Polycarbonate

(Redirected fromLexan)

Polycarbonates(PC) are a group ofthermoplasticpolymers containingcarbonate groupsin their chemical structures. Polycarbonates used in engineering are strong,toughmaterials, and some grades are optically transparent. They are easily worked,molded,andthermoformed.Because of these properties, polycarbonates find many applications. Polycarbonates do not have a uniqueresin identification code (RIC)and are identified as "Other", 7 on the RIC list. Products made from polycarbonate can contain the precursor monomerbisphenol A(BPA).

Polycarbonate
Repeating chemical structure unit of
Polycarbonatemade frombisphenol A
Transmission spectrumof polycarbonate
Physical properties
Density(ρ)1.20–1.22 g/cm3
Abbe number(V)34.0
Refractive index(n)1.584–1.586
FlammabilityHB-V2
Limiting oxygen index25–29%
Water absorptionEquilibrium(ASTM)0.16–0.35%
Water absorption—over 24 hours0.1%
Ultraviolet(1–380 nm)resistanceFair
Mechanical properties
Young's modulus(E)2.0–2.4GPa
Tensile strength(σt)55–75MPa
Elongation(ε)atbreak80–150%
Compressive strength(σc)>80 MPa
Poisson's ratio(ν)0.37
HardnessRockwellM70
Izod impact strength600–850J/m
Notch test20–35kJ/m2
Abrasive resistanceASTMD104410–15mg/1000cycles
Coefficient of friction(μ)0.31
Speed of sound2270 m/s
Thermal properties
Glass transition temperature(Tg)147 °C (297 °F)
Heat deflection temperature
  • 0.45 MPa: 140 °C (284 °F)
  • 1.8 MPa: 128–138 °C (262–280 °F)
Vicat softening pointat 50N145–150 °C (293–302 °F)[1]
Upper working temperature115–130 °C (239–266 °F)
Lower working temperature−40 °C (−40 °F)[2]
Thermal conductivity(k)at 23 °C0.19–0.22W/(m·K)
Thermal diffusivity(a)at 25 °C0.144 mm²/s[3]
Linear thermal expansion coefficient(α)65–70 × 10−6/K
Specific heat capacity(c)1.2–1.3 kJ/(kg·K)
Electrical properties
Dielectric constant(εr)at 1 MHz2.9
Permittivity(ε)2.568 × 10−11F/m
Relative permeability(μr)at 1 MHz0.866(2)
Permeability(μ)at 1 MHz1.089(2)μN/A2
Dissipation factorat 1MHz0.01
Surfaceresistivity1015Ω/sq
Volumeresistivity(ρ)1012–1014Ω·m
Chemical resistance
AcidsconcentratedPoor
AcidsdiluteGood
AlcoholsGood
AlkalisGood-Poor
Aromatic hydrocarbonsPoor
GreasesandoilsGood-fair
Halogenated hydrocarbonsGood-poor
HalogensPoor
KetonesPoor
Gas permeationat 20 °C
Nitrogen10–25 cm3·mm/(m2·day·Bar)
Oxygen70–130 cm3·mm/(m2·day·Bar)
Carbon dioxide400–800 cm3·mm/(m2·day·Bar)
Water vapour1–2 g·mm/(m2·day) @ 85%–0%RHgradient
Economics
Price2.6–2.8 €/kg[4]

Structure

edit
Structure of dicarbonate (PhOC(O)OC6H4)2CMe2derived from bis(phenol-A) and two equivalents of phenol.[5]This molecule reflects a subunit of a typical polycarbonate derived from bis(phenol-A).

Carbonate esters have planar OC(OC)2cores, which confer rigidity. The unique O=C bond is short (1.173 Å in the depicted example), while the C-O bonds are more ether-like (the bond distances of 1.326 Å for the example depicted). Polycarbonates received their name because they arepolymerscontainingcarbonate groups(−O−(C=O)−O−). A balance of useful features, including temperature resistance, impact resistance and optical properties, positions polycarbonates betweencommodity plasticsandengineering plastics.

Production

edit

Phosgene route

edit

The main polycarbonate material is produced by the reaction ofbisphenol A(BPA) andphosgeneCOCl
2
.The overall reaction can be written as follows:

The first step of the synthesis involves treatment of bisphenol A withsodium hydroxide,whichdeprotonatesthehydroxyl groupsof the bisphenol A.[6]

(HOC6H4)2CMe2+ 2 NaOH → Na2(OC6H4)2CMe2+ 2 H2O

The diphenoxide(Na2(OC6H4)2CMe2) reacts with phosgene to give achloroformate,which subsequently is attacked by another phenoxide. The net reaction from the diphenoxide is:

Na2(OC6H4)2CMe2+ COCl2→ 1/n [OC(OC6H4)2CMe2]n+ 2 NaCl

In this way, approximately one billion kilograms of polycarbonate is produced annually. Many otherdiolshave been tested in place of bisphenol A, e.g. 1,1-bis(4-hydroxyphenyl)cyclohexane anddihydroxybenzophenone.The cyclohexane is used as a comonomer to suppress crystallisation tendency of the BPA-derived product.Tetrabromobisphenol Ais used to enhance fire resistance.Tetramethylcyclobutanediolhas been developed as a replacement for BPA.[6]

Transesterification route

edit

An alternative route to polycarbonates entailstransesterificationfrom BPA anddiphenyl carbonate:

(HOC6H4)2CMe2+ (C6H5O)2CO → 1/n [OC(OC6H4)2CMe2]n+ 2 C6H5OH[6]

Properties and processing

edit

Polycarbonate is a durable material. Although it has high impact-resistance, it has low scratch-resistance. Therefore, a hard coating is applied to polycarbonateeyewearlensesand polycarbonate exterior automotive components. The characteristics of polycarbonate compare to those ofpolymethyl methacrylate(PMMA, acrylic), but polycarbonate is stronger and will hold up longer to extreme temperature. Thermally processed material is usually totally amorphous,[7]and as a result is highlytransparenttovisible light,with better light transmission than many kinds of glass.

Polycarbonate has aglass transition temperatureof about 147 °C (297 °F),[8]so it softens gradually above this point and flows above about 155 °C (311 °F).[9]Tools must be held at high temperatures, generally above 80 °C (176 °F) to make strain-free and stress-free products. Lowmolecular massgrades are easier to mold than higher grades, but their strength is lower as a result. The toughest grades have the highest molecular mass, but are more difficult to process.

Unlike most thermoplastics, polycarbonate can undergo large plastic deformations without cracking or breaking. As a result, it can be processed and formed at room temperature usingsheet metaltechniques, such as bending on abrake.Even for sharp angle bends with a tight radius, heating may not be necessary. This makes it valuable in prototyping applications where transparent or electrically non-conductive parts are needed, which cannot be made from sheet metal.PMMA/Acrylic,which is similar in appearance to polycarbonate, is brittle and cannot be bent at room temperature.

Main transformation techniques for polycarbonate resins:

  • extrusioninto tubes, rods and other profiles including multiwall
  • extrusion with cylinders (calenders) into sheets (0.5–20 mm (0.020–0.787 in)) and films (below 1 mm (0.039 in)), which can be used directly or manufactured into other shapes usingthermoformingor secondaryfabricationtechniques, such as bending, drilling, or routing. Due to its chemical properties it is not conducive to laser-cutting.
  • injection moldinginto ready articles

Polycarbonate may becomebrittlewhen exposed to ionizing radiation above25kGy(kJ/kg).[10]

A bottle made from polycarbonate

Applications

edit

Electronic components

edit

Polycarbonate is mainly used for electronic applications that capitalize on its collective safety features. A good electrical insulator with heat-resistant and flame-retardant properties, it is used in products associated with power systems and telecommunications hardware. It can serve as adielectricin high-stabilitycapacitors.[6]Commercial manufacture of polycarbonate capacitors mostly stopped after sole manufacturerBayer AGstopped making capacitor-grade polycarbonate film at the end of 2000.[11][12]

Construction materials

edit
Polycarbonate sheeting in a greenhouse

The second largest consumer of polycarbonates is the construction industry, e.g. for domelights, flat or curved glazing, roofing sheets andsound walls. Polycarbonates are used to create materials used in buildings that must be durable but light.

3D printing

edit

Polycarbonates are used extensively in 3D FDM printing, producing durable strong plastic products with a high melting point. Polycarbonate is relatively difficult for casual hobbyists to print compared to thermoplastics such asPolylactic acid(PLA) orAcrylonitrile butadiene styrene(ABS) because of the high melting point, difficulty with print bed adhesion, tendency to warp during printing, and tendency to absorb moisture in humid environments. Despite these issues, 3D printing using polycarbonates is common in the professional community.

Data storage

edit

A major polycarbonate market is the production ofcompact discs,DVDs,andBlu-raydiscs.[13]These discs are produced by injection-molding polycarbonate into a mold cavity that has on one side a metal stamper containing a negative image of the disc data, while the other mold side is a mirrored surface. Typical products of sheet/film production include applications in advertisement (signs, displays, poster protection).[6]

Automotive, aircraft, and security components

edit

In the automotive industry, injection-molded polycarbonate can produce very smooth surfaces that make it well-suited forsputter depositionorevaporation depositionof aluminium without the need for a base-coat. Decorative bezels and optical reflectors are commonly made of polycarbonate. Its low weight and high impact resistance have made polycarbonate the dominant material for automotive headlamp lenses. However, automotive headlamps require outer surface coatings because of its low scratch resistance and susceptibility to ultraviolet degradation (yellowing). The use of polycarbonate in automotive applications is limited to low stress applications. Stress from fasteners,plastic weldingand molding render polycarbonate susceptible tostress corrosion crackingwhen it comes in contact with certain accelerants such as salt water andplastisol.It can be laminated to makebullet-proof "glass",although "bullet-resistant" is more accurate for the thinner windows, such as are used in bullet-resistant windows in automobiles. The thicker barriers of transparent plastic used in teller's windows and barriers in banks are also polycarbonate.

So-called "theft-proof" large plastic packaging for smaller items, which cannot be opened by hand, is typically made from polycarbonate.

Lockheed Martin F-22 cockpit canopy

The cockpit canopy of theLockheed Martin F-22 Raptorjet fighter is fabricated from high optical quality polycarbonate. It is the largest item of its type.[14][15]

Niche applications

edit

Polycarbonate, being a versatile material with attractive processing and physical properties, has attracted myriad smaller applications. The use of injection molded drinking bottles, glasses and food containers is common, but the use of BPA in the manufacture of polycarbonate has stirred concerns (seePotential hazards in food contact applications), leading to development and use of "BPA-free" plastics in various formulations.

Laboratory safety goggles

Polycarbonate is commonly used in eye protection, as well as in other projectile-resistant viewing and lighting applications that would normally indicate the use ofglass,but require much higher impact-resistance. Polycarbonate lenses also protect the eye fromUVlight. Many kinds of lenses are manufactured from polycarbonate, including automotive headlamp lenses, lighting lenses,sunglass/eyeglasslenses,camera lenses,swimming goggles and SCUBA masks, and safety glasses/goggles/visors including visors in sporting helmets/masks and policeriot gear(helmet visors, riot shields, etc.). Windscreens in small motorized vehicles are commonly made of polycarbonate, such as for motorcycles, ATVs, golf carts, and small airplanes and helicopters.

The light weight of polycarbonate as opposed to glass has led to development of electronic display screens that replace glass with polycarbonate, for use in mobile and portable devices. Such displays include newere-inkand some LCD screens, though CRT, plasma screen and other LCD technologies generally still require glass for its higher melting temperature and its ability to be etched in finer detail.

As more and more governments are restricting the use of glass in pubs and clubs due to the increased incidence ofglassings,polycarbonate glasses are becoming popular for serving alcohol because of their strength, durability, and glass-like feel.[16][17]

Lamy 2000piston filler made of polycarbonate and stainless steel, launched in 1966 and still in production

Other miscellaneous items include durable, lightweight luggage,MP3/digital audio player cases,ocarinas,computer cases,riot shields,instrument panels, tealight candle containers and food blender jars. Many toys and hobby items are made from polycarbonate parts, like fins, gyro mounts, and flybar locks inradio-controlled helicopters,[18]and transparentLEGO(ABSis used for opaque pieces).[19]

Standard polycarbonate resins are not suitable for long term exposure to UV radiation. To overcome this, the primary resin can have UV stabilisers added. These grades are sold as UV stabilized polycarbonate to injection moulding and extrusion companies. Other applications, including polycarbonate sheets, may have the anti-UV layer added as a special coating or acoextrusionforenhanced weatheringresistance.

Polycarbonate is also used as a printing substrate fornameplateand other forms of industrial grade under printed products. The polycarbonate provides a barrier to wear, the elements, and fading.

Medical applications

edit

Many polycarbonate grades are used in medical applications and comply with both ISO 10993-1 and USP Class VI standards (occasionally referred to as PC-ISO). Class VI is the most stringent of the six USP ratings. These grades can be sterilized using steam at 120 °C,gamma radiation,or by theethylene oxide(EtO) method.[20]Trinseo strictly limits all its plastics with regard to medical applications.[21][22]Aliphatic polycarbonates have been developed with improved biocompatibility and degradability for nanomedicine applications.[23]

Mobile phones

edit

Some smartphone manufacturers use polycarbonate. Nokia used polycarbonate in their phones starting with theN9's unibody case in 2011. This practice continued with various phones in theLumia series.Samsung started using polycarbonate withGalaxy S III'shyperglaze-branded removable battery cover in 2012. This practice continues with various phones in theGalaxyseries. Apple started using polycarbonate with theiPhone 5C'sunibodycase in 2013.

Benefits over glass and metal back covers include durability against shattering (advantage over glass), bending and scratching (advantage over metal), shock absorption, low manufacturing costs, and no interference with radio signals andwireless charging(advantage over metal).[24] Polycarbonate back covers are available in glossy or mattesurface textures.[24]

History

edit

Polycarbonates were first discovered in 1898 byAlfred Einhorn,a German scientist working at theUniversity of Munich.[25]However, after 30 years' laboratory research, this class of materials was abandoned without commercialization. Research resumed in 1953, whenHermann SchnellatBayerin Uerdingen, Germany patented the first linear polycarbonate. The brand name "Makrolon" was registered in 1955.[26]

Also in 1953, and one week after the invention at Bayer,Daniel FoxatGeneral Electric(GE) in Pittsfield, Massachusetts, independently synthesized abranchedpolycarbonate. Both companies filed for U.S. patents in 1955, and agreed that the company lacking priority would be granted a license to the technology.[27][28]

Patent priority was resolved in Bayer's favor, and Bayer began commercial production under the trade name Makrolon in 1958. GE began production under the name Lexan in 1960, creating theGE Plasticsdivision in 1973.[29]

After 1970, the original brownish polycarbonate tint was improved to "glass-clear".

Potential hazards in food contact applications

edit

The use of polycarbonate containers for the purpose of food storage is controversial. The basis of this controversy is their hydrolysis (degradation by water, often referred to as leaching) occurring at high temperature, releasesbisphenol A:

1/n [OC(OC6H4)2CMe2]n+ H2O → (HOC6H4)2CMe2+ CO2

More than 100 studies have explored the bioactivity of bisphenol A derived from polycarbonates. Bisphenol A appeared to be released from polycarbonate animal cages into water at room temperature and it may have been responsible for enlargement of the reproductive organs of female mice.[30]However, the animal cages used in the research were fabricated from industrial grade polycarbonate, rather than FDA food grade polycarbonate.

An analysis of the literature on bisphenol A leachate low-dose effects by vom Saal and Hughes published in August 2005 seems to have found a suggestive correlation between the source of funding and the conclusion drawn. Industry-funded studies tend to find no significant effects whereas government-funded studies tend to find significant effects.[31]

Sodium hypochloritebleach and other alkali cleaners catalyze the release of the bisphenol A from polycarbonate containers.[32][33]Polycarbonate is incompatible with ammonia and acetone.Alcoholis a recommendedorganic solventfor cleaning grease and oils from polycarbonate.

Environmental impact

edit

Disposal

edit

Studies have shown that at temperatures above 70 °C, and high humidity, polycarbonate will hydrolyze tobisphenol A(BPA). After about 30 days at 85 °C/96% RH, surface crystals are formed which for 70% consisted of BPA.[34]BPA is a compound that is currently on the list of potential environmental hazardous chemicals. It is on the watch list of many countries, such as United States and Germany.[35]

-(-OC6H4)2C(CH3)2CO-)-n+ H2O → (CH3)2C(C6H4OH)2+ CO2

The leaching of BPA from polycarbonate can also occur at environmental temperature and normal pH (in landfills).The amount of leaching increases as the polycarbonate parts get older. A study found that the decomposition of BPA in landfills (under anaerobic conditions) will not occur.[35]It will therefore be persistent in landfills. Eventually, it will find its way into water bodies and contribute to aquatic pollution.[35][36]

Photo-oxidation of polycarbonate

edit

In the presence of UV light, oxidation of this polymer yields compounds such as ketones, phenols, o-phenoxybenzoic acid, benzyl alcohol and other unsaturated compounds. This has been suggested through kinetic and spectral studies. The yellow color formed after long exposure to sun can also be related to further oxidation of phenolic end group[37]

(OC6H4)2C(CH3)2CO )n+ O2,R* → (OC6H4)2C(CH3CH2)CO)n

This product can be further oxidized to form smaller unsaturated compounds. This can proceed via two different pathways, the products formed depends on which mechanism takes place.[38]

Pathway A

(OC6H4)2C(CH3CH2)CO + O2,H*HO(OC6H4)OCO + CH3COCH2(OC6H4)OCO

Pathway B

(OC6H4)2C(CH3CH2)CO)n+ O2,H*OCO(OC6H4)CH2OH + OCO(OC6H4)COCH3

Photo-aging reaction

edit

Photo-aging is another degradation route for polycarbonates. Polycarbonate molecules (such as the aromatic ring) absorb UV radiation. This absorbed energy causes cleavage of covalent bonds which initiates the photo-aging process. The reaction can be propagated via side chain oxidation, ring oxidation orphoto-Fries rearrangement.Products formed includephenyl salicylate,dihydroxybenzophenone groups, and hydroxydiphenyl ether groups.[37][39][40]

(C16H14O3)nC16H17O3+ C13H10O3

Thermal degradation

edit

Waste polycarbonate will degrade at high temperatures to form solid, liquid and gaseous pollutants. A study showed that the products were about 40–50 wt.% liquid, 14–16 wt.% gases, while 34–43 wt.% remained as solid residue. Liquid products contained mainly phenol derivatives (~75wt.%) and bisphenol (~10wt.%) also present.[39]Polycarbonate, however, can be safely used as a carbon source in the steel-making industry.[41]

Phenol derivatives are environmental pollutants, classified as volatile organic compounds (VOC). Studies show they are likely to facilitate ground level ozone formation and increase photo-chemical smog.[42]In aquatic bodies, they can potentially accumulate in organisms. They are persistent in landfills, do not readily evaporate and would remain in the atmosphere.[43]

Effect of fungi

edit

In 2001 a species of fungus inBelize,Geotrichum candidum,was found to consume the polycarbonate found incompact discs(CD).[44]This has prospects forbioremediation.However, this effect has not been reproduced.

See also

edit

References

edit
  1. ^"Lexan sheet technical manual"(PDF).SABIC.2009. Archived fromthe original(PDF)on 2015-03-16.Retrieved2015-07-18.
  2. ^Parvin, M. & Williams, J. G. (1975). "The effect of temperature on the fracture of polycarbonate".Journal of Materials Science.10(11): 1883.Bibcode:1975JMatS..10.1883P.doi:10.1007/BF00754478.S2CID135645940.
  3. ^Blumm, J.; Lindemann, A. (2003)."Characterization of the thermophysical properties of molten polymers and liquids using the flash technique"(PDF).High Temperatures – High Pressures.35/36 (6): 627.doi:10.1068/htjr144.
  4. ^CES Edupack 2010, Polycarbonate (PC) specs sheet
  5. ^Perez, Serge; Scaringe, Raymond P. (1987). "Crystalline features of 4,4'-isopropylidenediphenylbis(phenyl carbonate) and conformational analysis of the polycarbonate of 2,2-bis(4-hydroxyphenyl)propane".Macromolecules.20(1): 68–77.Bibcode:1987MaMol..20...68P.doi:10.1021/ma00167a014.
  6. ^abcdeVolker Serini "Polycarbonates" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2000.doi:10.1002/14356007.a21_207
  7. ^Djurner, K.; M??nson, J-A.; Rigdahl, M. (1978). "Crystallization of polycarbonate during injection molding at high pressures".Journal of Polymer Science: Polymer Letters Edition.16(8): 419–424.Bibcode:1978JPoSL..16..419D.doi:10.1002/pol.1978.130160806.ISSN0360-6384.
  8. ^Answers to Common Questions about Bayer Polycarbonate Resins.bayermaterialsciencenafta
  9. ^"Polycarbonate".city plastics. Archived fromthe originalon 2018-10-16.Retrieved2013-12-18.
  10. ^David W. Plester (1973)."The Effects of Radiation Sterilization on Plastics"(PDF).Sterilization Technology.p. 149.S2CID18798850.Archived fromthe original(PDF)on 2015-05-12.Polycarbonate can satisfactorily be given a single-dose sterilization exposure (22) but tends to become brittle much above 2.5 Mrad.
  11. ^"Film".execpc.Archived fromthe originalon 2023-03-09.Retrieved2012-07-19.
  12. ^"WIMA".wima.Archivedfrom the original on June 12, 2017.
  13. ^"Is this the end of owning music?".BBC News.3 January 2019.
  14. ^Egress technicians keep raptor pilots covered.Pacaf.af.mil. Retrieved on 2011-02-26.
  15. ^Emsley, John(9 November 2015).A Healthy, Wealthy, Sustainable World.Royal Society of Chemistry. p. 119.ISBN978-1-78262-589-6.Retrieved1 October2023.
  16. ^Alcohol restrictions for violent venues.State of New South Wales (Office of Liquor, Gaming & Racing)
  17. ^Ban on regular glass in licensed premises.The State of Queensland (Department of Justice and Attorney-General)
  18. ^"RDLohr's Clearly Superior Products"(PDF).wavelandps.Archived fromthe original(PDF)on 1 April 2010.
  19. ^Linda Jablanski (2015-03-31)."Which Plastic Material is Used in Lego Sets?".Archived from the original on 2017-03-05.{{cite web}}:CS1 maint: unfit URL (link)
  20. ^Powell, Douglas G. (September 1998)."Medical Applications of Polycarbonate".Medical Plastics and Biomaterials Magazine.Archived fromthe originalon 23 February 1999.
  21. ^"Dow Plastics Medical Application Policy".Plastics.dow.Archived fromthe originalon February 9, 2010.
  22. ^"Makrolon Polycarbonate Biocompatibility Grades".Archived fromthe originalon 2013-04-10.Retrieved2007-04-14.
  23. ^Chan, Julian M. W.; Ke, Xiyu; Sardon, Haritz; Engler, Amanda C.; Yang, Yi Yan; Hedrick, James L. (2014). "Chemically Modifiable N-Heterocycle-Functionalized Polycarbonates as a Platform for Diverse Smart Biomimetic Nanomaterials".Chemical Science.5(8): 3294–3300.doi:10.1039/C4SC00789A.
  24. ^ab "Build materials: metal vs glass vs plastic".Android Authority.19 July 2018.
  25. ^"Polycarbonate (PC)".ULProspector.Retrieved5 May2014.
  26. ^Philip Kotler; Waldemar Pfoertsch (17 May 2010).Ingredient Branding: Making the Invisible Visible.Springer Science & Business Media. pp. 205–.ISBN978-3-642-04214-0.
  27. ^"Polycarbonate is Polyfunctional".Chemical Institute of Canada. Archived fromthe originalon 5 May 2014.Retrieved5 May2014.
  28. ^Jerome T. Coe (27 August 2010)."Lexan Polycarbonate: 1953–1968".Unlikely Victory: How General Electric Succeeded in the Chemical Industry.John Wiley & Sons. pp. 71–77.ISBN978-0-470-93547-7.
  29. ^"General Electric to Sell Plastics Division".NY Times. 2007-05-22.Retrieved2020-07-21.
  30. ^Howdeshell, KL; Peterman PH; Judy BM; Taylor JA; Orazio CE; Ruhlen RL; Vom Saal FS; Welshons WV (2003)."Bisphenol A is released from used polycarbonate animal cages into water at room temperature".Environmental Health Perspectives.111(9): 1180–7.Bibcode:2003EnvHP.111.1180H.doi:10.1289/ehp.5993.PMC1241572.PMID12842771.
  31. ^vom Saal FS, Hughes C (2005)."An extensive new literature concerning low-dose effects of bisphenol A shows the need for a new risk assessment".Environ. Health Perspect.113(8): 926–33.doi:10.1289/ehp.7713.PMC1280330.PMID16079060.
  32. ^Hunt, PA; Kara E. Koehler; Martha Susiarjo; Craig A. Hodges; Arlene Ilagan; Robert C. Voigt; Sally Thomas; Brian F. Thomas; Terry J. Hassold (2003)."Bisphenol A Exposure Causes Meiotic Aneuploidy in the Female Mouse".Current Biology.13(7): 546–553.Bibcode:2003CBio...13..546H.doi:10.1016/S0960-9822(03)00189-1.PMID12676084.S2CID10168552.
  33. ^Koehler, KE; Robert C. Voigt; Sally Thomas; Bruce Lamb; Cheryl Urban; Terry Hassold; Patricia A. Hunt (2003)."When disaster strikes: rethinking caging materials".Lab Animal.32(4): 24–27.doi:10.1038/laban0403-24.PMID19753748.S2CID37343342.Archived fromthe originalon 2009-07-06.Retrieved2008-05-06.
  34. ^Bair, H. E.; Falcone, D. R.; Hellman, M. Y.; Johnson, G. E.; Kelleher, P. G. (1981-06-01). "Hydrolysis of polycarbonate to yield BPA".Journal of Applied Polymer Science.26(6): 1777.doi:10.1002/app.1981.070260603.
  35. ^abcMorin, Nicolas; Arp, Hans Peter H.; Hale, Sarah E. (July 2015). "Bisphenol A in Solid Waste Materials, Leachate Water, and Air Particles from Norwegian Waste-Handling Facilities: Presence and Partitioning Behavior".Environmental Science & Technology.49(13): 7675–7683.Bibcode:2015EnST...49.7675M.doi:10.1021/acs.est.5b01307.PMID26055751.
  36. ^Chin, Yu-Ping; Miller, Penney L.; Zeng, Lingke; Cawley, Kaelin; Weavers, Linda K. (November 2004). "Photosensitized Degradation of Bisphenol A by Dissolved Organic Matter †".Environmental Science & Technology.38(22): 5888–5894.Bibcode:2004EnST...38.5888C.doi:10.1021/es0496569.PMID15573586.
  37. ^abChow, Jimmy T. (2007-08-06).Environmental assessment for bisphenol-a and polycarbonate(Master thesis). Kansas State University.hdl:2097/368.
  38. ^Carroccio, Sabrina; Puglisi, Concetto; Montaudo, Giorgio (2002). "Mechanisms of Thermal Oxidation of Poly(bisphenol A carbonate)".Macromolecules.35(11): 4297–4305.Bibcode:2002MaMol..35.4297C.doi:10.1021/ma012077t.
  39. ^abCollin, S.; Bussière, P. -O.; Thérias, S.; Lambert, J. -M.; Perdereau, J.; Gardette, J. -L. (2012-11-01). "Physicochemical and mechanical impacts of photo-ageing on bisphenol a polycarbonate".Polymer Degradation and Stability.97(11): 2284–2293.doi:10.1016/j.polymdegradstab.2012.07.036.
  40. ^Tjandraatmadja, G. F.; Burn, L. S.; Jollands, M. J. (1999)."The effects of ultraviolet radiation on polycarbonate glazing"(PDF).
  41. ^Assadi, M. Hussein N.; Sahajwalla, V. (2014). "Recycling End-of-Life Polycarbonate in Steelmaking: Ab Initio Study of Carbon Dissolution in Molten Iron".Ind. Eng. Chem. Res.53(10): 3861–3864.arXiv:2204.08706.doi:10.1021/ie4031105.S2CID101308914.
  42. ^"Pollution Database".pollution.unibuc.ro.Archived fromthe originalon 2017-12-29.Retrieved2016-11-14.
  43. ^"Pollutant Fact Sheet".apps.sepa.org.uk.Archived fromthe originalon 2017-01-09.Retrieved2016-11-14.
  44. ^Bosch, Xavier (2001-06-27)."Fungus eats CD".Nature News.doi:10.1038/news010628-11.
edit