brominated epoxy resin. It can be contained in adhesives.
Biochem/physiol Actions
PPARγ inhibitor that blocks rosiglitazone- and insulin-induced adipogenesis.
mögliche Exposition
Diglycidyl ether of bisphenol A is used as a basic active ingredient of epoxy resins.
Erste Hilfe
If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.
Carcinogenicity
In summary, a number of carcinogenicity studies involving the topical application of pure BADGE as well as EPON Resin 828 and other commercial BADGE-based resins have been carried out in experimental animals.Viewing the studies as a whole, the weight of evidence does not show that BADGE or BADGE-based epoxy resins are carcinogenic.
Lager
Color Code—Blue: Health Hazard (skin sensitization): Store in a secure location. Prior to working with thischemical you should be trained on its proper handling andstorage. Store in tightly closed containers in a dark, cool,well-ventilated area away from strong oxidizers, acids, and heat. Recommended storage (and pumping)temperature=45-50℃.
Versand/Shipping
This material is not covered in DOT’sPerformance-Oriented Packaging Standards. It may,however, be classified as a Combustible Liquid, n.o.s. Thisclass requires no shipping label. It falls in Hazard Class 3[each reference to a Class 3 material is modified to read“COMBUSTIBLE LIQUID” when that material is reclassified in accordance with y173.150 (e) or (f) of this subchapter or has a flash point above 60.5℃/141°F but below93℃/200°F], and Packing Group III. The symbol “D” identifies proper shipping names which are appropriate fordescribing materials for domestic transportation but may beinappropriate for international transportation under the provisions of international regulations (e.g., IMO, ICAO). Analternate proper shipping name may be selected when eitherdomestic or international transportation is involved.
Inkompatibilitäten
Easily oxidized in air; presumed to form unstable and explosive peroxides in storage. Incompatible with strong acids; strong oxidizers.
Waste disposal
Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Einzelnachweise
1) Cuzzocrea?et al. (2004),?Rosiglitazone , a ligand of the peroxisome proliferator-activated receptor-gamma, reduces acute inflammation; Eur. J. Pharmacol.,?483?79 2) Fehlberg?et al. (2003),?Bisphenol A diglycidyl ether-induced apoptosis involves Bax/Bid-dependent mitochondrial release of apoptosis-inducing factor (AIF), cytochrome c and Smac/DIABLO; Br. J. Pharmacol.,?139?495 3) Chamorro-Garcia?et al.?(2012),?Bisphenol A diglycidyl ether induces adipogenic differentiation of multipotent stromal stem cells through a peroxisome proliferator-activated receptor gamma-independent mechanism; Environ. Health Perspect.,?120?984 4) Duque?et al. (2013),?Pharmacological inhibition of PPARgamma increases osteoblastogenesis and bone mass in male C57BL/6 mice; J. Bone Miner. Res.,?28?639

BISPHENOL A DIGLYCIDYL ETHER RESIN Upstream-Materialien And Downstream Produkte

2,2'-[(1-Methylethyliden)bis(4,1-phenylenoxymethylen)]bisoxiran Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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