Because of these attributes, polycarbonate is used in a wide variety of common products including digital media (e.g., CDs, DVDs), electrical and electronic equipment, automobiles, sports safety equipment, reusable food and drink containers, and many other products. Bisphenol A was investigated in the 1930's during the search for synthetic estrogens. [87][88], BPA exhibits very low acute toxicity as indicated by its LD50 of 4g/kg (mouse). Bisphenol A is the chemical product of combining one acetone unit with two phenol groups. The molecular weight and the epoxy equivalent weight are controlled by the ratio of epichlorohydrin EPC:BPA. At that time, another synthetic compound, diethylstilbestrol, was determined to be more powerful than estrogen itself, so bisphenol A was not used as a synthetic estrogen. Heightened interest in the safe use of BPA in food packaging has resulted in increased public awareness as well as scientific interest. bisphenol A: [noun] an industrial chemical compound C15H16O2 that is a component especially of hard plastics (such as polycarbonate) and epoxy resins. [90] Different expression of ERR- in different parts of the body may account for variations in bisphenolA effects. BPA is an important industrial chemical, which is mainly used as a raw material of polycarbonate and epoxy resin. [105] As such, the precise effects of BPA on the growth, reproduction, and development of aquatic organism is not fully understood. Federal government websites often end in .gov or .mil. 2010 Dec 15;199(3):372-6. j) Ferguson SA, Law CD Jr, Abshire JS. Commercial production of BPA requires distillation either extraction of BPA from many resinous byproducts under high vacuum or solvent-based extraction using additional phenol followed by distillation. Update on Bisphenol A (BPA) for Use in Food Contact Applications, January 2010; March 30, 2012; Updated March 2013; July 2014; November 2014. NIEHS has a goal to ensure job opportunities and career enhancements programs for both our work force and our community. Bisphenol A (BPA) is a chemical used to make polycarbonate plastic. It belongs to the phenol class of aromatic organic compounds. The site is secure. The review was documented in four memoranda and their attachments: Strong consumer and scientific interest in the safety of BPA has prompted FDA to support additional studies to provide further information and address apparent inconsistencies in the scientific literature about BPA. [100], Once in the environment BPA is aerobically biodegraded by a wide a variety of organisms. It is alcohol, ketone and ether soluble but presents low solubility in water and carbon tetrachloride. (sometimes called a dimer) is called bisphenol F, which is an important monomer in the production of epoxy resins. The performance of specialized collections of bisphenol A epoxy resin system components in the evaluation of workers in an occupational health . 2013 Jul 1;270(1):45-59. Among the non-food sources, exposures routes include through dust,[10] thermal paper,[20] clothing,[19] dental materials,[69] and medical devices. Comparatively minor amounts of BPA are also used as additives or modifiers in some commodity plastics. 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. 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. 2011 Dec 15;207(3):298-305. f) Doerge DR, Twaddle NC, Vanlandingham M, Fisher JW. BPA can be found in a range of products, such as: plastic food storage containers, including: pitchers. BPS differentiates from BPA by possessing a sulfone group (SO 2) as the central linker of the . Among the various polymers available as resins for composites [26][27][28][29][30][31], epoxy resins are chosen because of their excellent adhesion to many substrates and their high thermal and . [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]. FDA can make regulatory changes based on new safety or usage information. According to the ratio of raw materials, the reaction conditions and adopt the same method can be obtained with different degrees of polymerization of low molecular weight viscous liquid and high . Prediction and evaluation of route dependent dosimetry of BPA in rats at different life stages using a physiologically based pharmacokinetic model. The chemical formula of Bisphenol A is C15H16O2. 1). Durable and decorative floorings, such as terrazzo flooring, chip flooring and colored aggregate flooring, are made from epoxy resins. These chemicals are commonly used to form industrial epoxy resins, plastics, and flame retardants. MAIN APPLICATIONS Bisphenol A Epoxy is widely used in the manufacture of: Epoxy resins; Phenolic resins . Epoxy resins are made by reacting epichlorohydrin (ECH) and bisphenol A to produce a different chemical substance called bisphenol A diglycidyl ether (also known as BADGE or DGEBA). Bisphenol A diglycidyl ether (DGEBA) can be called a small-molecule adhesive. MATERIAL SAFETY DATA SHEET West System Inc. MSDS #105-13a Last Revised: 26APR13 1. Properties of copolymer epoxy resins. The .gov means its official.Federal government websites often end in .gov or .mil. It is a colourless solid which is soluble in most common organic solvents, but has very poor solubility in water. As a result, many exploratory scientific studies have appeared in the public literature. Order: 200 kg Qingdao Cemo Technology Develop Co., Ltd. Products like bike helmets, police shields, reading glasses and bullet-proof glass are all shatter resistant because of BPA. Toxicol Lett. 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. Search for free and find new suppliers for chemical products, pharmaceuticals and APIs. This is called a two-step method. Global production in 2022 is expected to reach 10 million tonnes. 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. Bisphenol S (BPS) is an organic compound with the formula (HOC 6 H 4) 2 SO 2.It has two phenol functional groups on either side of a sulfonyl group. Bisphenol A (BPA) is a chemical produced in large quantities for use primarily in the production of polycarbonate plastics. Scientific Peer-Review of the Draft Assessment of Bisphenol A for Use in Food Contact Applications, 31 October 2008. 133 Cecil Street, [1] This draft assessment was reviewed by a Subcommittee of FDAs Science Board, which released its report at the end of October 2008. It is also a component in metal can coatings, which protect the food from directly contacting metal surfaces. BPA is an industrial chemical used to make polycarbonate, a hard, clear plastic, which is used in many consumer products. Bisphenol-A, commonly abbreviated as BPA, is an organic compound with the chemical formula (CH 3) 2 C (C 6 H 4 OH) 2 belonging to the group of diphenylmethane derivatives and bisphenols, with two hydroxyphenyl groups. [8], Usually, the addition of acetone takes place at the para position on both phenols, however minor amounts of the ortho-para (up to 3%) and ortho-ortho isomers are also produced, along with several other minor byproducts. As an addition to this core study, FDA is providing extra animals and tissues to a consortium of grantees [8] selected and funded by the National Institute of Environmental Health Sciences to address other critical questions. Find out about the exciting discoveries being made by NIEHS and NIEHS-supported researchers that are helping to improve health and save lives. Found that primates (including humans) of all ages effectively metabolize and excrete BPA much more rapidly and efficiently than rodents. Polycarbonate plastic made with BPA is shatter-resistant, lightweight, and has high optical clarity, similar to glass. [28][29][30] Subsequent work found that it bound to estrogen receptors tens of thousands of times more weakly than estradiol, the major natural female sex hormone. bisphenol A type Epoxy resin depending on the molecular weight and degree of polymerization n, the resin is yellow to amber transparent viscous liquid (or solid), the average molecular weight in the production of 300~700, n; 2, softening point below 50 is called low molecular weight epoxy resin (I. E. Soft resin); Molecular weight above 1000, n>2, those having a softening point above 60 C. 2010 Sep 1;247(2):158-65. d) Doerge DR, Twaddle NC, Vanlandingham M, Brown RP, Fisher JW. TM 332 epoxy resin (Dow Chemical, Midland, TX, USA) with the epoxy group content of 24.6%-25.1% and epoxy equivalent of 171-175 which is referenced as DGEBA and with ERISYS Resorcinol . PA is also used in the production of epoxy resins. [73] Concern is mostly related to its estrogen-like activity, although it can interact with other receptor systems as an endocrine-disrupting chemical. 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 . 40:35-40. Specialty Chemicals And Polymers. Polycarbonate is strong and durable, but over time it may break down from over use at high temperatures. 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. Brand Names: Not applicable . More than 140,000 products, 270,000 supply sources and 4,400 company addresses. 25085-99-8) Suppliers Limit companies to: Worldwide USA China India EMAIL INQUIRY to 13 suppliers BOC Sciences | Address: Ramsey Road, Shirley, New York 11967, USA https://www.bocsci.com | Send Inquiry | Phone: +1- (631)-485-4226 BOC Sciences is a brand of BOCSCI Inc. Bisphenol A (BPA) is an organic synthetic compound with the chemical formula (CH3)2C(C6H4OH)2 belonging to the group of diphenylmethane derivatives and bisphenols, with two hydroxyphenyl groups. [11] www.who.int/foodsafety/areas_work/chemical-risks/bisphenol/en/, An official website of the United States government, : Dont microwave polycarbonate plastic food containers. (2013) A new approach to synergize academic and guideline-compliant research: the CLARITY-BPA research program. Neurotoxicol Teratol. Chemical Economics Handbook. [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. . Products made from BPA meet high-performance demands. Cool the mixture to room temperature; add extractant toluene/water (volume ratio 2:1) and stir it at room temperature for half an hour. Demonstrated that oral BPA administration results in rapid metabolism of BPA to an inactive form. The degree to which BPA leaches from polycarbonate bottles into liquid may depend more on the temperature of the liquid or bottle, than the age of the container. If youve ever read a news article or blog post about chemicals, you may have heard the oft-cited claim that there are 84,000 chemicals in commerce but only 200 of these have been tested for safety. 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. It can also be used in the formation of solid polymeric electrolyte for potential application in electrochemical devices. Bisphenol A diglycidyl ether (DGEBA) can be called a small-molecule adhesive. [89], BisphenolA's interacts with the estrogen-related receptor (ERR-). The viscosity of the PEOs obtained in present and earlier papers was compared with conventional low molecular weight bisphenol A based epoxy resin D.E.R. 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. By 2009, FDA released reassessments of studies cited in the NTP Monograph in addition to other relevant studies that became available after the Monographs release. It is prepared by the reaction of two equivalents of phenol with one equivalent of acetone. Parents and caregivers can make the personal choice to reduce exposures of their infants and children to BPA: This content is available to use on your website. 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.
Many of these studies addressed how the body disposes of or metabolizes BPA. When the number-average molecular weight is less than 400, the main component is bisphenol A diglycidyl ether (DGEBA, relative molecular weight 340). mixing process is what I used. [92][101][102] Its half life in water has been estimated at between 4.5 and 15 days, degradation in the air is faster than this, while soil samples degrade more slowly. FDA will also continue to consult with other expert agencies in the federal government, including the National Institutes of Health (and the National Toxicology Program), the Environmental Protection Agency, the Consumer Product Safety Commission, and the Centers for Disease Control and Prevention. [27], In terms of the endocrine disruption controversy, the British biochemist Edward Charles Dodds tested BPA as an artificial estrogen in the early 1930s. 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. [15] Although the effect is very weak,[16] the pervasiveness of BPA-containing materials raises concerns, as exposure is effectively lifelong. Other Details: - Bisphenol resin is extensively used with consumer products such as applying coatings inside of food and beverage cans as this leave no bad effects or any risk of hazard to human health. It may also be used as an ingredient in some resins, which can act as a lining on the inside of some metal food and drink cans. Extensive scientific dataabout BPA provides consumers with information about BPA safety and help put public confusion about BPA into perspective: If I buy a BPA-free product, is it safer? 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A large number of ketones undergo analogous condensation reactions. 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. [12] A common criticism is that industry-sponsored trials tend to show BPA as being safer than studies performed by academic or government laboratories,[14][75] although this has also been explained in terms of industry studies being better designed. High-performance epoxy resins are used to make aircraft, cars, bicycles, boats, golf clubs, skis and snowboards durable, flexible and strong. One reason people may be concerned about BPA is because human exposure to BPA is widespread. Food Additives & Petitions. [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. It is commonly used in curing fast-drying epoxy resin adhesives. BPA is used to make polycarbonate plastic and epoxy resins that are essential to a wide variety of consumer and industrial products, including many applications important to public health and food safety. This compound is synthesized by the condensation of acetone with phenol. just looking for general information about environmental health research or the institute, this page will help. It is important to note that scientific experts at FDA, and other regulatory bodies, review the full weight of the scientific evidence when making decisions about safety. Using the data and design from the rodent subchronic study, the National Toxicology Program/Food and Drug Administration (NTP/FDA) is conducting a long-term toxicity study of BPA in rodents to assess a variety of endpoints, including novel endpoints where questions have been raised. [9][10] The remaining 5% is used as a major component of several high-performance plastics, and as a minor additive in PVC, polyurethane, thermal paper, and several other materials. Industrially, a large excess of phenol is used to ensure full condensation; the product mixture of the cumene process (acetone and phenol) may also be used as starting material. 2010 Oct 1;248(1):1-11. h) Fisher JW, Twaddle NC, Vanlandingham M, Doerge DR. Pharmacokinetic modeling: prediction and evaluation of route dependent dosimetry of bisphenol A in monkeys with extrapolation to humans. PubChem CID 24754; . 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). BPA is a starting material for the synthesis of plastics, primarily certain polycarbonates and epoxy resins, as well as some polysulfones and . Surface chemistry the study of chemical . we live in today. Also, learn about different types of resins available and how to further improve their properties. In recent years, DGEBA has been used for the inner coating of packaging materials such as canned food. The performance represented by each part of the Bisphenol A-type epoxy resin is shown here: Araldite? FDA will continue to participate in discussions with our international regulatory and public health counterparts who are also engaged in assessing the safety of BPA. 250/ Ton Get Latest Price. [1]U.S. Food and Drug Administration, Draft Assessment of Bisphenol A for Use in Food Contact Applications, 14 August 2008. 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. 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. [103], BPA is an environmental contaminant of emerging concern. 2014 May;139(1):174-97. doi: 10.1093/toxsci/kfu022. 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. Bisphenol F (BPF) based epoxy resins are more flexible than that of BPA-based epoxies. 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.. Epoxy resins have many uses including engineering applications such as electrical laminates for printed circuit boards, composites, paints and adhesives, as well as in a variety of protective coatings. Add bisphenol A and epichlorohydrin in the amount of 1:4 into a three-necked flask equipped with a reflux device, place it in a constant-temperature oil bath, melt it with 70 C of heat, and dropwise 28.57% aqueous sodium hydroxide solution with a dropping funnel, in which the ratio of the amount of sodium hydroxide and bisphenol A is 4:1. This early work underpinned the development of epoxy resins, which in turn motivated production of BPA. There is no scientific basis to say that BPA-free products are safer than products with BPA. The site is secure. Alternatively, and to a much lesser extent, BPA may be ethoxylated and then converted to its diacrylate and dimethacrylate derivatives (bis-EMA, or EBPADMA). National Advisory Environmental Health Sciences Council - Day 1. [22][17][72], The health effects of BPA have been the subject of prolonged public and scientific debate,[12][13][14] with PubMed listing more than 16,000 scientific papers as of 2022. As is the case when foods are in direct contact with any packaging material, small, measurable amounts of the packaging materials may migrate into food and can be consumed with it. In recent years, many claims have been made about the health effects of BPA. NIEHS offers a broad range of job opportunities, career enhancement programs, and research training grants and programs in environmental health sciences and administration. The internal rotation function of the ether bond increases the flexibility of the molecule, and the hydroxyl group enhances the chemical reactivity and the bonding ability, the epoxy group cross-links molecules into a three-dimensional network structure by reacting with a curing agent. In the United States, FDA is the agency charged with this review for food contact applications. Over the following decade, coatings and resins derived from similar materials were described by workers at the companies of DeTrey Freres in Switzerland and DeVoe and Raynolds in the US. Toxicol Appl Pharmacol. Pathways include photo-oxidation, or reactions with minerals such as goethite which may be present in soils and sediments. [26] The utilization of BPA further expanded with discoveries at Bayer and General Electric on polycarbonate plastics. Pharmacokinetics of bisphenol A in neonatal and adult rhesus monkeys. Published September 2022. [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. J Appl Polym Sci . Many BPA-containing materials are non-obvious but commonly encountered,[17] and include coatings for the inside of food cans,[18] clothing designs,[19] shop receipts,[20] and dental fillings. By varying the relationship between bisphenol A and epichlorohydrin, various molecular weights are obtained for the completed epoxy resin. Diglycidyl ether of bisphenol A epoxy resin (EPOLAM 2017), and 3-minomethyl-3,5,5 trimethylclohexylamine hardener (EPOLAM 2018). and epichlorohydrin. [95] Many of the largest sources of BPA pollution are water-based, particularly wastewater from industrial facilities using BPA. The conclusion is not based simply on the number of studies, but more importantly on their quality and scientific value. Poly(Bisphenol-A-co-epichlorohydrin) (PBE) is an epoxy based resin that is a phenoxy polymer derived from bisphenol A and epichlorohydrin. [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. Chemical name (IUPAC): 4,4'-Isopropylidenediphenol, oligomeric reaction products with 1 -chloro-2,3-epoxypropane, esters with acrylic acid . It is the lowest molecular weight epoxy resins, and also used as the packaging material for coatings, adhesives, insulating paints, semiconductors, and integrated circuits and other electronic components. 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. .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. Assessment of bisphenol a ( BPA ) is an important industrial chemical used to make polycarbonate bisphenol a epoxy resin chemical formula a hard clear. Pbe ) is an industrial chemical used to make polycarbonate plastic [ 11 ] www.who.int/foodsafety/areas_work/chemical-risks/bisphenol/en/, an official of... The completed epoxy resin adhesives BPA are also used as a result, exploratory! Phenol with one equivalent of acetone common organic solvents, but more importantly on their quality and scientific value health... Effectively metabolize and excrete BPA much more rapidly and efficiently than rodents ) new... 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