Based on FDAs ongoing safety review of scientific evidence, the available information continues to support the safety of BPA for the currently approved uses in food containers and packaging. [7] As the only by-product is water, it may be considered an industrial example of green chemistry. In recent years, many claims have been made about the health effects of BPA. Supplier. 2013 Feb 15;267(1):41-8. m) Twaddle NC, Churchwell MI, Vanlandingham M, Doerge DR. Quantification of deuterated bisphenol A in serum, tissues, and excreta from adult Sprague-Dawley rats using liquid chromatography with tandem mass spectrometry. Alternatively, and to a much lesser extent, BPA may be ethoxylated and then converted to its diacrylate and dimethacrylate derivatives (bis-EMA, or EBPADMA). 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. This is further confirmed by CLARITY, as the results clearly show that BPA has very little potential to cause health effects, even when people are exposed to it throughout their lives, said Steven G. Hentges, Ph.D., Polycarbonate/BPA Global Group of the American Chemistry Council (ACC). 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. Scientific research shows that in humans, BPA is quicklymetabolized and eliminated from the body it does not accumulate in blood or tissues. [95] BPA in sediment degrades most slowly of all, particularly where this is anaerobic. 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. 80-05-7 Bisphenol a with Wholesale Price Min. The synthesis of diglycidyl ether of bisphenol A (DGEBA), the most widely used epoxy resin monomer, is: 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 . BPS differentiates from BPA by possessing a sulfone group (SO 2) as the central linker of the . A resource for kids, parents, and teachers to find fun and educational materials related to health, science, and the environment Farbenindustrie reported the coupling of BPA and epichlorohydrin. Find out about the exciting discoveries being made by NIEHS and NIEHS-supported researchers that are helping to improve health and save lives. It is not a plasticizer,[11] although it is often wrongly labelled as such. This petition demonstrated, from publicly available information and information collected from industry sources, that the use of BPA-based epoxy resins as coatings in packaging for infant formula had been abandoned. The hydroxy group may be derived from aliphatic diols, polyols (polyether polyols), phenolic compounds or dicarboxylic acids. [42] This process converts the individual molecules of BPA into large polymer chains, effectively trapping them. [96] The solubility of BPA in water is low (~300g/ton of water)[2] but this is still sufficient to make it a significant means of distribution into the environment. 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. Polycarbonate plastic made with BPA is shatter-resistant, lightweight, and has high optical clarity, similar to glass. The study included an in utero phase, direct dosing to pups to mimic bottle feeding in neonates, and employed a dose range covering the low doses where effects have been previously reported in some animal studies, as well as higher doses where estrogenic effects have been measured in guideline oral studies. Table 1, Table 2 present the . Toxicol Lett. In order to formulate an epoxy adhesive, one must have either bisphenol A or bisphenol F. Bisphenol A (BPA) is generally preferred for its curing properties. Epoxy is a synthetic resin that uses two chemical components (typically diglycidyl ethers and a combination of bisphenol A and epichlorohydrin) to harden or cure. The results, released in 2018 by the U.S. National Toxicology Program, were accompanied by a statement from Dr. Stephen Ostroff, Deputy Commissioner for Foods and Veterinary Medicine at the U. S. Food and Drug Administration (FDA), saying: our initial review supports our determination that currently authorized uses of BPA continue to be safe for consumers.. Formula: CAS CAS: Chemical Abstract Service Registry Number . Epoxy resins made with BPA are tough and readily adhere to metal surfaces, making them excellent materials for protective coatings. [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. While they have high mechanical strength values similar to epoxy resins, they are easy to apply similar to unsaturated polyester resins. 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. The chemical formula of Bisphenol A is C15H16O2. Some of this is further reacted with methacrylic acid to form bis-GMA, which is used to make vinyl ester resins. This early work underpinned the development of epoxy resins, which in turn motivated production of BPA. Durable and decorative floorings, such as terrazzo flooring, chip flooring and colored aggregate flooring, are made from epoxy resins. How does BPA get into the body? [2][7] BPA is produced on an industrial scale by the condensation of phenol and acetone, and has a global production scale which is expected to reach 10 million tonnes in 2022.[8]. [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. 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. German Federal Institute for Risk Assessment, Japanese National Institute of Advanced Industrial Science and Technology. 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. When dropping is completed within half an hour, heat it for 12-24 hours under temperature 70-80C Stop the heating after bisphenol A is completely disappeared validated by TLC method. Epub 2014 Feb 4. b) Delclos KB, Camacho L, Lewis SM, Vanlandingham MM, Latendresse JR, Olson GR, Davis KJ, Patton RE, Gamboa da Costa G, Woodling KA, Bryant MS, Chidambaram M, Trbojevich R, Juliar BE, Felton RP, Thorn BT. Studies are different, and all are not of the same quality. Before sharing sensitive information, make sure you're on a federal government site. [21] BPA has been investigated by public health agencies in many countries, as well as by the World Health Organization. It is prepared by the reaction of two equivalents of phenol with one equivalent of acetone. 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. At 830C). 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. 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. The CLARITY Study, the largest study ever done on BPA and conducted by FDA experts, confirms that BPA is safe, and supports the agencys one word answer to the question: Is BPA safe?: Yes. The method is a modification of NIOSH P&CAM Epoxy resins are typically formed by the reaction of compounds containing at least two active hydrogen atoms (polyphenolic compounds, diamines, amino phenols, heterocyclic imides and amides, aliphatic diols, etc.) 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. There is some evidence that BPA exposure in infants has decreased as a result of this. Neurotoxicol Teratol. 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. To address these questions the National Toxicology Program, partnering with FDAs National Center for Toxicological Research is carrying out in-depth studies to answer key questions and clarify uncertainties about BPA. . 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. Therefore, they are effective adhesion for most substrates such as glass, ceramics, silicon wafers, and polymer materials. read more. The safety of a food additive is not relevant to FDAs determination regarding whether a certain use of that food additive has been abandoned. Paper recycling can be a major source of release when this includes thermal paper,[9][97] leaching from PVC items may also be a significant source,[93] as can landfill leachate. Diglycidyl ether of bisphenol A epoxy resin (EPOLAM 2017), and 3-minomethyl-3,5,5 trimethylclohexylamine hardener (EPOLAM 2018). These meetings are listed in the NIEHS Events Calendar and are open to the general public. [90] It can also protect it from deactivation from the SERM 4-hydroxytamoxifen (afimoxifene). It is also a component in metal can coatings, which protect the food from directly contacting metal surfaces. 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. Toxicol Sci. Chemical name Common names and synonyms CAS number EC number Concentration; 4,4'-Isopropylidenediphenol, oligomeric reaction products with 1-chloro-2,3-epoxypropane: Epoxy resins made with BPA are tough and readily adhere to metal surfaces, making them excellent materials for protective coatings. [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]. The reaction process is as follows: The health effects of BPA have been the subject of prolonged public and scientific debate. [9][10] The manufacturing of epoxy resins and vinyl ester resins account for 2530% of BPA use. Pharmacokinetics of bisphenol A in serum and adipose tissue following intravenous administration to adult female CD-1 mice. Bisphenol A diglycidyl ether (DGEBA) can be called a small-molecule adhesive. . . It is commonly used in curing fast-drying epoxy resin adhesives. [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. Product. Properties form viscous liquid Quality Level 100 composition Epoxide equivalent weight, 172-176 The results of this study showed no effects of BPA at any dose in the low-dose range. In particular, infants are considered to be at greater risk,[83] leading to bans on the use of BPA in baby bottles and related products by the US,[84] Canada,[85] and EU[86] amongst others. [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 can be seen from above, the product is bisphenol A diglycidyl ether when there is sufficient epichlorohydrin and enough sodium hydroxide as the catalyst. Bisphenol A (BPA) is a chemical used to make polycarbonate plastic. [36] It may be purified by recrystallisation from acetic acid with water. Our line of powerful Liquid Epoxy Resins -including Bisphenol A, Modified Bisphenol A, Bisphenol A/F, Modified Bisphenol A/F, Bisphenol F offers the reliability, protection and performance you need, backed by the local customer support Only Olin can provide, virtually anywhere in the world. Released in 2018 by the U.S. National Toxicology Program, the data supports FDAs one word answer to the question Is BPA safe?: Yes. [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. [33] An excess of phenol is used to ensure full condensation and to limit the formation of byproducts, such as Dianin's compound. The IUPAC name for an epoxide group is an oxirane.. Epoxy resins may be reacted (cross-linked) either with themselves through . NIEHS provides many opportunities for funding to individual researchers, organizations, and businesses. 506 epoxy resin has been used as an embedding medium for microscopy. Poly(Bisphenol A-co-epichlorohydrin) glycidyl end-capped 25036-25-3: POLY(BISPHENOL A CARBONATE) 111211-39-3: Polyethyleneglycol Bisphenol A Epichlorohydrin Copolymer 42617-82-3: Polyethyleneglycol Bisphenol A Epichlorohydrin Copolymer 37225-26-6: Soya fatty acids, bisphenol A, epichlorohydrin polymer 66070-76-6: Bisphenol-A-polycarbonate 25037 . [98], In all cases, wastewater treatment can be highly effective at removing BPA, giving reductions of 9198%. Polym Adv Technol 2009; 20: 194-208. . Advantage Description. Name: Bisphenol A epoxy diacrylate . 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). Use the browser controls to adjust the font size, or print this page. 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. Its chemical formula is (CH3)2C (C6H4OH)2. Uses of all substances that migrate from packaging into food,. Bisphenol-F can further link generating tri- and tetra-and higher phenol oligomers. Its current uses are as a primary monomer in polycarbonate plastic and epoxy resins. NIEHS is committed to conducting the most rigorous research in environmental health sciences, and to communicating the results of this research to the public. It is alcohol, ketone and ether soluble but presents low solubility in water and carbon tetrachloride. In July, 2012, FDA took this action in response to a food additive petition filed by the American Chemistry Council (ACC) [9]. Watch Tutorial: How to Select the Best Curing Agent for Epoxy Systems. Bisphenol A (BPA) is a chemical produced in large quantities for use primarily in the production of polycarbonate plastics. Chemical Identity. [1] This draft assessment was reviewed by a Subcommittee of FDAs Science Board, which released its report at the end of October 2008. Alternatively, bisphenol A (BPA) definition is that it is a synthetically obtained colourless crystalline organic compound that occurs in the solid phase belonging to the diphenylmethane group and is soluble in organic solvents but poorly dissolves in water (0.344 % wt. Bisphenol A epoxy resin is the most common type for concrete coatings because of its excellent adhesion, toughness, abrasion resistance, and chemical resistance. 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. 2011 Sep 15;255(3):261-70. e) Doerge DR, Twaddle NC, Vanlandingham M, Fisher JW. 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. The site is secure. Its optical clarity allows direct observation of blood or other fluids to monitor proper flow. BPA's largest single application is as a co-monomer in the production of polycarbonates, which accounts for 6570% of all BPA production. Some, but not all, plastics that are marked with recycle codes 3 or 7 may be made with BPA. bisphenol A (BPA), a colourless crystalline solid belonging to the family of organic compounds; its molecular formula is C 15 H 16 O 2. Toxicol Sci. Toxicol Appl Pharmacol. It is also known to exhibit strong endocrine-disrupting ability. We provide Bisphenol A epoxy resin safety data sheet view and download for free at Echemi.com. Chemical name (IUPAC): 4,4'-Isopropylidenediphenol, oligomeric reaction products with 1 -chloro-2,3-epoxypropane, esters with acrylic acid . Update on Bisphenol A (BPA) for Use in Food Contact Applications, January 2010; March 30, 2012; Updated March 2013; July 2014; November 2014. Toxicity evaluation of bisphenol a administered by gavage to sprague dawley rats from gestation day 6 through postnatal day 90. [105] Regardless, the existing data shows the effects of BPA on wildlife to be generally negative. [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. . (2013) A new approach to synergize academic and guideline-compliant research: the CLARITY-BPA research program. Dianin in 1891. You may have heard claims that BPA exposure causes health effects in people. Regardless, due to the scientific uncertainty, many jurisdictions have taken steps to reduce exposure on a precautionary basis. BPA Initiatives - The National Institute of Environmental Health Sciences (NIEHS) and National Toxicology Program (NTP) have developed an integrated, multipronged, consortium-based approach to optimize BPA-focused research investments to more effectively address data gaps and inform decision making. 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. NIEHS sponsors and co-sponsors scientific meetings, conferences, and events throughout the year. Bisphenol A Epoxy Resin (CAS No. 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. This compound is synthesized by the condensation of acetone with phenol. By varying the relationship between bisphenol A and epichlorohydrin, various molecular weights are obtained for the completed epoxy resin. In recent years, DGEBA has been used for the inner coating of packaging materials such as canned food. What chemicals are in epoxy resin when you consider this? Abiotic degradation has been reported, but is generally slower than biodegradation. [27], In terms of the endocrine disruption controversy, the British biochemist Edward Charles Dodds tested BPA as an artificial estrogen in the early 1930s. More than 140,000 products, 270,000 supply sources and 4,400 company addresses. Excessive amounts of bisphenol A generate linear high molecular compounds with hydroxyl-, etherand epoxy-terminated groups. Bisphenol A was investigated in the 1930's during the search for synthetic estrogens. Before sharing sensitive information, make sure youre on a federal government site. [103], BPA is an environmental contaminant of emerging concern. The studies reviewed were published or available from November 1, 2009 to July 23, 2013. 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