Phthalates - Knowledge

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function and metabolic homeostasis, increasing the risk of obesity. The prevalence of obesity, particularly in children, is rising, according to mounting evidence, which suggests that increased exposure to phthalates through food packaging materials is to blame. In a study conducted on schoolchildren in China, the concentration of mono-n-butyl phthalate (MnBP) was assessed in urine samples. Additionally, increased exposure to phthalates has been linked to an increase in MnBP. MnBP has been linked to significant increases in weight and obesity in schoolchildren. Significant increases in MnBP concentration were found in the study's urine samples. The disruption of the arginine and proline metabolism associated with this elevated MnBP concentration as a result of phthalate exposure is thought to be a factor in the pathophysiological changes associated with childhood obesity.

935:, PVC is unique in its acceptance of large amounts of plasticizer with gradual changes in physical properties from a rigid solid to a soft gel. Phthalates derived from alcohols with 7-13 carbon atoms occupy a privileged position as general purpose plasticizers, suitable for almost all flexible PVC applications. Phthalates larger than this have limited compatibility in PVC, with di(isotridecyl) phthalate representing the practical upper limit. Conversely, plasticizers derived from alcohols with 4-6 carbon atoms are too volatile to be used on their own, but have been used alongside other compounds as secondary plasticizers, where they improve low-temperature flexibility. Compounds derived from alcohols with 1-3 carbon atoms are not used as plasticizers in PVC at all, due excessive fuming at processing temperatures (typically 180-210 °C). 1576:

children, and 6 μg/kg bodyweight/day in adults. Infants and toddlers are at the greatest risk of exposure, because of their mouthing behavior. Body-care products containing phthalates are a source of exposure for infants. The authors of a 2008 study "observed that reported use of infant lotion, infant powder, and infant shampoo were associated with increased infant urine concentrations of , and this association is strongest in younger infants. These findings suggest that dermal exposures may contribute significantly to phthalate body burden in this population." Although they did not examine health outcomes, they noted that "Young infants are more vulnerable to the potential adverse effects of phthalates given their increased dosage per unit body surface area, metabolic capabilities, and developing endocrine and reproductive systems."

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global production of phthalates has continued to rise. In 2015 total production of was around 5.5 million tonnes, up from around 2.7 million tonnes in the 1980s. The reason for this has been the increasing size of the plasticiser market (a smaller slice of a much bigger pie), driven by increases in PVC production, which nearly doubled between 2000 and 2020. The People's Republic of China is the largest consumer, accounting for around 45% of all use. Europe and the United States together account for around 25% of use, with the remainder widely spread around the world.

1863:, has been found to interact with all three peroxisome proliferator-activated receptors (PPARs). PPARs are members of the nuclear receptor superfamily. The author of the study stated "The roles of PPARs in lipid and carbohydrate metabolism raise the question of their activation by a sub-class of pollutants, tentatively named metabolic disrupters." Phthalates belong to this class of metabolic disruptors. It is a possibility that, over many years of exposure to these metabolic disruptors, they are able to deregulate complex metabolic pathways in a subtle manner. 1572:

reported by the parents." Phthalates were found in almost every sampled home in Bulgaria. The same study found that DEHP, BBzP, and DnOP were in significantly higher concentrations in dust samples collected in homes where polishing agents were used. Data on flooring materials was collected, but there was not a significant difference in concentrations between homes where no polish was used that have balatum (PVC or linoleum) flooring and homes with wood. High frequency of dusting did decrease the concentration.

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was listed as a chemical "known to the State of California to cause cancer" This means that, starting December 2014, companies with ten or more employees manufacturing, distributing or selling the product(s) containing DINP are required to provide a clear and reasonable warning for that product. The California Office of Environmental Health Hazard Assessment, charged with maintaining the Proposition 65 list and enforcing its provisions, has implemented a "No Significant Risk Level" of 146 μg/day for DINP.

5742:"Commission Delegated Directive (EU) 2021/1978 of 11 August 2021 amending, for the purposes of adapting to scientific and technical progress, Annex IV to Directive 2011/65/EU of the European Parliament and of the Council as regards an exemption for the use of bis(2-ethylhexyl) phthalate (DEHP), butyl benzyl phthalate (BBP), dibutyl phthalate (DBP) and diisobutyl phthalate (DIBP) in spare parts recovered from and used for the repair or refurbishment of medical devices" 1580:

including, but not limited to, IV tubing, gloves, nasogastric tubes, and respiratory tubing. The Food and Drug Administration did an extensive risk assessment of phthalates in the medical setting and found that neonates may be exposed to five times greater than the allowed daily tolerable intake. This finding led to the conclusion by the FDA that, "hildren undergoing certain medical procedures may represent a population at increased risk for the effects of DEHP".

1602:, a DBP metabolite of Asacol (a particular formulation of mesalamine) can be 50 times higher than the mean of nonusers. The study showed that exposures from phthalate-containing medications can far exceed population levels from other sources. DBP in medications raises concern about health risks due to the high level of exposures associated with taking these medications, especially in vulnerable segments of the population, including pregnant women and children. 2101: 1753: 1845: 1682:

during gestation and immediately thereafter. Numerous studies on adult male humans show the similar result that phthalate exposure correlates with worsening metrics of male fertility, such as semen quality, the quantity of damaged DNA in sperm, decreased sperm motility, decreased semen volume, and other metrics. Phthalates causing harm to the male reproductive system is plausible, and continues to be researched.

262: 6111: 33: 2014:. Furthermore, the law requires the establishment of a permanent review board to determine the safety of other phthalates. Prior to this legislation, the Consumer Product Safety Commission had determined that voluntary withdrawals of DEHP and diisononyl phthalate (DINP) from teethers, pacifiers, and rattles had eliminated the risk to children, and advised against enacting a phthalate ban. 5706:"Commission Implementing Decision (EU) 2017/1210 of 4 July 2017 on the identification of bis(2-ethylhexyl) phthalate (DEHP), dibutyl phthalate (DBP), benzyl butyl phthalate (BBP) and diisobutyl phthalate (DIBP) as substances of very high concern according to Article 57(f) of Regulation (EC) No 1907/2006 of the European Parliament and of the Council (notified under document C(2017) 4462)" 1482:. DEHT and DINCH are more hydrophobic than other phthalate alternatives such as bis(2-ethylhexyl) adipate (DEHA) and diisodecyl adipate (DIDA). Since alternative plasticizers such as DEHT and DINCH are more likely to bind to organic matter and airborne particles indoors, exposure occurs primarily through food consumption and contact with dust. 1673:

studies refer to this period of fetal and postnatal development as particularly important to development, but studying this is difficult; it is obviously a huge challenge to measure endocrine disruptor exposure during fetal development and then decades later diagnosing any health problems. Additionally, endocrine disruptor exposure can transmit

1989:(CPSIA), which became public law 110–314. Section 108 of that law specified that as of February 10, 2009, "it shall be unlawful for any person to manufacture for sale, offer for sale, distribute in commerce, or import into the United States any children's toy or child care article that contains concentrations of more than 0.1 percent of" 1958:

authorisation has been granted for a specific use, however they may still be imported in consumer products. The creation of an Annex XV dossier, which could ban the import of products containing these chemicals, was being prepared jointly by the ECHA and Danish authorities, and expected to be submitted by April 2016.

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and many sodas. Products containing PETE are labeled "Type 1" (with a "1" in the recycle triangle). Although the word "phthalate" appears in the name, PETE does not use phthalates as plasticizers. The terephthalate polymer PETE and the phthalate ester plasticizers are chemically different substances.

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In many cases, there are studies that show connections between phthalates and these negative outcomes, as well as studies that show no connection; this is likely due to the research challenges outlined above, and when resolved, could show that phthalate exposure does not cause health effects, or even

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to one's offspring without them being directly exposed to the endocrine disruptors. Finally, particularly low levels of exposure may still have significant effects, and exposure to multiple endocrine disruptors across a variety of compounds (not just phthalates) may synergistically combine to cause a

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Endocrine disruptors exhibit numerous behaviors that can make studying them a challenge. There can be a lag between when someone is exposed to an endocrine disruptor and any symptoms manifesting themselves–in particular fetal and early childhood exposure may have consequences later in adulthood. Many

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caused higher presence of phthalates. "People who reported eating only a little fast food had DEHP levels that were 15.5 percent higher and DiNP levels that were 25 percent higher than those who said they had eaten none. For people who reported eating a sizable amount, the increase was 24 percent and

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is believed to be the main source of DEHP and other phthalates in the general population. Fatty foods such as milk, butter, and meats are a major source. Studies show that exposure to phthalates is greater from ingestion of certain foods, rather than exposure via water bottles as is most often first

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of the polymer and then into a melt state. This enables an intimate mix of polymer and plasticizer to be formed, and for these interactions to occur. When cooled, these interactions remain and the network of PVC chains cannot reform (as is present in unplasticized PVC, or PVC-U). The alkyl chains of

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Phthalates see use as plasticisers in various other polymers, with applications centred around coatings such as lacquers, varnishes, and paints. The addition of phthalates imparts some flexibility to these materials, reducing their tendency to chip. Phthalates derived from alcohols with between 1-4

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Exposure to phthalates is more likely in women and people of color. Differences were found between Mexican-Americans, blacks, and whites in terms of the overall risk of disturbance of glucose homeostasis. With Mexican-Americans having a fasting blood glucose (FBG) increase of 5.82 mg/dL, blacks

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1999/815/EC: Commission Decision of 7 December 1999 adopting measures prohibiting the placing on the market of toys and childcare articles intended to be placed in the mouth by children under three years of age made of soft PVC containing one or more of the substances di-iso-nonyl phthalate (DINP),

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and endocrine disruption and metabolic interference. Studies conducted on mice exposed to phthalates in utero did not result in metabolic disorder in adults. However, "in a national cross-section of U.S. men, concentrations of several prevalent phthalate metabolites showed statistically significant

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In a 2008 Bulgarian study, higher dust concentrations of DEHP were found in homes of children with asthma and allergies, compared with healthy children's homes. The author of the study stated, "The concentration of DEHP was found to be significantly associated with wheezing in the last 12 months as

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The mechanism by which phthalates and related compounds plasticize polar polymers has been a subject of intense study since the 1960s. The mechanism is one of polar interactions between the polar centres of the phthalate molecule (the C=O functionality) and the positively charged areas of the vinyl

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formulations, and there are no specific labeling requirements for phthalates. PVC plastics are typically used for various containers and hard packaging, medical tubing and bags, and are labeled "Type 3". However, the presence of phthalates rather than other plasticizers is not marked on PVC items.

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In another development in 1986, California voters approved an initiative to address their growing concerns about exposure to toxic chemicals. That initiative became the Safe Drinking Water and Toxic Enforcement Act of 1986, better known by its original name of Proposition 65. In December 2013 DINP

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In general, children's exposure to phthalates is greater than that of adults. In a 1990s Canadian study that modeled ambient exposures, it was estimated that daily exposure to DEHP was 9 μg/kg bodyweight/day in infants, 19 μg/kg bodyweight/day in toddlers, 14 μg/kg bodyweight/day in

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phthalates leached from plastics, and (3) eliminating use of any personal product such as moisturizer, perfume, or cosmetics that contain phthalates. Eliminating personal products containing phthalates can be particularly difficult or impossible due to some countries such as the United States not

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Infants and hospitalized children are particularly susceptible to phthalate exposure. Medical devices and tubing may contain 20–40% Di(2-ethylhexyl) phthalate (DEHP) by weight, which "easily leach out of tubing when heated (as with warm saline / blood)". Several medical devices contain phthalates

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The properties of the phthalate can be varied by changing the alcohol, allowing for an almost limitless range of products, although only around 30 are, or have been, commercially important. Phthalates' share of the global plasticisers market has been decreasing since around 2000. Despite this the

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In order to build up adipose tissue and establish metabolic homeostasis, it has been established that early childhood and puberty are crucial developmental stages. Exposure to endocrine disruptors, such as phthalates, during these crucial developmental stages may negatively affect adipose tissue

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A widespread concern about phthalate exposure is the possibility (though not conclusive) that it is the cause of a worldwide drop in male fertility. Studies have shown that phthalates cause abnormalities in the reproductive systems of animals, with the greatest effects when the animal is exposed

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be investigated. It criticized U.S. EPA guidances, which stipulate that, when examining cumulative effects, the chemicals examined should have similar mechanisms of action or similar structures, as too restrictive. It recommended instead that the effects of chemicals that cause similar adverse

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and it can only be used in specific cases if an authorisation has been granted; similar restrictions exist in many other jurisdictions. Despite this, the phase-out of DEHP is slow and it was still the most frequently used plasticizer in 2018, with an estimated global production of 3.24 million

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review paper from 2017 gives some advice for avoiding exposure to phthalates for concerned people; while they make pains to state that there is no evidence that shows this advice will positively affect one's health, they suggest (1) eating a balanced diet to avoid ingesting too many endocrine

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The low molecular weight products BBP, DEHP, DIBP, and DBP were added to the Candidate list of Substances for Authorisation under REACH in 2008–9, and added to the Authorisation list, Annex XIV, in 2012. This means that from February 2015 they are not allowed to be produced in the EU unless

234:, and that different populations may be more severely impacted. Higher levels of some phthalate metabolites were associated with elevated FBG, fasting insulin, and insulin resistance. Non-Hispanic black women and Hispanic women have higher levels of some phthalate metabolites. 2001:

and "it shall be unlawful for any person to manufacture for sale, offer for sale, distribute in commerce, or import into the United States any children's toy that can be placed in a child's mouth or child care article that contains concentrations of more than 0.1 percent of"

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Almost 90% of all plasticizers are used in PVC, giving this material improved flexibility and durability. The majority is used in films and cable sheathing. Flexible PVC can consist of over 85% plasticizer by mass, however unplasticized PVC (UPVC) should not contain any.

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Between 90 and 95% of all phthalates are used as plasticisers for the production of flexible PVC. They were the first commercially important compounds for this role, a historic advantage that has led to them becoming firmly embedded in flexible PVC technology. Among the

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behaviors and lower cognitive and motor development. Most common associations found in medical reports link the phthalates exposure to hyperactivity, aggression, and other adverse behaviors. Some studies have found the childhood exposure to be as early as in utero.

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having a fasting blood glucose increase of 3.63 mg/dL, and whites having a fasting blood glucose increase of 1.79 mg/dL, there was evidence of an increased risk for minorities. Overall, the study concludes that phthalates may alter glucose homeostasis and

1947:, and DBP are restricted for all toys; DINP, DIDP, and DNOP are restricted only in toys that can be taken into the mouth. The restriction states that the amount of these phthalates may not be greater than 0.1% mass percent of the plasticized part of the toy. 1544:

and DEHP, which are more prevalent in dust. A 2012 Swedish study of children found that phthalates from PVC flooring were taken up into their bodies, showing that children can ingest phthalates not only from food but also by breathing and through the skin.

1478:(DINCH) (a hydrogenated version of DINP). Both DEHT and DINCH have been used in high volumes for a variety of products used in contact with humans as alternative plasticizers for DEHP and DINP. Some of these products include medical devices, toys, and 5724:"Commission Regulation (EU) 2021/2045 of 23 November 2021 amending Annex XIV to Regulation (EC) No 1907/2006 of the European Parliament and of the Council concerning the Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH)" 942:, BBP, DBP, and DIHP have been the most important phthalates, however many of these are now facing regulatory pressure and gradual phase-outs. Almost all phthalates derived from alcohols with between 3 and 8 carbons are classed as toxic by 1412:". When added to plastics, phthalates allow the polyvinyl polymers to slide against one another. The phthalates have a clear syrupy liquid consistency and show low water solubility, high oil solubility, and low volatility. The polar 2259:

Commission Regulation (EU) No 143/2011 of 17 February 2011 amending Annex XIV to Regulation (EC) No 1907/2006 of the European Parliament and of the Council on the Registration, Evaluation, Authorisation and Restriction of Chemicals

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Kolarik B, Bornehag CG, Naydenov K, Sundell J, Stavova P, Nielsen OF (December 2008). "The concentrations of phthalates in settled dust in Bulgarian homes in relation to building characteristic and cleaning habits in the family".

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assessment found that DEHP and another phthalate product, B79P, were harmful to human health. The Canadian federal government responded by banning their use in cosmetics and restricting their use in other applications.

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outcomes should be examined cumulatively. Thus, the effect of phthalates should be examined together with other antiandrogens, which otherwise may have been excluded because their mechanisms or structure are different.

5688:"Directive 2011/65/EU of the European Parliament and of the Council of 8 June 2011 on the restriction of the use of certain hazardous substances in electrical and electronic equipment (recast) Text with EEA relevance" 1678:

greater effect. Evaluating the actual effects of a specific compound such as a particular phthalate requires examining cumulative exposure across multiple compounds, rather than evaluating one compound in isolation.

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Phthalates enter the bloodstream and disrupt sex hormone production, interfering with sexual development in infants and sexual behaviour in adults. Levels of phthalates have been dose-dependently linked to reduced

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group contributes little to the physical properties of the phthalates, except when R and R' are very small (such as ethyl or methyl groups). Phthalates are colorless, odorless liquids produced by the reaction of

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Being inexpensive, nontoxic (in an acute sense), colorless, noncorrosive, biodegradable, and with easily tuned physical properties, phthalate esters are nearly ideal plasticizers. Among the numerous alternative

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Peter M. Lorz, Friedrich K. Towae, Walter Enke, Rudolf Jäckh, Naresh Bhargava, Wolfgang Hillesheim "Phthalic Acid and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim.

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published October 12, 2021 found that high phthalate levels are weakly correlated with a greater risk of dying from any cause and with a stronger correlation to dying from heart problems, but the calculated

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Giulivo M, Lopez de Alda M, Capri E, Barceló D (November 2016). "Human exposure to endocrine disrupting compounds: Their role in reproductive systems, metabolic syndrome and breast cancer. A review".

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became the more favored plasticizer for cellulose nitrate. Phthalates were first introduced in the 1920s and quickly replaced the volatile and odorous camphor. In 1931, the commercial availability of

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Erythropel HC, Maric M, Nicell JA, Leask RL, Yargeau V (December 2014). "Leaching of the plasticizer di(2-ethylhexyl)phthalate (DEHP) from plastic containers and the question of human exposure".

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The effect of phthalates on the female reproductive system is also not fully understood yet. Current studies indicate phthalates have negative effects on folliculogenesis and steroidogenesis.

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Relatively minor amounts of some phthalates find use in personal-care items such as eye shadow, moisturizer, nail polish, liquid soap, and hair spray. Low-molecular-weight phthalates like

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that they have a much greater effect than currently predicted. In all cases, larger studies are needed to demonstrate incontrovertibly what effect phthalate exposure has on human health.

951: 3715: 1445:, phthalates are released from the plastic article by relatively gentle means. For example, they can be extracted by extraction with organic solvents and, to some extent, by handling. 1927:

A 2017 assessment found that B79P and DEHP may cause environmental damage. As of 2019, regulations to protect the environment against DEHP and B79P have not yet been put into place.

2420:"Gender and racial/ethnic differences in the associations of urinary phthalate metabolites with markers of diabetes risk: National Health and Nutrition Examination Survey 2001-2008" 1429:

chain, typically residing on the carbon atom of the carbon-chlorine bond. For this to be established, the polymer must be heated in the presence of the plasticizer, first above the

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tonnes. DINP and DIDP are used as a substitutes for DEHP in many applications, as they are not classified as hazardous. Non-phthalate plasticizers are also being increasingly used.

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Karunamoorthi K, Sabesan S (May 2010). "Laboratory evaluation of dimethyl phthalate treated wristbands against three predominant mosquito (Diptera: Culicidae) vectors of disease".

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Tickner JA, Schettler T, Guidotti T, McCally M, Rossi M (January 2001). "Health risks posed by use of Di-2-ethylhexyl phthalate (DEHP) in PVC medical devices: a critical review".

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of multiple phthalates in their urine. In February 2009, the Joint Research Centre (JRC) of the European Commission published a review of methods to measure phthalates in food.

1277:, i.e. they minimize the explosive tendencies of a family of chemical compounds that otherwise are potentially dangerous to handle. Phthalates have also been used for producing 1591:(SCHER), however, considers that, even in the case when children bite off pieces from erasers and swallow them, it is unlikely that this exposure leads to health consequences. 2113:

Only unplasticized PVC (uPVC), which is mainly used as a hard construction material, has no plasticizers. If a more accurate test is needed, chemical analysis, for example by

1906:. Later studies on primates showed that the mechanism is specific to rodents; humans are resistant to the effect. The carcinogen classification was subsequently withdrawn. 1643:

were below 2 in both cases. The study estimated that phthalates may contribute to 91,000–107,000 premature deaths each year among people aged 55–64 in the United States.

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In studies of rodents exposed to certain phthalates, high doses have been shown to change hormone levels and cause birth defects. A study in the peer-reviewed journal

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Kalyanasundaram M, Mathew N (May 2006). "N,N-diethyl phenylacetamide (DEPA): A safe and effective repellent for personal protection against hematophagous arthropods".

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Early research also shows phthalate exposure may be associated with diabetes and insulin resistance, breast cancer, obesity, metabolic disorders, and immune function.

950:(DEHP or DOP), which has long been the most widely used phthalate, with commercial production dating back to the 1930s. In the EU, the use of DEHP is restricted under 3672:

Bui TT, Giovanoulis G, Cousins AP, Magnér J, Cousins IT, de Wit CA (January 2016). "Human exposure, hazard and risk of alternative plasticizers to phthalate esters".

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Despite this, however, a number of studies have found phthalates such as DEHP in bottled water and soda. One hypothesis is that these may have been introduced during

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Phthalates act by mimicking the female hormone estrogen, which in turn inhibits production of the male hormone testosterone. As such, phthalates are considered to be

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Sathyanarayana S, Karr CJ, Lozano P, Brown E, Calafat AM, Liu F, Swan SH (February 2008). "Baby care products: possible sources of infant phthalate exposure".

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Enikeev AG, Semenov AA, Permyakov AV, Sokolova NA, Gamburg KZ, Dudareva LV (May 2019). "Biosynthesis of Ortho-Phtalic Acid Esters in Plant and Cell Cultures".

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Bi M, Liu W, Luan X, Li M, Liu M, Liu W, Cui Z (October 2021). "Production, Use, and Fate of Phthalic Acid Esters for Polyvinyl Chloride Products in China".

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the phthalate then screen the PVC chains from each other as well. They are blended within the plastic article as a result of the manufacturing process.

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di(2-ethylhexyl) phthalate (DEHP), dibutyl phthalate (DBP), di-iso-decyl phthalate (DIDP), di-n-octyl phthalate (DNOP), and butylbenzyl phthalate (BBP)

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Due to the ubiquity of plasticized plastics, the majority of people are exposed to some level of phthalates. For example, most Americans tested by the

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Nathan SS, Kalaivani K, Murugan K (October 2005). "Effects of neem limonoids on the malaria vector Anopheles stephensi Liston (Diptera: Culicidae)".

3256: 1763: 5288:"Care and feeding of the endocannabinoid system: a systematic review of potential clinical interventions that upregulate the endocannabinoid system" 1691:

There are possible (though not conclusive) associations between phthalate exposure and adverse child neurodevelopment, including the development of

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Lyche JL, Gutleb AC, Bergman A, Eriksen GS, Murk AJ, Ropstad E, et al. (April 2009). "Reproductive and developmental toxicity of phthalates".

415: 2389: 4436:"Environmental exposure to non-persistent endocrine disrupting chemicals and semen quality: An overview of the current epidemiological evidence" 5674: 3719: 3071: 2200:: video of Steve Risotto of the American Chemistry Council, uploaded by user AmericanChemistry on 23 October 2009, retrieved 23 December 2011. 3134:

Ventrice P, Ventrice D, Russo E, De Sarro G (July 2013). "Phthalates: European regulation, chemistry, pharmacokinetic and related toxicity".

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Daniels PH (December 2009). "A brief overview of theories of PVC plasticization and methods used to evaluate PVC-plasticizer interaction".

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One study, conducted between 2003 and 2010 analysing data from 9,000 individuals, found that those who reported that they had eaten at a

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David F. Cadogan and Christopher J. Howick "Plasticizers" in Ullmann's Encyclopedia of Industrial Chemistry 2000, Wiley-VCH, Weinheim.

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and have demonstrated their safety for use in current applications. They are not classified for any health or environmental effects.

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medications. These coatings protect drugs from the acidity of the stomach, but allow their release and absorption in the intestines.

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IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans Volume 29: Some industrial chemicals and dyestuffs

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Zhang H, Hua Y, Chen J, Li X, Bai X, Wang H (3 July 2018). "Organism-derived phthalate derivatives as bioactive natural products".

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Swan SH, Main KM, Liu F, Stewart SL, Kruse RL, Calafat AM, et al. (Study for Future Families Research Team) (August 2005).

4328:"Environmental exposure to di-2-ethylhexyl phthalate is associated with low interest in sexual activity in premenopausal women" 2011: 5922: 3198: 3088: 3025: 1273:. Thousands of tonnes are consumed annually for this purpose. The great advantage offered by these esters is that they are 6429: 6398: 5476: 5354:

Desvergne B, Feige JN, Casals-Casas C (May 2009). "PPAR-mediated activity of phthalates: A link to the obesity epidemic?".

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Carlstedt F, Jönsson BA, Bornehag CG (February 2013). "PVC flooring is related to human uptake of phthalates in infants".

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over health concerns. They are being replaced by higher molecular-weight phthalates as well as non-phthalic plasticizers.

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Latini G, Del Vecchio A, Massaro M, Verrotti A, De Felice C (September 2006). "Phthalate exposure and male infertility".

5131:"Neurotoxicity of Ortho-Phthalates: Recommendations for Critical Policy Reforms to Protect Brain Development in Children" 4250: 1824: 926:

Plasticised PVC has excellent electrical insulation properties and is extensively used as sheathing for wires and cables.

6129: 3645: 3273: 1796: 1627: 4877:"A critical assessment of the endocrine susceptibility of the human testis to phthalates from fetal life to adulthood" 3927:"Recent Fast Food Consumption and Bisphenol A and Phthalates Exposures among the U.S. Population in NHANES, 2003-2010" 5567: 5536: 4194: 1939:

Update on non-classified plasticisers and the European REACH Candidate Classification including pending authorisation

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The use of some phthalates has been restricted in the European Union for use in children's toys since 1999. DEHP,

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had much higher levels of two separate phthalates—DEHP and DiNP—in their urine samples. Even small consumption of

176:, not all plasticizers are phthalates. The two terms are specific and unique and cannot be used interchangeably. 6121: 2340:"Phthalate and novel plasticizer concentrations in food items from U.S. fast food chains: a preliminary analysis" 909:

The extent of this natural production is not fully known, but it may create a background of phthalate pollution.

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correlations with abnormal obesity and insulin resistance." Mono-ethylhexyl-phthalate (MEHP), a metabolite of

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are sometimes classed as phthalates, as they meet the technical definition, however, being polymeric esters of

6025:"Agency for Toxic Substances and Disease Registry-Public Health Statement for Di(2-ethylhexyl) phthalate DEHP" 4104: 3571: 6475: 6470: 5759: 2896:

Latini G, De Felice C, Verrotti A (November 2004). "Plasticizers, infant nutrition and reproductive health".

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Journal of Environmental Science and Health. Part C, Environmental Carcinogenesis & Ecotoxicology Reviews

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Various plants and microorganisms have been reported to naturally produce small amounts of phthalate esters (

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with excellent electrical insulation properties, these are used to manufacture of electronics components.

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to increase their flexibility, transparency, durability, and longevity. They are used primarily to soften

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Diamanti-Kandarakis E, Bourguignon JP, Giudice LC, Hauser R, Prins GS, Soto AM, et al. (June 2009).

2483:"Racial and ethnic variations in phthalate metabolite concentration changes across full-term pregnancies" 1887: 1860: 1726: 1533: 1367: 1246: 1242: 947: 6002: 1935: 1712:

disruptors from a single source, (2) eliminating canned or packaged food in order to limit ingestion of

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Phthalates are also found in some medications, where they are used as inactive ingredients in producing

1391: 5523: 4836:"Exposure to phthalates: reproductive outcome and children health. A review of epidemiological studies" 4110:(Report). Scientific Committee on Health and Environmental Risks, European Commission. 17 October 2008. 2258: 2197: 2124: 1792: 1556:

may be dermally absorbed. Inhalational exposure is also significant with the more volatile phthalates.

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Koo HJ, Lee BM (December 2004). "Estimated exposure to phthalates in cosmetics and risk assessment".

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and warned of health risks when children regularly suck and chew on them. The European Commission

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Phthalates are easily released into the environment. In general, they do not persist due to rapid

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Heudorf U, Mersch-Sundermann V, Angerer J (October 2007). "Phthalates: toxicology and exposure".

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Generally, the high molecular weight phthalates DINP, DIDP, and DPHP have been registered under

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National Research Council (US) Committee on the Health Risks of Phthalates (18 December 2008).

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Factor-Litvak P, Insel B, Calafat AM, Liu X, Perera F, Rauh VA, Whyatt RM (10 December 2014).

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decreased sexual desire and satisfaction in women, and malformed genital development in rats.

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Balalian AA, Whyatt RM, Liu X, Insel BJ, Rauh VA, Herbstman J, Factor-Litvak P (April 2019).

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are present in higher concentrations in air in comparison with the heavier and less volatile

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In 2008, the Danish Environmental Protection Agency (EPA) found a variety of phthalates in

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Amaral Mendes JJ (June 2002). "The endocrine disrupters: a major medical challenge".

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thought of with plastic chemicals. Low-molecular-weight phthalates such as DEP, DBP,

1525: 1397: 1394: 1351: 1331: 1298: 1278: 1254: 1211: 1203: 1176: 1148: 992: 906: 332: 255: 5938: 5383: 4820: 4128:"Medications as a potential source of exposure to phthalates in the U.S. population" 4052: 4009: 3873: 3693: 3587: 3421: 3326: 2747: 2087:

The European Parliament eliminates DIBP and other phthalates from sanitary products.

1870:

Large amounts of specific phthalates fed to rodents have been shown to damage their

1778: 1536:. Higher air temperatures result in higher concentrations of phthalates in the air. 6376: 6082: 6053: 5975: 5959: 5918: 5887: 5879: 5834: 5826: 5413: 5363: 5317: 5307: 5258: 5250: 5209: 5199: 5150: 5142: 5098: 5090: 5041: 5031: 4984: 4939: 4929: 4888: 4847: 4800: 4752: 4744: 4608: 4559: 4551: 4499: 4491: 4447: 4403: 4395: 4347: 4339: 4298: 4288: 4180: 4147: 4139: 4078: 4032: 4001: 3997: 3946: 3938: 3899: 3853: 3818: 3773: 3769: 3765: 3689: 3610: 3567: 3532: 3470: 3401: 3368: 3306: 3261: 3223: 3169: 3143: 2991: 2948: 2909: 2905: 2870: 2833: 2825: 2770: 2727: 2653: 2643: 2569: 2539: 2502: 2494: 2449: 2439: 2361: 2351: 1855: 1548: 1498: 1401: 1302: 1270: 977: 291: 223: 90: 52: 46: 36:

General chemical structure of orthophthalates. (R and R' are general placeholders.)

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H.R. 4040--110th Congress (2007): Consumer Product Safety Improvement Act of 2008

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5204: 5094: 5036: 4988: 4589:"Epigenetic transgenerational actions of endocrine disruptors and male fertility" 4082: 1595: 1250: 1238: 1207: 226:

found phthalates in all but one of the grocery store and fast foods they tested.

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Barrett ES, Parlett LE, Wang C, Drobnis EZ, Redmon JB, Swan SH (November 2014).

4126:

Hernández-Díaz S, Mitchell AA, Kelley KE, Calafat AM, Hauser R (February 2009).

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Included in the candidate list referred to as substances toxic for reproduction.

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are used as fixatives for perfumes. Dimethyl phthalate has been also used as an

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Lower-molecular-weight phthalates are being replaced in many products in the

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Roy RN (November 2020). "Bioactive natural derivatives of phthalate ester".

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Ordered by molecular weight, commercially important compounds shown in bold

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Many bio-based plasticizers based on vegetable oil have been developed.

210:

In 2021, a study looked for phthalates in 64 fast food items. Phthalate

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International Journal of Occupational Medicine and Environmental Health

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if you can. Unsourced or poorly sourced material may be challenged and

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The European Union restricted phthalates from several children's toys.

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Market trend in decreasing use of low orthophthalates including DEHP

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Phthalate esters are widely used as solvents for highly reactive

414:

Toxic to Reproduction, Endocrine Disrupting, Under assessment as

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Huang T, Saxena AR, Isganaitis E, James-Todd T (February 2014).

1609:

recommended that the cumulative effects of phthalates and other

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Wilkes CE, Summers JW, Daniels CA, Berard M (1 January 2005).

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Guarantees the sale of electronic products free of phthalates.

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Toxic to Reproduction, Endocrine Disrupting, Skin sensitising

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Journal of Exposure Science & Environmental Epidemiology

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PVC properties as a function of phthalate plasticizer level

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California Office of Environmental Health Hazard Assessment

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Zamkowska D, Karwacka A, Jurewicz J, Radwan M (July 2018).

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Environmental Science and Pollution Research International

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Unplasticized PVC (UPVC): window frames and sills, doors,

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International Journal of Hygiene and Environmental Health

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10.1603/0022-2585(2006)43[518:NPDASA]2.0.CO;2

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requiring them to be disclosed in a list of ingredients.

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Current Problems in Pediatric and Adolescent Health Care

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European Review for Medical and Pharmacological Sciences

1199:, which are used in both oil and emulsion based paints. 6022: 6009: 5996: 5945: 2895: 2477:

James-Todd TM, Meeker JD, Huang T, Hauser R, Seely EW,

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2566:

Organisation for Economic Co-operation and Development

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Scientific Committee on Health and Environmental Risks

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their properties and applications are very different.

5785:"Learn the Facts About Food Packaging and Phthalates" 5285: 4587:

Anway MD, Cupp AS, Uzumcu M, Skinner MK (June 2005).

3557: 3011: 3009: 3007: 3005: 2984:

Journal of Macromolecular Science: Part A - Chemistry

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and remote areas. They also pose no acute toxicity.

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Bansal A, Henao-Mejia J, Simmons RA (January 2018).

3495: 3253: 1720: 137: 131: 108: 102: 70: 64: 5286:McPartland JM, Guy GW, Di Marzo V (12 March 2014). 2209: 1358:in 1856 for use as the first plasticizer. In 1870, 1187:, with commonly encountered applications including 119: 93: 55: 5865: 5499:"Phthalate Substance Grouping – information sheet" 4274: 3002: 2210: 2154:1,2-Cyclohexane dicarboxylic acid diisononyl ester 1476:1,2-cyclohexane dicarboxylic acid diisononyl ester 5596:Public Concern, Not Science, Prompts Plastics Ban 5442:"Chronic Hazard Advisory on Diisononyl Phthalate" 4064: 4062: 3924: 242:Phthalates are produced industrially by the acid 214:was detected in 81 percent of the samples, while 6442: 4429: 4427: 3383: 194: 3925:Zota AR, Phillips CA, Mitro SD (October 2016). 2617: 172:(PVC). Note that while phthalates are usually 4068: 4059: 3463:Journal of the American Academy of Dermatology 3339: 3257:Ullmann's Encyclopedia of Industrial Chemistry 3216:Ullmann's Encyclopedia of Industrial Chemistry 2803: 2709: 1777:Please review the contents of the section and 1626:Toy dolls manufactured in China and seized by 6137: 6072: 5710:EUR-Lex - 32017D1210 - EN - EUR-Lex. (n.d.-b) 5124: 5122: 4833: 4730: 4473: 4471: 4424: 3885: 3883: 3743: 3213: 2095: 5399: 4778: 4776: 4533: 4531: 4529: 4527: 4525: 4523: 2121:, can establish the presence of phthalates. 674:Toxic to Reproduction, Endocrine Disrupting 546:Toxic to Reproduction, Endocrine Disrupting 439:Toxic to Reproduction, Endocrine Disrupting 260: 5866:Lovekamp-Swan T, Davis BJ (February 2003). 4915: 4874: 3460: 3104: 3102: 3100: 3081:International Agency for Research on Cancer 3043:"Uses of Phthalates and Other Plasticizers" 2930: 2390:"The Plastic Chemicals Hiding in Your Food" 1969:to ban sex toys that contained phthalates. 1540:flooring leads to higher concentrations of 1505:. Outdoor air concentrations are higher in 1264: 1234:; but their use in these is very limited. 1191:. Most phthalates are also compatible with 6144: 6130: 5663: 5464:Human risk is therefore seen as negligible 5349: 5347: 5345: 5343: 5341: 5119: 4644:"What Happens If We Hit Sperm Count Zero?" 4468: 3880: 3249: 3247: 3016:Krauskopf LG (2009). "3.13 Plasticizers". 2981: 2108:Phthalates are used in some, but not all, 2104:Some "Type 3" plastics contain Phthalates. 2021: 1404:acids); the name "phthalate" derives from 1202:Other plasticised polymer systems include 1171:carbon atoms are used as plasticisers for 201:Centers for Disease Control and Prevention 5979: 5948:"Human exposure estimates for phthalates" 5891: 5838: 5417: 5321: 5311: 5262: 5213: 5203: 5154: 5102: 5045: 5035: 4943: 4933: 4892: 4851: 4773: 4756: 4563: 4520: 4503: 4451: 4407: 4351: 4302: 4292: 4184: 4151: 3950: 3777: 3718:. University of Minnesota. Archived from 3184: 3136:Environmental Toxicology and Pharmacology 3015: 2837: 2657: 2647: 2611: 2573: 2562:"Socio-economic assessment of phthalates" 2529: 2506: 2453: 2443: 2365: 2355: 1408:, which itself is derived from the word " 1098:Wire and cable insulation, flexible pipe 785:Under assessment as Endocrine Disrupting 349:Under assessment as Endocrine Disrupting 5787:. Plasticsmythbuster.org. Archived from 4918:"The effects of phthalates on the ovary" 4105:Opinion on phthalates in school supplies 3603:Journal of Vinyl and Additive Technology 3360: 3097: 2532:Journal of Vinyl and Additive Technology 2099: 1934: 1621: 1452: 921: 759:Not classified but some uses restricted 694:Not classified but some uses restricted 302:Properties of concern for human health ( 31: 5911:American Journal of Industrial Medicine 5673:was invoked but never defined (see the 5491: 5338: 4916:Hannon PR, Flaws JA (2 February 2015). 4737:Occupational and Environmental Medicine 4641: 4248: 4121: 4119: 4117: 3974: 3972: 3970: 3739: 3737: 3600: 3440:U.S. Food and Drug Administration (FDA) 3244: 2568:. OECD Environment Working Papers: 15. 2559: 2555: 2553: 1987:Consumer Product Safety Improvement Act 1646: 1607:United States National Research Council 1488: 1165: 14: 6443: 5808: 5806: 5479:. Government of Canada. 6 October 2017 5469: 5395: 5393: 4731:Hauser R, Calafat AM (November 2005). 4667: 4216: 4214: 3846:Applied Microbiology and Biotechnology 3744:Rudel RA, Perovich LJ (January 2009). 3288: 3040: 2933:Environmental Science & Technology 2413: 2411: 6125: 5505:. Government of Canada. 12 March 2017 4696: 4537: 3667: 3665: 2863:Applied Biochemistry and Microbiology 1653:Endocrine disruptor § Phthalates 1354:plastic in 1846 led to the patent of 1330:Diallyl phthalate is used to prepare 1249:(CAP), all of which are used to make 1206:(particularly the forms used to make 892: 6399:List of environmental health hazards 5356:Molecular and Cellular Endocrinology 4114: 3967: 3734: 3674:The Science of the Total Environment 2550: 2254: 2252: 2231:participating institution membership 1746: 1630:in 2013 due to high phthalate levels 1313:. and species of mosquitoes such as 27:Any ester derived from phthalic acid 5812: 5803: 5746:EUR-Lex - 32021L1978 - EN - EUR-Lex 5728:EUR-Lex - 32021R2045 - EN - EUR-Lex 5692:EUR-Lex - 32011L0065 - EN - EUR-Lex 5668: 5390: 4211: 2760: 2698:Enter CAS No's to validate manually 2408: 2150:Non-phthalate plasticizers such as 917: 24: 6284:Miscellaneous additives incl. PHCs 5858: 5447:. 2001. p. 87. Archived from 3662: 3516: 3489: 2622:; Law, Kara Lavender (July 2017). 1628:U.S. Customs and Border Protection 905:is believed to involve a modified 25: 6487: 6103: 5952:Environmental Health Perspectives 5872:Environmental Health Perspectives 5819:Environmental Health Perspectives 5243:Environmental Health Perspectives 5135:American Journal of Public Health 4834:Jurewicz J, Hanke W (June 2011). 4281:Environmental Health Perspectives 4132:Environmental Health Perspectives 3931:Environmental Health Perspectives 3537:10.1016/j.actatropica.2005.07.002 2763:Critical Reviews in Biotechnology 2290: 2249: 1930: 1721:Endocannabinoid system disruption 1617: 1305:and is especially useful against 1124:Boots and clothing, inflatables, 6109: 5777: 5752: 5669:Cite error: The named reference 4875:Albert O, Jégou B (March 2014). 3823:10.1111/j.1600-0668.2012.00788.x 2193:ACC Addresses Phthalates Safety" 2173:Antiandrogens in the environment 1972: 1854:There may be a link between the 1843: 1751: 1742: 89: 51: 5734: 5716: 5698: 5680: 5637: 5619: 5601: 5589: 5576: 5557: 5551:"Registry of Intentions - ECHA" 5543: 5529: 5517: 5434: 5279: 5230: 5171: 5062: 5003: 4960: 4909: 4868: 4827: 4724: 4690: 4661: 4642:Halpern DN (4 September 2018). 4635: 4580: 4319: 4268: 4242: 4168: 4097: 4016: 3918: 3837: 3794: 3708: 3694:10.1016/j.scitotenv.2015.09.036 3629: 3594: 3551: 3454: 3428: 3377: 3333: 3282: 3207: 3178: 3162: 3127: 3064: 3034: 2975: 2924: 2889: 2854: 2797: 2754: 2703: 2674: 2590: 2523: 2470: 1909: 1448: 6461:Suspected testicular toxicants 4002:10.1016/j.atmosenv.2008.08.028 3770:10.1016/j.atmosenv.2008.09.025 2910:10.1016/j.reprotox.2004.05.011 2382: 2331: 2307: 2264: 2237: 2203: 2184: 1779:add the appropriate references 1218:. They are also compatible in 13: 1: 6087:10.1016/S0278-6915(02)00018-2 6023:Centers for Disease Control. 6010:Centers for Disease Control. 5997:Centers for Disease Control. 4733:"Phthalates and human health" 4544:Nature Reviews. Endocrinology 4249:LaMotte S (12 October 2021). 4179:. National Research Council. 3560:Journal of Medical Entomology 3475:10.1016/S0190-9622(97)70289-5 3373:10.1002/14356007.a20_181.pub2 3052:. ExxonMobil Chemical Company 2775:10.1080/07388551.2020.1789838 2732:10.1080/10590501.2018.1490512 2682:"Search for Chemicals - ECHA" 2246:in Collins English Dictionary 2178: 2075:endocrine disrupting chemical 1598:. Urinary concentrations of 1373: 1366:(PVC) and the development of 1288: 1068:, flexible pipe, thin films ( 237: 195:Prevalence and human exposure 6430:Toxic Substances Control Act 6389:Persistent organic pollutant 6075:Food and Chemical Toxicology 5760:"Types of Plastic - I-Cycle" 5566:Retrieved 22 December 2014 5419:10.1016/j.envint.2018.09.001 5313:10.1371/journal.pone.0089566 5205:10.1371/journal.pone.0114003 5095:10.1016/j.envres.2019.01.046 5037:10.1371/journal.pone.0114003 4989:10.1016/j.envres.2016.07.011 4083:10.1016/j.cppeds.2007.11.001 2481:, et al. (March 2017). 1961:In 2006 the Dutch office of 1709:Nature Reviews Endocrinology 766:Di(2-propylheptyl) phthalate 164:, i.e., substances added to 7: 6384:Great Pacific garbage patch 4697:Salam M (20 January 2018). 4344:10.1016/j.yhbeh.2014.10.003 4231:. July 2005. Archived from 3904:10.1016/j.ijheh.2007.07.011 3342:Journal of Cosmetic Science 3187:Plastics additives handbook 3018:Plastics additives handbook 2688:. European Chemicals Agency 2139: 1965:UK sought to encourage the 1764:reliable medical references 1568:39 percent, respectively." 1247:cellulose acetate phthalate 1243:polyvinyl acetate phthalate 948:Bis(2-ethylhexyl) phthalate 445:Di-2-methoxyethyl phthalate 10: 6492: 6425:Japan Toxic Substances Law 6220:Miscellaneous plasticizers 4922:Frontiers in Endocrinology 4453:10.13075/ijomeh.1896.01195 3148:10.1016/j.etap.2013.03.014 2357:10.1038/s41370-021-00392-8 2125:Polyethylene terephthalate 2096:Identification in plastics 1888:di(2-ethylhexyl) phthalate 1650: 1368:di(2-ethylhexyl) phthalate 1345: 1237:Phthalates can plasticise 1185:cellulose acetate butyrate 655:Di(2-ethylhexyl) phthalate 466:Butyl cyclohexyl phthalate 220:Diethylhexyl terephthalate 160:. They are mainly used as 6420:European REACH regulation 6415:California Proposition 65 6407: 6364: 6321: 6283: 6250: 6219: 6165: 6158:polyhalogenated compounds 6058:10.1016/j.tox.2006.07.011 5406:Environment International 5368:10.1016/j.mce.2009.02.017 4881:Human Reproduction Update 4853:10.2478/s13382-011-0022-2 4805:10.1080/10937400903094091 3858:10.1007/s00253-014-6183-8 3436:"Phthalates in Cosmetics" 3406:10.1007/s11356-015-5267-z 3311:10.1080/15287390490513300 3041:Godwin A (26 July 2010). 2996:10.1080/00222338108066464 2875:10.1134/S0003683819020066 2560:Holland M (6 June 2018). 2218:Oxford English Dictionary 1914: 1890:was listed as a possible 1886:. Following this result, 1770:or relies too heavily on 1214:and its co-polymers like 719:n-Octyl n-decyl phthalate 258:is illustrative of this: 218:was found in 70 percent. 5147:10.2105/AJPH.2020.306014 4935:10.3389/fendo.2015.00008 3266:10.1002/14356007.a19_199 3228:10.1002/14356007.a20_439 3174:10.1002/14356007.a20_439 1977:During August 2008, the 1474:isomeric with DEHP) and 1265:Solvent and phlegmatizer 1175:-type plastics, such as 970:Plasticizer content (% 633:Dibutoxy ethyl phthalate 6466:Suspected fetotoxicants 4749:10.1136/oem.2004.017590 4613:10.1126/science.1108190 4556:10.1038/nrendo.2016.186 4538:Braun JM (March 2017). 3982:Atmospheric Environment 3750:Atmospheric Environment 3716:"Bio-based plasticizer" 3260:. Weinheim: Wiley-VCH. 3189:(6. ed.). Munich: 2953:10.1021/acs.est.1c02374 2898:Reproductive Toxicology 2223:Oxford University Press 2073:DIBP is declared as an 2022:Legislation, additional 1636:Environmental Pollution 1072:), advertising banners 1008:Elongation at break (%) 912: 872:Diisotridecyl phthalate 6311:Perfluorooctanoic acid 6012:"Phthalate Fact Sheet" 5075:Environmental Research 4969:Environmental Research 4037:10.1542/peds.2006-3766 2649:10.1126/sciadv.1700782 2445:10.1186/1476-069X-13-6 2105: 1979:United States Congress 1940: 1631: 1458: 927: 834:Diisoundecyl phthalate 714:Toxic to Reproduction 608:Toxic to Reproduction 586:Toxic to Reproduction 566:Toxic to Reproduction 527:Butyl benzyl phthalate 505:Dicyclohexyl phthalate 500:Toxic to Reproduction 461:Toxic to Reproduction 288:Alcohol carbon number 265: 37: 5598:by Jon Hamilton, NPR. 5570:15 September 2014 at 4894:10.1093/humupd/dmt050 4671:(17 September 2018). 4496:10.1210/en.2017-00882 4332:Hormones and Behavior 3185:Krauskopf LG (2009). 3083:. 1982. p. 271. 2544:10.1002/vnl.730150306 2160:Dioctyl terephthalate 2119:liquid chromatography 2103: 1981:passed and President 1938: 1884:hepatocarcinogenicity 1651:Further information: 1625: 1503:anaerobic degradation 1468:dioctyl terephthalate 1456: 1437:Because they are not 1011:Example applications 925: 679:Di(n-octyl) phthalate 613:Butyl decyl phthalate 592:Diisoheptyl phthalate 485:Di-n-pentyl phthalate 374:Di-n-propyl phthalate 306:classification 2022) 264: 35: 6476:Endocrine disruptors 6471:Suspected teratogens 6118:at Wikimedia Commons 6018:on 29 December 2010. 5813:Sax L (April 2010). 4400:10.1210/er.2009-0002 3297:(23–24): 1901–1914. 2424:Environmental Health 2298:Pthalates Fact Sheet 1667:endocrine disruptors 1647:Endocrine disruption 1561:fast food restaurant 1489:Environmental impact 1382:usually refers to di 1166:Non-PVC Plasticisers 853:Ditridecyl phthalate 792:Diisodecyl phthalate 740:Diisononyl phthalate 699:Diisooctyl phthalate 571:Diisohexyl phthalate 551:Di-n-hexyl phthalate 423:Diisobutyl phthalate 395:Di-n-butyl phthalate 6341:Endocrine disruptor 5831:10.1289/ehp.0901253 5304:2014PLoSO...989566M 5255:10.1289/ehp.1104052 5196:2014PLoSO...9k4003F 5087:2019ER....171..416B 5028:2014PLoSO...9k4003F 4981:2016ER....151..251G 4797:2009JTEHB..12..225L 4605:2005Sci...308.1466A 4599:(5727): 1466–1469. 3994:2008AtmEn..42.8553K 3943:10.1289/ehp.1510803 3815:2013InAir..23...32C 3762:2009AtmEn..43..170R 3686:2016ScTEn.541..451B 3469:(2 Pt 1): 243–249. 3398:2016ESPR...23..455A 3303:2004JTEHA..67.1901K 2945:2021EnST...5513980B 2939:(20): 13980–13989. 2822:2016NatSR...619791T 2724:2018JESHC..36..125Z 2640:2017SciA....3E0782G 2575:10.1787/a38a0e34-en 2436:2014EnvHe..13....6H 2278:. 21 September 2015 2221:(Online ed.). 1660:anogenital distance 1600:monobutyl phthalate 1350:The development of 1316:Anopheles stephensi 964: 938:Historically DINP, 815:Diundecyl phthalate 278: 254:. The synthesis of 232:insulin sensitivity 6356:Polymer fume fever 6031:on 2 November 2019 6005:on 4 January 2010. 4703:The New York Times 3191:Carl Hanser Verlag 2810:Scientific Reports 2499:10.1038/jes.2016.2 2115:gas chromatography 2106: 1941: 1632: 1459: 1419:phthalic anhydride 1364:polyvinyl chloride 1332:vinyl ester resins 1295:dimethyl phthalate 1279:plastic explosives 1129:Extremely Flexible 993:Flexural stiffness 962: 928: 893:Natural occurrence 312:Dimethyl phthalate 273:Common Phthalates 272: 266: 248:phthalic anhydride 170:polyvinyl chloride 38: 6438: 6437: 6372:Plastic pollution 6152:Health issues of 6114:Media related to 5958:(10): A440–A442. 5764:www2.illinois.gov 5454:on 5 October 2008 5412:(Pt 1): 159–168. 4388:Endocrine Reviews 4144:10.1289/ehp.11766 3988:(37): 8553–8559. 3937:(10): 1521–1528. 3852:(24): 9967–9981. 3615:10.1002/vnl.20211 3200:978-3-446-40801-2 3090:978-92-832-1229-4 3027:978-3-446-40801-2 2830:10.1038/srep19791 2620:Jambeck, Jenna R. 2229:(Subscription or 2134:plastic recycling 2093: 2092: 2070:November 23, 2021 2040:December 14, 2005 1852: 1851: 1828: 1725:Phthalates block 1520:Because of their 1439:chemically bonded 1352:cellulose nitrate 1299:diethyl phthalate 1271:organic peroxides 1204:polyvinyl butyral 1177:cellulose acetate 1163: 1162: 1149:soft plastic bait 989: 907:Shikimate pathway 890: 889: 369:Skin sensitising 354:Diallyl phthalate 333:Diethyl phthalate 277: 256:diethyl phthalate 16:(Redirected from 6483: 6377:Rubber pollution 6227:Organophosphates 6146: 6139: 6132: 6123: 6122: 6113: 6098: 6069: 6040: 6038: 6036: 6027:. Archived from 6019: 6014:. Archived from 6006: 6001:. Archived from 5993: 5983: 5942: 5905: 5895: 5884:10.1289/ehp.5658 5853: 5852: 5842: 5810: 5801: 5800: 5798: 5796: 5781: 5775: 5774: 5772: 5770: 5756: 5750: 5749: 5738: 5732: 5731: 5720: 5714: 5713: 5702: 5696: 5695: 5684: 5678: 5672: 5667: 5661: 5660: 5658: 5656: 5651:. 1 October 2021 5641: 5635: 5634: 5623: 5617: 5616: 5605: 5599: 5593: 5587: 5580: 5574: 5561: 5555: 5554: 5547: 5541: 5540: 5533: 5527: 5521: 5515: 5514: 5512: 5510: 5495: 5489: 5488: 5486: 5484: 5473: 5467: 5466: 5461: 5459: 5453: 5446: 5438: 5432: 5431: 5421: 5397: 5388: 5387: 5351: 5336: 5335: 5325: 5315: 5283: 5277: 5276: 5266: 5234: 5228: 5227: 5217: 5207: 5175: 5169: 5168: 5158: 5126: 5117: 5116: 5106: 5066: 5060: 5059: 5049: 5039: 5007: 5001: 5000: 4964: 4958: 4957: 4947: 4937: 4913: 4907: 4906: 4896: 4872: 4866: 4865: 4855: 4831: 4825: 4824: 4780: 4771: 4770: 4760: 4728: 4722: 4721: 4719: 4717: 4694: 4688: 4687: 4685: 4683: 4665: 4659: 4658: 4656: 4654: 4639: 4633: 4632: 4584: 4578: 4577: 4567: 4535: 4518: 4517: 4507: 4475: 4466: 4465: 4455: 4431: 4422: 4421: 4411: 4379: 4366: 4365: 4355: 4323: 4317: 4316: 4306: 4296: 4294:10.1289/ehp.8100 4287:(8): 1056–1061. 4272: 4266: 4265: 4263: 4261: 4246: 4240: 4239: 4238:on 1 April 2007. 4237: 4226: 4218: 4209: 4208: 4188: 4172: 4166: 4165: 4155: 4123: 4112: 4111: 4109: 4101: 4095: 4094: 4066: 4057: 4056: 4031:(2): e260–e268. 4020: 4014: 4013: 3976: 3965: 3964: 3954: 3922: 3916: 3915: 3887: 3878: 3877: 3841: 3835: 3834: 3798: 3792: 3791: 3781: 3741: 3732: 3731: 3729: 3727: 3712: 3706: 3705: 3669: 3660: 3659: 3633: 3627: 3626: 3598: 3592: 3591: 3555: 3549: 3548: 3520: 3514: 3513: 3493: 3487: 3486: 3458: 3452: 3451: 3449: 3447: 3432: 3426: 3425: 3381: 3375: 3364: 3358: 3357: 3337: 3331: 3330: 3286: 3280: 3279: 3251: 3242: 3241: 3211: 3205: 3204: 3182: 3176: 3166: 3160: 3159: 3131: 3125: 3124: 3122: 3120: 3114:www.ceresana.com 3106: 3095: 3094: 3078: 3068: 3062: 3061: 3059: 3057: 3047: 3038: 3032: 3031: 3013: 3000: 2999: 2990:(6): 1263–1278. 2979: 2973: 2972: 2928: 2922: 2921: 2893: 2887: 2886: 2858: 2852: 2851: 2841: 2801: 2795: 2794: 2758: 2752: 2751: 2707: 2701: 2700: 2695: 2693: 2678: 2672: 2671: 2661: 2651: 2628:Science Advances 2615: 2609: 2608: 2602: 2594: 2588: 2587: 2577: 2557: 2548: 2547: 2527: 2521: 2520: 2510: 2474: 2468: 2467: 2457: 2447: 2415: 2406: 2405: 2403: 2401: 2396:. 4 January 2024 2394:Consumer Reports 2386: 2380: 2379: 2369: 2359: 2335: 2329: 2328: 2327:on 20 July 2011. 2326: 2319: 2311: 2305: 2304: 2302: 2294: 2288: 2287: 2285: 2283: 2268: 2262: 2256: 2247: 2241: 2235: 2234: 2226: 2214: 2207: 2201: 2194: 2188: 2026: 2025: 1856:obesity epidemic 1847: 1846: 1838: 1835: 1829: 1827: 1786: 1755: 1754: 1747: 1596:enteric coatings 1499:photodegradation 1309:responsible for 1303:insect repellent 1251:enteric coatings 1003:Tensile strength 987: 978:Specific gravity 965: 961: 946:. This includes 918:PVC Plasticisers 292:Molecular weight 279: 275: 271: 224:Consumer Reports 150:phthalate esters 147: 146: 143: 142: 139: 136: 133: 130: 127: 124: 121: 117: 116: 113: 110: 107: 104: 101: 98: 95: 88: 80: 79: 76: 75: 72: 69: 66: 63: 60: 57: 50: 21: 6491: 6490: 6486: 6485: 6484: 6482: 6481: 6480: 6441: 6440: 6439: 6434: 6403: 6360: 6317: 6279: 6246: 6215: 6161: 6150: 6106: 6101: 6034: 6032: 5964:10.2307/3435033 5861: 5859:Further reading 5856: 5811: 5804: 5794: 5792: 5783: 5782: 5778: 5768: 5766: 5758: 5757: 5753: 5740: 5739: 5735: 5722: 5721: 5717: 5704: 5703: 5699: 5686: 5685: 5681: 5670: 5664: 5654: 5652: 5643: 5642: 5638: 5625: 5624: 5620: 5607: 5606: 5602: 5594: 5590: 5581: 5577: 5562: 5558: 5549: 5548: 5544: 5535: 5534: 5530: 5522: 5518: 5508: 5506: 5497: 5496: 5492: 5482: 5480: 5475: 5474: 5470: 5457: 5455: 5451: 5444: 5440: 5439: 5435: 5398: 5391: 5352: 5339: 5284: 5280: 5235: 5231: 5190:(12): e114003. 5176: 5172: 5127: 5120: 5067: 5063: 5022:(12): e114003. 5008: 5004: 4965: 4961: 4914: 4910: 4873: 4869: 4832: 4828: 4781: 4774: 4743:(11): 806–818. 4729: 4725: 4715: 4713: 4695: 4691: 4681: 4679: 4666: 4662: 4652: 4650: 4640: 4636: 4585: 4581: 4536: 4521: 4476: 4469: 4432: 4425: 4380: 4369: 4324: 4320: 4273: 4269: 4259: 4257: 4247: 4243: 4235: 4224: 4220: 4219: 4212: 4197: 4173: 4169: 4124: 4115: 4107: 4103: 4102: 4098: 4067: 4060: 4021: 4017: 3977: 3968: 3923: 3919: 3888: 3881: 3842: 3838: 3799: 3795: 3742: 3735: 3725: 3723: 3722:on 6 April 2012 3714: 3713: 3709: 3670: 3663: 3648: 3634: 3630: 3599: 3595: 3556: 3552: 3521: 3517: 3494: 3490: 3459: 3455: 3445: 3443: 3434: 3433: 3429: 3382: 3378: 3365: 3361: 3338: 3334: 3287: 3283: 3276: 3252: 3245: 3238: 3212: 3208: 3201: 3193:. p. 495. 3183: 3179: 3167: 3163: 3132: 3128: 3118: 3116: 3108: 3107: 3098: 3091: 3076: 3070: 3069: 3065: 3055: 3053: 3045: 3039: 3035: 3028: 3014: 3003: 2980: 2976: 2929: 2925: 2894: 2890: 2859: 2855: 2802: 2798: 2759: 2755: 2708: 2704: 2691: 2689: 2680: 2679: 2675: 2634:(7): e1700782. 2618:Geyer, Roland; 2616: 2612: 2600: 2596: 2595: 2591: 2558: 2551: 2528: 2524: 2475: 2471: 2416: 2409: 2399: 2397: 2388: 2387: 2383: 2336: 2332: 2324: 2317: 2313: 2312: 2308: 2300: 2296: 2295: 2291: 2281: 2279: 2270: 2269: 2265: 2257: 2250: 2242: 2238: 2228: 2208: 2204: 2192: 2189: 2185: 2181: 2142: 2098: 2084:August 11, 2021 2024: 1975: 1933: 1917: 1912: 1882:also indicated 1848: 1844: 1839: 1833: 1830: 1787: 1776: 1772:primary sources 1756: 1752: 1745: 1730: 1723: 1655: 1649: 1620: 1491: 1451: 1376: 1348: 1291: 1267: 1239:ethyl cellulose 1208:laminated glass 1168: 1147:Fishing lures ( 986: 933:common plastics 920: 915: 895: 274: 240: 197: 118: 92: 83: 82: 54: 45: 44: 28: 23: 22: 15: 12: 11: 5: 6489: 6479: 6478: 6473: 6468: 6463: 6458: 6453: 6436: 6435: 6433: 6432: 6427: 6422: 6417: 6411: 6409: 6405: 6404: 6402: 6401: 6396: 6391: 6386: 6381: 6380: 6379: 6368: 6366: 6362: 6361: 6359: 6358: 6353: 6348: 6343: 6338: 6333: 6327: 6325: 6319: 6318: 6316: 6315: 6314: 6313: 6303: 6298: 6293: 6287: 6285: 6281: 6280: 6278: 6277: 6270:Vinyl chloride 6267: 6264:Polycarbonates 6256: 6254: 6248: 6247: 6245: 6244: 6238: 6229: 6223: 6221: 6217: 6216: 6214: 6213: 6208: 6203: 6197: 6192: 6186: 6181: 6175: 6173: 6163: 6162: 6149: 6148: 6141: 6134: 6126: 6120: 6119: 6105: 6104:External links 6102: 6100: 6099: 6081:(6): 781–788. 6070: 6052:(2–3): 90–98. 6041: 6020: 6007: 5994: 5943: 5917:(1): 100–111. 5906: 5878:(2): 139–145. 5862: 5860: 5857: 5855: 5854: 5825:(4): 445–448. 5802: 5791:on 6 July 2009 5776: 5751: 5733: 5715: 5697: 5679: 5662: 5636: 5618: 5600: 5588: 5582:GovTrack.us. " 5575: 5556: 5542: 5528: 5516: 5490: 5468: 5433: 5389: 5362:(1–2): 43–48. 5337: 5278: 5249:(7): 935–943. 5229: 5170: 5141:(4): 687–695. 5118: 5061: 5002: 4959: 4908: 4887:(2): 231–249. 4867: 4846:(2): 115–141. 4826: 4791:(4): 225–249. 4772: 4723: 4689: 4660: 4634: 4579: 4550:(3): 161–173. 4519: 4467: 4446:(4): 377–414. 4423: 4394:(4): 293–342. 4367: 4338:(5): 787–792. 4318: 4267: 4241: 4210: 4195: 4186:10.17226/12528 4167: 4138:(2): 185–189. 4113: 4096: 4058: 4015: 3966: 3917: 3898:(5): 623–634. 3879: 3836: 3793: 3756:(1): 170–181. 3733: 3707: 3661: 3647:978-3446227149 3646: 3628: 3609:(4): 219–223. 3593: 3566:(3): 518–525. 3550: 3515: 3504:(5): 443–448. 3488: 3453: 3427: 3392:(1): 455–468. 3376: 3359: 3348:(2): 127–137. 3332: 3281: 3275:978-3527306732 3274: 3243: 3236: 3206: 3199: 3177: 3161: 3126: 3096: 3089: 3063: 3033: 3026: 3001: 2974: 2923: 2888: 2869:(3): 294–297. 2853: 2796: 2769:(7): 913–929. 2753: 2718:(3): 125–144. 2702: 2686:echa.europa.eu 2673: 2610: 2607:. 29 May 1985. 2589: 2549: 2538:(3): 140–147. 2522: 2493:(2): 160–166. 2469: 2407: 2381: 2350:(3): 366–373. 2330: 2306: 2289: 2263: 2248: 2236: 2202: 2182: 2180: 2177: 2176: 2175: 2170: 2169: 2168: 2163: 2157: 2148: 2141: 2138: 2097: 2094: 2091: 2090: 2088: 2085: 2081: 2080: 2078: 2071: 2067: 2066: 2064: 2061: 2057: 2056: 2054: 2051: 2047: 2046: 2044: 2041: 2037: 2036: 2033: 2030: 2023: 2020: 1983:George W. Bush 1974: 1971: 1967:European Union 1932: 1931:European Union 1929: 1916: 1913: 1911: 1908: 1880:rodent studies 1878:, and initial 1850: 1849: 1842: 1840: 1759: 1757: 1750: 1744: 1741: 1728: 1722: 1719: 1675:epigenetically 1648: 1645: 1619: 1618:Health effects 1616: 1513:areas than in 1495:biodegradation 1490: 1487: 1480:food packaging 1450: 1447: 1375: 1372: 1347: 1344: 1290: 1287: 1266: 1263: 1230:, and certain 1197:acrylic resins 1181:nitrocellulose 1167: 1164: 1161: 1160: 1145: 1143: 1141: 1139: 1136: 1133: 1130: 1126: 1125: 1122: 1119: 1116: 1113: 1110: 1107: 1104: 1100: 1099: 1096: 1093: 1090: 1087: 1084: 1081: 1078: 1074: 1073: 1066:Vinyl flooring 1063: 1060: 1057: 1054: 1051: 1048: 1045: 1041: 1040: 1034: 1031: 1028: 1025: 1023: 1020: 1017: 1013: 1012: 1009: 1006: 1000: 990: 988:(type A, 15 s) 984:Shore hardness 981: 975: 968: 919: 916: 914: 911: 894: 891: 888: 887: 885: 882: 879: 876: 873: 869: 868: 866: 863: 860: 857: 854: 850: 849: 847: 844: 841: 838: 835: 831: 830: 828: 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1789:Find sources: 1784: 1780: 1774: 1773: 1769: 1765: 1760:This section 1758: 1749: 1748: 1743:Other effects 1740: 1738: 1735: 1731: 1718: 1715: 1710: 1705: 1701: 1698: 1694: 1689: 1686: 1683: 1679: 1676: 1670: 1668: 1663: 1661: 1654: 1644: 1642: 1641:hazard ratios 1637: 1629: 1624: 1615: 1612: 1611:antiandrogens 1608: 1605:In 2008, the 1603: 1601: 1597: 1592: 1590: 1586: 1581: 1577: 1573: 1569: 1566: 1562: 1557: 1555: 1550: 1546: 1543: 1539: 1535: 1531: 1527: 1523: 1518: 1516: 1512: 1508: 1504: 1500: 1496: 1486: 1483: 1481: 1477: 1473: 1472:terephthalate 1469: 1465: 1455: 1446: 1444: 1440: 1435: 1432: 1426: 1424: 1420: 1415: 1411: 1407: 1406:phthalic acid 1403: 1399: 1396: 1393: 1389: 1388:phthalic acid 1385: 1381: 1371: 1369: 1365: 1361: 1357: 1353: 1343: 1341: 1340:phthalic acid 1337: 1333: 1328: 1326: 1325: 1324:Aedes aegypti 1321: 1320:Culex pipiens 1317: 1312: 1308: 1304: 1300: 1296: 1286: 1284: 1280: 1276: 1275:phlegmatizers 1272: 1262: 1260: 1256: 1252: 1248: 1244: 1240: 1235: 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Retrieved 4254: 4244: 4233:the original 4228: 4176: 4170: 4135: 4131: 4099: 4077:(2): 34–49. 4074: 4070: 4028: 4024: 4018: 3985: 3981: 3934: 3930: 3920: 3895: 3891: 3849: 3845: 3839: 3809:(1): 32–39. 3806: 3802: 3796: 3753: 3749: 3724:. Retrieved 3720:the original 3710: 3677: 3673: 3638:PVC handbook 3637: 3631: 3606: 3602: 3596: 3563: 3559: 3553: 3531:(1): 47–55. 3528: 3525:Acta Tropica 3524: 3518: 3501: 3497: 3491: 3466: 3462: 3456: 3444:. Retrieved 3439: 3430: 3389: 3385: 3379: 3362: 3345: 3341: 3335: 3294: 3290: 3284: 3255: 3219: 3215: 3209: 3186: 3180: 3164: 3142:(1): 88–96. 3139: 3135: 3129: 3117:. Retrieved 3113: 3072: 3066: 3054:. Retrieved 3049: 3036: 3017: 2987: 2983: 2977: 2936: 2932: 2926: 2904:(1): 27–33. 2901: 2897: 2891: 2866: 2862: 2856: 2816:(1): 19791. 2813: 2809: 2799: 2766: 2762: 2756: 2715: 2711: 2705: 2697: 2690:. Retrieved 2685: 2676: 2631: 2627: 2613: 2592: 2565: 2535: 2531: 2525: 2490: 2486: 2472: 2427: 2423: 2398:. 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Retrieved 2275: 2266: 2239: 2216: 2205: 2186: 2146:Xenoestrogen 2123: 2107: 2060:July 4, 2017 2050:June 8, 2011 2016: 1976: 1960: 1956: 1949: 1942: 1926: 1918: 1910:Legal status 1869: 1865: 1853: 1831: 1821: 1814: 1807: 1800: 1793:"Phthalates" 1788: 1768:verification 1761: 1724: 1706: 1702: 1690: 1687: 1684: 1680: 1671: 1664: 1656: 1635: 1633: 1604: 1593: 1582: 1578: 1574: 1570: 1558: 1547: 1519: 1492: 1484: 1464:plasticizers 1460: 1449:Alternatives 1441:to the host 1436: 1427: 1398:terephthalic 1392:structurally 1377: 1349: 1329: 1314: 1311:Lyme disease 1307:ixodid ticks 1292: 1268: 1236: 1201: 1169: 1153:polymer clay 1070:stretch wrap 980:(20 °C) 957: 937: 929: 903:Biosynthesis 896: 797: 790: 771: 764: 745: 738: 660: 653: 532: 525: 400: 393: 267: 250:with excess 246:reaction of 241: 228: 209: 198: 178: 174:plasticizers 162:plasticizers 149: 40: 39: 29: 6408:Regulations 6260:Bisphenol A 6035:28 December 5081:: 416–427. 4975:: 251–264. 4716:15 November 4682:15 November 4653:15 November 3680:: 451–467. 3222:: 613–614. 2479:Ferguson KK 2276:www.epa.gov 2244:"phthalate" 2212:"phthalate" 2035:References 1985:signed the 1919:In 1994, a 1762:needs more 1737:antagonists 1410:naphthalene 1402:isophthalic 1245:(PVAP) and 1224:polystyrene 1189:nail polish 205:metabolites 6451:Phthalates 6445:Categories 6336:Carcinogen 6301:Organotins 6171:Phthalates 6116:Phthalates 6046:Toxicology 5671:2005/84/EC 5458:31 January 4260:12 October 4025:Pediatrics 3803:Indoor Air 3640:. Hanser. 3446:2 November 3237:3527306730 2400:17 January 2233:required.) 2179:References 1963:Greenpeace 1892:carcinogen 1834:April 2022 1804:newspapers 1734:allosteric 1522:volatility 1470:(DEHT) (a 1386:esters of 1378:Phthalate 1374:Properties 1356:castor oil 1289:Other uses 1044:Semi-rigid 1038:rigid pipe 974:by weight) 899:endogenous 884:68515-47-9 846:85507-79-5 808:26761-40-0 782:53306-54-0 756:28553-12-0 711:27554-26-3 605:41451-28-9 238:Production 41:Phthalates 6365:Pollution 6331:Teratogen 6262:(BPA, in 5675:help page 5503:canada.ca 4711:0362-4331 3726:7 October 3656:488962111 3623:137535663 2969:238422673 2883:174809331 2791:220654942 2584:134543052 2260:(‘REACH’) 1565:fast food 1173:cellulose 1157:plastisol 827:3648-20-2 661:DEHP, DOP 583:146-50-9, 244:catalysed 18:Phthalate 6346:Diabetes 6252:Monomers 6232:Adipates 6154:plastics 6095:11983272 6066:16905236 5990:11097556 5939:23676863 5931:11148020 5902:12573895 5849:20368129 5769:23 March 5655:23 March 5568:Archived 5428:30208345 5384:12880759 5376:19433246 5332:24622769 5292:PLOS ONE 5273:22398195 5224:25493564 5184:PLOS ONE 5165:33600256 5113:30731329 5056:25493564 5016:PLOS ONE 4997:27504873 4954:25699018 4903:24077978 4862:21594692 4821:28086323 4813:20183522 4767:16234408 4669:Belluz J 4621:15933200 4574:27857130 4514:29145569 4462:30160090 4418:19502515 4362:25448532 4313:16079079 4229:U.S. CDC 4205:25009926 4162:19270786 4091:18237855 4053:22218732 4045:18245401 4010:96190203 3961:27072648 3912:17889607 3874:11715151 3866:25376446 3831:22563949 3788:20047015 3702:26410720 3588:22623121 3580:16739410 3545:16112073 3510:20556923 3422:22840018 3414:26310707 3354:16688376 3327:30617587 3319:15513891 3156:23603460 3050:cpsc.gov 2961:34617437 2918:15336709 2848:26857605 2783:32683987 2748:53565519 2740:30444179 2668:28776036 2517:26860587 2464:24499162 2430:(1): 6. 2376:34702987 2166:Citrates 2140:See also 1697:autistic 1511:suburban 1443:plastics 1423:alcohols 1414:carboxyl 1395:isomeric 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