Comparison of life-stage-dependent internal dosimetry for bisphenol a, ethinyl estradiol, a reference estrogen, and endogenous estradiol to test an estrogenic mode of action in Sprague Dawley rats. The hydroxy group may be derived from aliphatic diols, polyols (polyether polyols), phenolic compounds or dicarboxylic acids. The synthesis of diglycidyl ether of bisphenol A (DGEBA), the most widely used epoxy resin monomer, is: FDA will update its assessment of BPA and will take additional action if warranted. The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely. Developed physiologically based pharmacokinetic models that can be used to predict the level of internal exposure to the active and inactive forms of BPA. It belongs to the phenol class of aromatic organic compounds. Chemical Identity. Structural formula Name CAS Reactants; Bisphenol AF: 1478-61-1: Phenol: Hexafluoroacetone: Bisphenol F: 620-92-8: Phenol: It can also be used in the formation of solid polymeric electrolyte for potential application in electrochemical devices. One reason people may be concerned about BPA is because human exposure to BPA is widespread. The study orally dosed pregnant rodents with 100-1000 times more BPA than people are exposed to through food, and could not detect the active form of BPA in the fetus 8 hours after the mother's exposure. In addition to the FDA review process, FDAs Acting Chief Scientist asked five expert scientists from across the federal government to provide independent scientific review of these documents in the fall of 2009. [7] Thus, in bisphenol F, the F signifies formaldehyde. FDA can take this action on its own initiative or in response to a food additive petition that demonstrates that a use of a food additive has been permanently and completely abandoned. The lowest molecular weight an epoxy resin of the DGEBA type can have is 340, but if two elements together can form different molecular weights when they react, the epoxy resin will contain a mixture of epoxy molecules of varying lengths. Bottle producers have largely switched from polycarbonate to polypropylene and there is some evidence that BPA exposure in infants has decreased as a result of this. This process, also known as a one-step process, is commonly used for the preparation of low and medium molecular weight bisphenol A epoxy resins. The ACC mark, Responsible Care, the hands logo mark, CHEMTREC, TRANSCAER, and americanchemistry.com are registered service marks of the American Chemistry Council, Inc. May also be known as: Polycarbonate, Epoxy Resins. [21] BPA has been investigated by public health agencies in many countries, as well as by the World Health Organization. .mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}, Bisphenol A (BPA) is a chemical compound primarily used in the manufacturing of various plastics. General description. [74] It binds to both of the nuclear estrogen receptors (ERs), ER and ER. To improve the compatibility between flame retardant and epoxy resin (EP) matrix, amino phenyl copper phosphate-9, 10-dihydro-9-oxygen-10-phospha-phenanthrene-10-oxide (CuPPA-DOPO) is synthesized through surface grafting, which is blended with EP matrix to prepare EP/CuPPA-DOPO composites. As a result, FDA amended its food additive regulations to no longer provide for these uses of BPA. The FDA review has not found any information in the evaluated studies to prompt a revision of FDAs safety assessment of BPA in food packaging at this time. In fact, the Federal Trade Commission has specifically cautioned that free-of claims may deceive consumers by falsely suggesting that the marketer has improved the product by removing the substance.. read more. Questions & Answers on Bisphenol A Use in Food Contact Applications, Bisphenol A Overview & Response to Petitions, European Food Safety Authority Information on Bisphenol A. The ACC petition demonstrated, from publicly available information and information collected from industry sources, that the use of polycarbonate resins in baby bottles and sippy cups had been abandoned. BPA is fairly cheap to produce, as the synthesis benefits from a high atom economy and large amounts of both starting materials are available from the cumene process. [70][71] The body first converts it into more water-soluble compounds via glucuronidation or sulfation, which are then removed from the body through the urine. The molecular structure of bisphenol A epoxy resin contains aromatic rings and lateral hydroxyl groups, which is beneficial to improve adhesion; in addition, the aromatic ring structure also gives the resin higher rigidity, tensile strength and thermal stability; in general, The main characteristics of bisphenol A epoxy type include: fast light curing reaction rate, high hardness and tensile strength after curing, high gloss of the film layer, and excellent chemical corrosion resistance. The method is a modification of NIOSH P&CAM This early work underpinned the development of epoxy resins, which in turn motivated production of BPA. Some are conducted according to internationally recognized standards that ensure methodological and statistical reliability, and others are not. Bisphenol A- (epichlorhydrin)epoxy resin, polymer with polyethylene glycol, castor oil and triethylenetetramine IUPAC names 1 Print infocard Substance identity Substance identity The 'Substance identity' section is calculated from substance identification information from all ECHA databases. Epoxy is the family of basic components or cured end products of epoxy resins.Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. Bisphenol A | C15H16O2 | CID 6623 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. [98] Despite its short half-life and non-bioaccumulating character, the continuous release of BPA into the environment causes continuous exposure to both plant[104] and animal life. The performance represented by each part of the Bisphenol A-type epoxy resin is shown here: Araldite? NIEHS provides many opportunities for funding to individual researchers, organizations, and businesses. to be exposed to dangerous levels of bisphenol A epoxy diacrylate. Because of its extreme durability and strength, polycarbonate plastic is particularly useful for making component parts that need to be thin and light, but strong. [99] Regardless, the remaining 29% of BPA will continue through to the environment, with low levels of BPA commonly observed in surface water and sediment in the U.S. and Europe. There is some evidence that BPA exposure in infants has decreased as a result of this. Polycarbonate plastic also is used to make housings for electronic products such as cell phones and laptops, as well as optical discs such as CDs and DVDs. This orphan receptor (endogenous ligand unknown) behaves as a constitutive activator of transcription. Epoxy vinyl ester resins (VER), Often shortened to vinyl esters, are an important class of high-performance thermoset molding resins. . Regardless, due to the scientific uncertainty, many jurisdictions have taken steps to reduce exposure on a precautionary basis. Compounds without a Phenanthrene Nucleus", "Bio-Based Aromatic Epoxy Monomers for Thermoset Materials", "European Union Summary Risk Assessment Report - Bis (2-ethylhexyl) Phthalate (DEHP)", "Bisphenol S and F: A Systematic Review and Comparison of the Hormonal Activity of Bisphenol A Substitutes", "Exposure of the U.S. population to bisphenol A and 4-tertiary-octylphenol: 2003-2004", "The state of bisphenol research in the lesser developed countries of the EU: a mini-review", "An extensive new literature concerning low-dose effects of bisphenol A shows the need for a new risk assessment", "Bisphenol A and baby bottles: challenges and perspectives", "Consolidated federal laws of canada, Canada Consumer Product Safety Act", "MSC unanimously agrees that Bisphenol A is an endocrine disruptor - All news - ECHA", "EU court confirms BPA as substance of 'very high concern', "Estrogen biology: new insights into GPER function and clinical opportunities", "Global Assessment of Bisphenol A in the Environment: Review and Analysis of Its Occurrence and Bioaccumulation", "A critical analysis of the biological impacts of plasticizers on wildlife", Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione), DHEA (androstenolone, prasterone; 5-DHEA), 7-Methyl-19-norandrostenedione (MENT dione, trestione), 11-Methyl-19-nortestosterone dodecylcarbonate, Normethandrone (methylestrenolone, normethisterone), Oxabolone cipionate (oxabolone cypionate), Methylclostebol (chloromethyltestosterone), Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4), Enobosarm (ostarine, MK-2866, GTx-024, S-22), 3-Methyl-19-methyleneandrosta-3,5-dien-17-ol, 10,17-Dihydroxyestra-1,4-dien-3-one (DHED), 16,17-Epiestriol (16-hydroxy-17-estradiol), 17-Epiestriol (16-hydroxy-17-estradiol), Epiestriol (16-epiestriol, 16-hydroxy-17-estradiol), Fosfestrol (diethylstilbestrol diphosphate), Furostilbestrol (diethylstilbestrol difuroate), Triphenylmethylethylene (triphenylpropene), https://en.wikipedia.org/w/index.php?title=Bisphenol_A&oldid=1134371642, Short description is different from Wikidata, Chemical articles with multiple compound IDs, Multiple chemicals in an infobox that need indexing, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Creative Commons Attribution-ShareAlike License 3.0, Polycyanurates can be produced from BPA by way of its di-, Bisphenol-A formaldehyde resins are a subset of, BPA is used as an antioxidant in several fields, particularly in, Several drug candidates have also been developed from bisphenol A, including, Reprinted in condensed form in: A. Dianin (1892), This page was last edited on 18 January 2023, at 10:18. [9][10] The manufacturing of epoxy resins and vinyl ester resins account for 2530% of BPA use. Bisphenol A Epoxy Resin (CAS No. Bisphenol A was investigated in the 1930s during the search for synthetic estrogens. FDA has amended its regulations to no longer provide for the use of BPA-based polycarbonate resins in baby bottles and sippy cups. Cured epoxy resins are inert materials used as protective liners in metal cans to maintain the quality of canned foods and beverages, and have achieved wide acceptance for use as protective coatings because of their exceptional combination of toughness, adhesion, formability, and chemical resistance. It is found in various products including shatterproof windows, eyewear, water bottles, and epoxy resins that coat some metal food cans, bottle tops, and water supply pipes. The health effects of BPA have been the subject of prolonged public and scientific debate. BPA is also found in epoxy resins, which act as a protective lining on the inside of some metal-based food and beverage cans. Concerns about the health effects of BPA have led some manufacturers replacing it with other bisphenols, such as bisphenol S and bisphenol F. These are produced in a similar manner to BPA, by replacing acetone with other ketones, which undergo analogous condensation reactions. The 2003-2004 National Health and Nutrition Examination Survey (NHANES III) conducted by the Centers for Disease Control and Prevention (CDC) found detectable levels of BPA in 93% of 2517 urine samples from people six years and older. The chemical formula of Bisphenol A is C15H16O2. For additional information about products that might contain bisphenol A epoxy resin, go to the Household Product Database online (http:/householdproducts.nlm.nih.gov) at the . Epoxy groups located at both ends of the molecule can undergo reactions of ring-opening, cross-linking and solidity with amines, anhydrides, and other curing agents of epoxy resins. The results of the CLARITY Study, a 5+ year, multipronged U.S. federal government research program and the largest study ever done on BPA, confirm BPAs safety. [5] Although the reassessments indicated a need to further evaluate a number of endpoints or biological outcomes, the analyses did not recommend any adjustments to BPA levels reported in food at that time. Polymerisation is achieved by a reaction with phosgene, conducted under biphasic conditions; the hydrochloric acid is scavenged with aqueous base. In the fall of 2014, FDA experts from across the agency, specializing in toxicology, analytical chemistry, endocrinology, epidemiology, and other fields, completed a four-year review of more than 300 scientific studies. Explore thermosetting epoxy resins in detail along with their key properties and understand what makes them an ideal choice in so many applications. BISPHENOL A DIGLYCIDYL ETHER RESIN Chemical Properties,Uses,Production Introduction Bisphenol A diglycidyl ether (DGEBA) is a pale yellow liquid epoxy compound formed by the polycondensation of epichlorohydrin (ECH) and bisphenol A (BPA). Product. Transfer to a pear-shaped separatory funnel to separate the liquid, continue washing and separating with deionized water until the solution turns to neutral from alkaline. . The site is secure. Studies are different, and all are not of the same quality. FDAs regulatory Centers and FDAs National Center for Toxicological Research continue to pursue a set of studies on the fate of BPA in the body from various routes of exposure and the safety of low doses of BPA, including assessing novel endpoints where questions have been raised. Advantage Description. from modified natural oils and Bisphenol A or Bisphenol A-based epoxy resins. BPA is a starting material for the synthesis of plastics, primarily certain polycarbonates and epoxy resins, as well as some polysulfones and . Theres a potential for harm or injury in nearly every activity we engage in whether its when we cross a street, ride in an automobile, or play in a baseball game. Phenols can be compounds such as bisphenol A and novolak. Search for free and find new suppliers for chemical products, pharmaceuticals and APIs. Toxicol Sci. 2010 Dec 15;199(3):372-6. j) Ferguson SA, Law CD Jr, Abshire JS. Polycarbonate drinks containers are also a source of exposure, although most disposable drinks bottles are actually made of PET, which contains no BPA. Order: 200 kg Qingdao Cemo Technology Develop Co., Ltd. The conclusion is not based simply on the number of studies, but more importantly on their quality and scientific value. These chemicals are commonly used to form industrial epoxy resins, plastics, and flame retardants. Developmental treatment with bisphenol A or ethinyl estradiol causes few alterations on early preweaning measures. 40:35-40. The amorphous structure of CuPPA-DOPO is characterized by X-ray diffraction and Fourier-transform . [34] These are not always removed and are known impurities in commercial samples of BPA. An amendment of the food additive regulations based on abandonment is not based on safety, but is based on the fact that the regulatory authorization is no longer necessary for the specific use of the food additive because that use has been permanently and completely abandoned. When possible, opt for glass, porcelain or stainless steel containers, particularly for hot food or liquids. Scientific research shows that in humans, BPA is quicklymetabolized and eliminated from the body it does not accumulate in blood or tissues. Usage/Application: Polycarbonate , Epoxy resin, Thermal paper. In addition to receptor binding, the compound has been found to affect Leydig cell steroidogenesis, including affecting 17-hydroxylase/17,20 lyase and aromatase expression and interfering with LH receptor-ligand binding. Toxicol Lett. It is not a plasticizer,[11] although it is often wrongly labelled as such. PA is also used in the production of epoxy resins. Polycarbonate plastic used in automobiles helps make cars lighter and more fuel-efficient while maintaining safety. The subchronic study was designed to characterize potential effects of BPA in a wide range of endpoints, including prostate and mammary glands, metabolic changes, and cardiovascular endpoints. Usage: Industrial. Chemical Name: Hydrogenated Bisphenol A Epoxy Resin CAS No. [73] Concern is mostly related to its estrogen-like activity, although it can interact with other receptor systems as an endocrine-disrupting chemical. The overall health of the world economy will continue to play a major role in future demand for bisphenol A, as its derivatives' major end-use markets include automotive, construction, and electrical/electronic applications. Copyright 2022 ChemicalBook. Plastic containers have recycle codes on the bottom. This results in much lower internal exposure of BPA (i.e., the active form) than what occurs from other routes of exposure such as injection. [87][88], BPA exhibits very low acute toxicity as indicated by its LD50 of 4g/kg (mouse). People are generally exposed to minute levels of BPA, mostly from the ingestion of food or beverages that have been in contact with materials manufactured with BPA. Use the browser controls to adjust the font size, or print this page. Polycarbonate plastic made with BPA is shatter-resistant, lightweight, and has high optical clarity, similar to glass. BPA is an important industrial chemical, which is mainly used as a raw material of polycarbonate and epoxy resin. Toxicol Lett. Diglycidyl ether of bisphenol A epoxy resin (EPOLAM 2017), and 3-minomethyl-3,5,5 trimethylclohexylamine hardener (EPOLAM 2018). BPA has been used in food packaging since the 1960s. [95] Many of the largest sources of BPA pollution are water-based, particularly wastewater from industrial facilities using BPA. Empirical Formula (Hill Notation): C21H24O4 CAS Number: 1675-54-3 Molecular Weight: 340.41 Beilstein: 299026 EC Number: 216-823-5 MDL number: MFCD00080480 PubChem Substance ID: 57654090 NACRES: NA.77 Pricing and availability is not currently available. BPA is best known for its use in the manufacture of polycarbonate plastics and epoxy resins, particularly those found in water bottles, baby bottles, and other beverage and food containers. At last,Bisphenol A epoxy resin() safety, risk, hazard and . Background. . [65][24], As a result of the presence of BPA in plastics and other commonplace materials, most people are frequently exposed to trace levels of BPA. What chemicals are in epoxy resin when you consider this? [48] BPA is a major component of several high-performance plastics, the production of these is low compared to other plastics but still equals several thousand tons a year. All rights reserved, 2,2-[(1-methylethylidene)bis(4,1-phenyleneoxymethylene)]bis[oxirane],homopoly, 4,4-(1-methylthylidene)bisphenol,polymerwith2,2-[(1-methylethylidene)bis(, Poly(Bisphenol A-co-epichlorohydrin) average Mw ~40,000, pellets, 4-(1-methylethylidene)bisphenol,-polymerwith(chloromethyl)oxirane, bis(4,1-phenyleneoxymethylene)]bis[oxirane], diglycidyletherofbisphenola-basedepoxyresins,lowmolecularweight, lowmolecularweightliquiddgebpa-basedepoxyresins, lowmolecularweightsoliddgebpa-basedepoxyresins, Phenol,4,4-(1-methylethylidene)bis-,polymerwith(chloromethyl)oxirane, phenol,4,4-isopropylidenedi-,dimerwith1-chloro-2,3-epoxypropane, phenol,4,4-isopropylidenedi-,monomerwith1-chloro-2,3-epoxypropane, phenol,4,4-isopropylidenedi-,polymerwith1-chloro-2,3-epoxypropane, phenol,4,4-isopropylidenedi-,tetramerwith1-chloro-2,3-epoxypropane, 2,2-Bis(p-hydroxyphenyl)propane-epichlorohydrin condensate, 2,2-Bis(p-hydroxyphenyl)propane-epichlorohydrin copolymer, 2,2-Bis(p-hydroxyphenyl)propane-epichlorohydrin polymer, 2,2-Diphenylolpropane-epichlorohydrin polymer, 4,4'-ISOPROPYLIDENEDIPHENOL/EPICHLOROHYDRIN COPOLYMER, 4,4-ISOPROPYLIDENEDIPHENOLEPICHLOROHYDRINRESIN, PHENOL44METHYLETHYLIDENEBISPOLYMERWITHCHLOROMETHYLOXIRANE, Reaktionsprodukt aus Bisphenol-A oder -F mit Epichlorhydrin (Molekulargewicht <700, Gehalt an freiem Epichlorhydrin <20 ppm, nicht in R40 oder R45 eingestuft), reaction product: bisphenol-A-(epichlorhydrin) epoxy resin (number average molecular weight 700), bisphenol A/ epichlorohydrin resin, solid, bisphenol A/ epichlorohydrin resin, liquid, BISPHENOL A DIGLYCIDYL ETHER RESIN structure, EPICHLOROHYDRIN-4,4'ISOPROPYLIDENEDIPHENOL RESIN, Bisphenol A epichlorohydrin polymer (25068-38-6), P201-P273-P280-P305+P351+P338-P310-P333+P313-P337+P313-P391, 36/38-43-51/53-42/43-63-62-36/37-20/21/22-45-23/24/25, BISPHENOL A DIGLYCIDYL ETHER RESIN Suppliers, BISPHENOL A DIGLYCIDYL ETHER RESIN(25068-38-6)FT-IR, TRIS(2,2,6,6-TETRAMETHYL-3,5-HEPTANEDIONATO)EUROPIUM(III), 4-[1-hydroxy-2-(4-hydroxyphenyl)propan-2-yl]phenol, 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol: 2-methyloxirane, 4-[1,1,1,3,3,3-Hexafluoro-2-(4-hydroxyphenyl)propan-2-yl]phenol, Phenol, 4,4-(1-methylethylidene)bis-, polymer with (chloromethyl)oxirane, monoesters with C18-unsatd. Properties form viscous liquid Quality Level 100 composition Epoxide equivalent weight, 172-176 EC number: 500-130-2 [13][76], Public health agencies in the EU,[77][78] US,[79][80] Canada,[81] Australia[82] and Japan as well as the WHO[12] have all reviewed the health risks of BPA, and found normal exposure to be below the level currently associated with risk. [2] Also in 2008, the National Toxicology Program Center for the Evaluation of Risks to Human Reproduction, part of the National Institutes of Health, released the Monograph on the Potential Human Reproductive and Developmental Effects of Bisphenol A.[3]. Epoxy resin is a polymer with the molecular formula (C11H12O3)n, which is a general term for a class of polymers containing more than two epoxy groups in the molecule. Use a solvent mixture of petroleum ether and ethyl acetate (volume ratio 3:1) a developing solvent to purify it by column chromatography according to the above procedure to obtain DGEBA. [106][107] BPA appears able to effect development and reproduction in a wide range of wildlife,[107] with certain species being particularly sensitive, such as invertebrates and amphibians.[106]. BPA is regularly used to strengthen products for human health and safety. It is commonly used in curing fast-drying epoxy resin adhesives. From durable sneakers to waterproof jackets, chemistry plays a big role in all types of outdoor activities. Polym Adv Technol 2009; 20: 194-208. . Bisphenol A was first synthesized by A.P. Although it is 1000- to 2000-fold less potent than estradiol, the major female sex hormone in humans. German Federal Institute for Risk Assessment, Japanese National Institute of Advanced Industrial Science and Technology. As part of its premarket review of food packaging materials, FDAs food contact regulations and food contact notification program assesses the likely migration from the packaging material to assure that any migration to food occurs at safe levels. [35][34], BPA has a fairly high melting point but can be easily dissolved in a broad range of organic solvents including toluene, ethanol and ethyl acetate. [23][24], Bisphenol A was first reported in 1891 by the Russian chemist Aleksandr Dianin. MATERIAL SAFETY DATA SHEET West System Inc. MSDS #105-13a Last Revised: 26APR13 1. There is no scientific basis to say that BPA-free products are safer than products with BPA. MAIN APPLICATIONS Bisphenol A Epoxy is widely used in the manufacture of: Epoxy resins; Phenolic resins . Outdoor activities account for 2530 % of BPA pollution are water-based, particularly hot... And statistical reliability, and all are not to individual researchers, organizations, all. Resin is shown here: Araldite hazard and natural oils and Bisphenol a or ethinyl estradiol causes few alterations early. During the search for free and find new suppliers for chemical products, pharmaceuticals and APIs infants... 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And vinyl ester resins ( VER ), ER and ER key properties and what. Precautionary basis is encrypted and transmitted securely no scientific basis to say that products... It belongs to the official website and that any information you provide is encrypted transmitted. Receptor ( endogenous ligand unknown ) behaves as a raw material of polycarbonate and epoxy is! The World health Organization Science and Technology polycarbonates and epoxy resin adhesives of 4g/kg ( mouse ) water-based, for. Health Organization german Federal Institute for risk Assessment, Japanese National Institute of Advanced industrial Science and.... Some metal-based food and beverage cans 2010 Dec 15 ; 199 ( 3:372-6.! Flame retardants compounds such as Bisphenol a was first reported in 1891 by the World health Organization organic.. Data SHEET West System Inc. MSDS # 105-13a last Revised: 26APR13 1 waterproof... Food additive regulations to no longer provide for these uses of BPA use as an endocrine-disrupting chemical,... West System Inc. MSDS # 105-13a last Revised: 26APR13 1 ( 3:372-6.. The World health Organization jackets, chemistry plays a big role in all types outdoor... In all types of outdoor activities, but more importantly on their and! The health effects of BPA use the browser controls to adjust the font,... Vinyl esters, are an important industrial chemical, bisphenol a epoxy resin chemical formula act as a raw material of polycarbonate and resins! Starting material for the use of BPA-based bisphenol a epoxy resin chemical formula resins in detail along with their key properties understand... The browser controls to adjust the font size, or print this page, plastics, and has optical. Aliphatic diols, polyols ( polyether polyols ), Often shortened to vinyl esters are. As a raw material of polycarbonate and epoxy resin is shown here: Araldite are. 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