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Encyclopedia > Phthalates
General chemical structure of phthalates. R and R' = CnH2n+1; n = 4-15
General chemical structure of phthalates. R and R' = CnH2n+1; n = 4-15

Phthalates, or phthalate esters, are a group of chemical compounds that are mainly used as plasticizers (substances added to plastics to increase their flexibility). They are chiefly used to turn polyvinyl chloride from a hard plastic into a flexible plastic. General phthalate structure that I cobbled together. ... General phthalate structure that I cobbled together. ... Plasticizers are additives that soften the materials (usually a plastic or a concrete mix) they are added to. ... Plastic covers a range of synthetic or semisynthetic polymerization products. ... Polyvinyl chloride, (IUPAC Polychloroethene) commonly abbreviated PVC, is a widely-used plastic. ...


Phthalate esters are the dialkyl or alkyl aryl esters of 1,2-benzenedicarboxylic acid; the name phthalate derives from phthalic acid. When added to plastics, phthalates allow the long polyvinyl molecules to slide against one another. The phthalates show low water solubility, high oil solubility, and low volatility. The polar carboxyl group contributes little to the physical properties of the phthalates, except when R and R' are very small (such as ethyl or methyl groups). They are colorless, odorless liquids produced by reacting phthalic anhydride with an appropriate alcohol (usually 6 to 13 carbon). General formula of a carboxylate ester. ... An alkyl is a univalent radical containing only carbon and hydrogen atoms arranged in a chain. ... In the context of organic molecules, aryl refers to any member of the set of functional groups or substituents that are derived from a simple aromatic ring. ... Phthalic acid, or benzene-1,2-dicarboxylic acid, is a dicarboxylic acid, with formula C6H4(COOH)2. ... Phthalic acid, or benzene-1,2-dicarboxylic acid, is an aromatic dicarboxylic acid, with formula C6H4(COOH)2. ... A carboxyl or carboxylic group is a functional group consisting of a carbon atom and an oxygen atom doubly bonded to each other. ... R-phrases , , , S-phrases , , , , , Flash point 152 °C RTECS number TI3150000 Supplementary data page Structure and properties n, εr, etc. ... In chemistry, an alcohol is any organic compound in which a hydroxyl group (-OH) is bound to a carbon atom of an alkyl or substituted alkyl group. ...


As of 2004, manufacturers produce about 400,000 tons (one billion pounds) of pthalates each year. They were first produced during the 1920s, and have been produced in large quantities since the 1950s, when PVC was introduced. The most widely used phthalates are di-2-ethyl hexyl phthalate (DEHP), diisodecyl phthalate (DIDP) and diisononyl phthalate (DINP). DEHP is the dominant plasticizer used in PVC, due to its low cost. Benzylbutylphthalate (BBzP) is used in the manufacture of foamed PVC, which is mostly used as a flooring material. Phthalates with small R and R' groups are used as solvents in perfumes and pesticides. 2004 (MMIV) was a leap year starting on Thursday of the Gregorian calendar. ... It has been suggested that this article or section be merged with Social issues of the 1920s. ... The 1950s were the decade that traditionally speaking, spanned the years 1950 through 1959. ... bis(2-ethylhexyl)phthalate Bis(2-ethylhexyl)phthalate (also BEHP, di-2-ethyl hexyl phthalate, DEHP, or dioctyl phthalate, DOP) is a phthalate , a branched-chain dioctyl ester of phthalic acid. ... Benzylbutylphthalate Benzylbutylphthalate (BBzP), also called n-butyl benzyl phthalate (BBP) or benzyl butyl phthalate, is a phthalate, an ester of phthalic acid, benzyl alcohol and n-butanol. ... A solvent is a liquid that dissolves a solid, liquid, or gaseous solute, resulting in a solution. ... Perfume is a mixture of fragrant essential oils and aroma compounds, fixatives, and solvents used to give the human body, objects, and living spaces a pleasant smell. ... A cropduster spreading pesticide. ...


Phthalates are also frequently used in nail polish, adhesives, caulk, paint pigments, and sex toys made of so-called "jelly rubber." Some vendors of jelly rubber sex toys advise covering them in condoms when used internally, due to the possible health risks. Bottle of No. ... An adhesive is a compound that adheres or bonds two items together. ... For a description of caulking in computer game creation, refer to caulking (computer games) Caulking is a process used in the sealing of the seams in wooden boats and making them watertight. ... Dried green paint Paint is the general term for a family of products used to protect and add color to an object or surface by covering it with a pigmented coating. ... A sex toy is a term for any object or device that is primarily used in facilitating human sexual pleasure. ... A sex toy is a term for any object or device that is primarily used in facilitating human sexual pleasure. ...

Contents


Health effects

Phthalates are controversial because high doses of many phthalates have shown hormonal activity in rodent studies. Studies on rodents involving large amounts of phthalates have shown damage to the liver, the kidneys, the lungs and the developing testes. On the other hand, one Japanese study involving juvenile primates (marmosets) did not observe testicular effects (Tomonari et al, The Toxicologist, 2003). Research published in 2006 by JOINT RESEARCH CENTRE Institute for Health and Consumer Protection European Chemicals Bureau has found that two of the suspected dangerous phthalates banned by EU legislation - diisononyl phthalate (DINP) and diisodecyl phthalate (DIDP) - show no risks to human health or the environment for any current use.[1] The liver is the largest internal organ of the human body. ... Human kidneys viewed from behind with spine removed The kidneys are bean-shaped excretory organs in vertebrates. ... The heart and lungs (from an older edition of Grays Anatomy) The lung is an organ belonging to the respiratory system and interfacing to the circulatory system of air-breathing vertebrates. ... Human male anatomy The testicles, known medically as testes (singular testis), are the male generative glands in animals. ... marmosts fuck all the time. ...



2004 - a joint Swedish-Danish research team found a very strong link between allergies in children and the phthalates DEHP and BBzP. bis(2-ethylhexyl)phthalate Bis(2-ethylhexyl)phthalate (also BEHP, di-2-ethyl hexyl phthalate, DEHP, or dioctyl phthalate, DOP) is a phthalate , a branched-chain dioctyl ester of phthalic acid. ... Benzylbutylphthalate Benzylbutylphthalate (BBzP), also called n-butyl benzyl phthalate (BBP) or benzyl butyl phthalate, is a phthalate, an ester of phthalic acid, benzyl alcohol and n-butanol. ...


2004 - On the other hand, a study by Children's National Medical Center and George Washington University was found no adverse effects in adolescents who had been exposed to phthalates as neonates. The study measured both physical characteristics and chemical characteristics of the subjects [2].


2005 - study reported that phthalates may mimic the female hormone oestrogen (see xenoestrogens), and cause "feminisation" of baby boys. Phthalates and Baby Boys: Potential Disruption of Human Genital Development. Barrett JR. Environ Health Perspect. 2005 Aug; 113(8): A542. Estrogens (or oestrogens) are a group of steroid compounds that function as the primary female sex hormone. ... Xenoestrogens are synthetic substances that differ from those produced by living organisms and imitate or enhance the effect of estrogens. ...



In the study by the University of Missouri in Columbia, urine samples were collected from pregnant women in four United States cities. All of the women were found to have levels of phthalate residues in their urine[citation needed]. The University of Missouri System is the designated public research and land-grant university system of the state of Missouri. ...


2005 - Upon birth of the children whose mother's urine had been previously measured, the genital features and anogenital distance were measured and correlated with the residue levels in the mother's urine. In boys, the highest levels of residue were seven times more likely to have a shortened anogenital distance [3]. There was also a correlation between heightened residue levels and smaller penis sizes. The testes of boys with smaller penises were more likely to have testes that didn't descend properly into the scrotum. The anogenital distance is a measure of feminisation measuring the distance between the anus and to the base of the penis. ...


The reaction of the public to the results study has been criticized [4]. Critics claim that the methodology used, including a small, homogeneous study group that was not pulled from a wide variety of regions, can not be used to definitively claim widespread problems related to phthalates. The criticism also states that the media overstated the findings in the report.


2006 - Two of the most commonly used phthalates (DNIP and DIDP) are declared "safe" at current levels of use by EU research scientists[5][6]. Environmental impact, chronic and acute health effects in consumers (both adults and infants) and in chemical workers, have all been assessed and found to pose no risk. The rigorous EU risk assessments, which include a high degree of conservatism and built-in safety factors, have been carried out under the strict supervision of the European Commission and provide a clear scientific evaluation on which to judge whether or not a particular substance can be safely used. The research is the culmination of ten years of study into the suspect phthalates and goes against the previous conclusions and precautionary measures adopted by the EU government.


See also

Xenoestrogens are synthetic substances that differ from those produced by living organisms and imitate or enhance the effect of estrogens. ...

References

  • Susan M. Duty, Narendra P. Singh, Manori J. Silva, Dana B. Barr, John W. Brock, Louise Ryan, Robert F. Herrick, David C. Christiani, and Russ Hauser (2003). "The relationship between environmental exposures to phthalates and DNA damage in human sperm using the neutral comet assay". Environmental Health Perspectives 111 (July): 1164-1169 Abstract.
  • Shanna H. Swan, Katharina M. Main, Fan Liu, Sara L. Stewart, Robin L. Kruse, Antonia M. Calafat, Catherine S. Mao, J. Bruce Redmon, Christine L. Ternand, Shannon Sullivan, J. Lynn Teague, and the Study for Future Families Research Team (2005). "Decrease in anogenital distance among male infants with prenatal phthalate exposure". Environmental Health Perspectives In press: Abstract.
  • Swan, S.H. 2004. Phthalates in pregnant women and children. e.hormone 2004 conference. Oct. 27-30. New Orleans.
  • Swan, S.H. et al. 2005. Decrease in anogenital distance among male infants with prenatal phthalate exposure. Environmental Health Perspectives 113:1056--1061.

External links

  • Phthalates Information Centre
  • Phthalates and PVC - the Poison Plastic
  • phthalates.org
  • Phthalates and Human Health
  • A mass spectral guide for quick identification of phthalate esters (pdf)
  • The Association between Asthma and Allergic Symptoms in Children and Phthalates in House Dust: A Nested Case-Control Study
  • 'Gender-bending' chemicals found to 'feminise' boys, New Scientist, 27 May 2005.
  • Ubiquitous Chemical Associated with Abnormal Human Reproductive Development, Scientific American, May 27 2005.
  • Toy Tantrums - The Debate Over the Safety of Phthalates, Dr. Rebecca Goldin, Jan 2006
  • DIDP, DINP, and DBP - Risk Assessment Reports by the European Chemicals Bureau (ECB).
  • Scientific facts on phthalates - summary by GreenFacts of the above ECB reports.

  Results from FactBites:
 
Phthalates - Wikipedia, the free encyclopedia (1031 words)
Phthalates, or phthalate esters, are a group of chemical compounds that are mainly used as plasticizers (substances added to plastics to increase their flexibility).
Phthalates with small R and R' groups are used as solvents in perfumes and pesticides.
Phthalates are also frequently used in nail polish, adhesives, caulk, paint pigments, and sex toys made of so-called "jelly rubber." Some vendors of jelly rubber sex toys advise covering them in condoms when used internally, due to the possible health risks.
Environmental Information - Phthalates (850 words)
Although phthalates are widely distributed in the environment, their levels are low because they are subject to rapid photochemical and biodegradation.
Phthalates are subject to both aerobic and anaerobic (in the presence, or not, of oxygen respectively) biodegradation.
Phthalates don't mimic natural oestrogens and there is no evidence to suggest that their presence in the environment reduces sperm counts in humans or wildlife
  More results at FactBites »

 
 

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