Ethylene glycol dimethacrylate: Difference between revisions

Browse history interactively

← Previous edit

Content deleted Content added

VisualWikitext

@@ Line 1: / Line 1: @@
 {{Chembox
+| Watchedfields = changed
-| verifiedrevid = 443745011
+| verifiedrevid = 443747062
-| Reference = <ref>[http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=335681|ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC Ethylene glycol dimethacrylate] at [[Sigma-Aldrich]]</ref>
+| Reference = <ref>{{cite web | url = http://www.sigmaaldrich.com/US/en/product/aldrich/335681 | title = Ethylene glycol dimethacrylate | publisher = [[Sigma-Aldrich]] }}</ref>
-| ImageFile = Ethylene glycol dimethacrylate.png
+| ImageFile = Ethylene glycol dimethylacrylate Structural Formula V1.svg
 | ImageSize = 220px
 | ImageName = Skeletal formula
@@ Line 8: / Line 9: @@
 | ImageSize1 = 240px
 | ImageName1 = Ball-and-stick model
+| PIN = Ethane-1,2-diyl bis(2-methylprop-2-enoate)
-| IUPACName =  2-(2-Methyl-acryloyloxy)ethyl 2-methyl-acrylate
-| OtherNames = Methacrylic acid, ethylene ester; 1,2-Bis(methacryloyloxy)ethane; 1,2-Ethanediol dimethacrylate; Diglycol dimethacrylate; Ethanediol dimethacrylate; Ethylene dimethacrylate; Ethylene glycol bis(methacrylate); Ethylene glycol dimethacrylate; Ethylene methacrylate
+| OtherNames = Methacrylic acid, ethylene ester; 1,2-Bis(methacryloyloxy)ethane; 1,2-Ethanediol dimethacrylate; Diglycol dimethacrylate; Ethanediol dimethacrylate; Ethylene dimethacrylate; Ethylene glycol bis(methacrylate); Ethylene glycol dimethacrylate; Ethylene methacrylate; 2-(Methacryloyloxy)ethyl methacrylate
-| Section1 = {{Chembox Identifiers
+|Section1={{Chembox Identifiers
 | Abbreviations = EGDMA
 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
@@ Line 16: / Line 17: @@
 | UNII_Ref = {{fdacite|correct|FDA}}
 | UNII = 7BK5G69305
-| InChI = 1/C10H14O4/c1-7(2)9(11)13-5-6-14-10(12)8(3)4/h1,3,5-6H2,2,4H3
-| InChIKey = STVZJERGLQHEKB-UHFFFAOYAH
 | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChI = 1S/C10H14O4/c1-7(2)9(11)13-5-6-14-10(12)8(3)4/h1,3,5-6H2,2,4H3
@@ Line 24: / Line 23: @@
 | CASNo_Ref = {{cascite|correct|CAS}}
 | CASNo = 97-90-5
-| PubChem =
+| PubChem = 7355
 | ChEBI_Ref = {{ebicite|correct|EBI}}
 | ChEBI = 53436
+| ChEMBL = 1709582
+| Beilstein = 1776663
+| Gmelin = 637376
+| EC_number = 202-617-2
+| RTECS = OZ4400000
 | SMILES = CC(=C)C(=O)OCCOC(=O)C(=C)C
 }}
-| Section2 = {{Chembox Properties
+|Section2={{Chembox Properties
 | C=10 | H=14 | O=4
 | Appearance =
 | Density = 1.051 g/mL
+| MeltingPtC = −40
-| MeltingPt =
-| BoilingPt = 98-100 °C (5 mmHg)
+| BoilingPtC = 98 to 100
+| BoilingPt_notes = (5 mmHg)
 | Solubility = }}
-| Section3 = {{Chembox Hazards
+|Section3={{Chembox Hazards
 | MainHazards =
-| FlashPt =
+| FlashPtC = 101
-| Autoignition = }}
+| AutoignitionPt =
+| GHSPictograms = {{GHS07}}
+| GHSSignalWord = Warning
+| HPhrases = {{H-phrases|315|317|319|335|412}}
+| PPhrases = {{P-phrases|261|264|271|272|273|280|302+352|304+340|305+351+338|312|321|332+313|333+313|337+313|362|363|403+233|405|501}}
+ }}
 }}
-'''Ethylene glycol dimethylacrylate''' (EGDMA) is a [[ester|diester]] formed by [[condensation]] of two equivalents of [[methacrylic acid]] and one equivalent of [[ethylene glycol]].<ref>Bielstein 2, IV, 1532</ref>
+'''Ethylene glycol dimethylacrylate''' ('''EGDMA''') is a [[ester|diester]] formed by [[condensation]] of two equivalents of [[methacrylic acid]] and one equivalent of [[ethylene glycol]].<ref>Bielstein 2, IV, 1532</ref>
-EGDMA can be used in [[free radical]] [[copolymer]] [[crosslinking]] reactions.  When used with [[methyl methacrylate]], it leads to [[gel point]] at relatively low [[concentration]]s because of the nearly equivalent reactivities of all the [[double bonds]] involved.
+EGDMA can be used in [[free radical]] [[copolymer]] [[Cross-link|crosslinking]] reactions.  When used with [[methyl methacrylate]], it leads to [[gel point]] at relatively low [[concentration]]s because of the nearly equivalent reactivities of all the [[double bond]]s involved.
+It is used as a monomer to prepare hydroxyapatite/poly methyl methacrylate composites. EGDMA can be used in free radical copolymer crosslinking reactions.
+Its toxicity profile has been fairly well studied.<ref>{{Cite journal |last1=Bielecka-Kowalska |first1=Anna |last2=Czarny |first2=Piotr |last3=Wigner |first3=Paulina |last4=Synowiec |first4=Ewelina |last5=Kowalski |first5=Bartosz |last6=Szwed |first6=Marzena |last7=Krupa |first7=Renata |last8=Toma |first8=Monika |last9=Drzewiecka |first9=Malgorzata |last10=Majsterek |first10=Ireneusz |last11=Szemraj |first11=Janusz |last12=Sliwinski |first12=Tomasz |last13=Kowalski |first13=Michał |date=March 2018 |title=Ethylene glycol dimethacrylate and diethylene glycol dimethacrylate exhibits cytotoxic and genotoxic effect on human gingival fibroblasts via induction of reactive oxygen species |url=https://linkinghub.elsevier.com/retrieve/pii/S0887233317303363 |journal=Toxicology in Vitro |language=en |volume=47 |pages=8–17 |doi=10.1016/j.tiv.2017.10.028}}</ref> It is sometimes called '''ethylene dimethacrylate'''.<ref>{{Cite web |last=PubChem |title=Ethylene glycol dimethacrylate |url=https://pubchem.ncbi.nlm.nih.gov/compound/7355 |access-date=2023-03-16 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
 ==References==
 {{reflist}}
-[[Category:Carboxylate esters]]
+[[Category:Monomers]]
+[[Category:Methacrylate esters]]
+[[Category:Glycol esters]]
+{{alkene-stub}}
 {{ester-stub}}