Poly(methyl methacrylate)

Last updated
Poly(methyl methacrylate)
PMMA repeating unit.svg
Names
IUPAC name
Poly(methyl 2-methylpropenoate)
Other names
  • Poly(methyl methacrylate)
  • PMMA
  • Methyl methacrylate resin
  • Perspex
Identifiers
3D model (JSmol)
ChemSpider
  • None
ECHA InfoCard 100.112.313 OOjs UI icon edit-ltr-progressive.svg
KEGG
UNII
  • CCC(C)(C(=O)OC)CC(C)(C(=O)OC)CC(C)(C(=O)OC)CC(C)(C(=O)OC)CC(C)(C(=O)OC)C
Properties
(C 5 H 8 O 2)n
Molar mass Varies
Density 1.18 g/cm3 [1]
−9.06×10−6 (SI, 22 °C) [2]
1.4905 at 589.3 nm [3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Lichtenberg figure: high-voltage dielectric breakdown in an acrylic polymer block Lichtenberg figure in block of Plexiglas.jpg
Lichtenberg figure: high-voltage dielectric breakdown in an acrylic polymer block

Poly(methyl methacrylate) (PMMA) is the synthetic polymer derived from methyl methacrylate. It is used as an engineering plastic, and it is a transparent thermoplastic. PMMA is also known as acrylic, acrylic glass, as well as by the trade names and brands Crylux, Hesalite, Plexiglas, Acrylite, Lucite, and Perspex, among several others (see below). This plastic is often used in sheet form as a lightweight or shatter-resistant alternative to glass. It can also be used as a casting resin, in inks and coatings, and for many other purposes.

Contents

It is often technically classified as a type of glass, in that it is a non-crystalline vitreous substance—hence its occasional historic designation as acrylic glass.

History

The first acrylic acid was created in 1843. Methacrylic acid, derived from acrylic acid, was formulated in 1865. The reaction between methacrylic acid and methanol results in the ester methyl methacrylate.

It was developed in 1928 in several different laboratories by many chemists, such as William R. Conn, Otto Röhm, and Walter Bauer, and first brought to market in 1933 by German Röhm & Haas AG (as of January 2019, part of Evonik Industries) and its partner and former U.S. affiliate Rohm and Haas Company under the trademark Plexiglas. [4]

Polymethyl methacrylate was discovered in the early 1930s by British chemists Rowland Hill and John Crawford at Imperial Chemical Industries (ICI) in the United Kingdom.[ citation needed ] ICI registered the product under the trademark Perspex. About the same time, chemist and industrialist Otto Röhm of Röhm and Haas AG in Germany attempted to produce safety glass by polymerizing methyl methacrylate between two layers of glass. The polymer separated from the glass as a clear plastic sheet, which Röhm gave the trademarked name Plexiglas in 1933. [5] Both Perspex and Plexiglas were commercialized in the late 1930s. In the United States, E.I. du Pont de Nemours & Company (now DuPont Company) subsequently introduced its own product under the trademark Lucite. In 1936 ICI Acrylics (now Lucite International) began the first commercially viable production of acrylic safety glass. During World War II both Allied and Axis forces used acrylic glass for submarine periscopes and aircraft windscreen, canopies, and gun turrets. Scraps of acrylic were also used to made clear pistol grips for the M1911A1 pistol or clear handle grips for the M1 bayonet or theater knifes so that soldiers could put small photos of loved ones or pin-up girls' pictures inside. They were called "Sweetheart Grips" or "Pin-up Grips". Others were used to make handles for theater knives made from scrap materials and people who made them got artistic or creative. [6] Civilian applications followed after the war. [7]

Names

Common orthographic stylings include polymethyl methacrylate [8] [9] and polymethylmethacrylate. The full IUPAC chemical name is poly(methyl 2-methylpropenoate). (It is a common mistake to use "an" instead of "en".)

Although PMMA is often called simply "acrylic", acrylic can also refer to other polymers or copolymers containing polyacrylonitrile. Notable trade names and brands include Acrylite, Altuglas, [10] Astariglas, Cho Chen, Crystallite, Cyrolite, [11] Hesalite (when used in Omega watches), Lucite, [12] Optix, [11] Oroglas, [13] PerClax, Perspex, [11] Plexiglas, [11] [14] R-Cast, and Sumipex.

PMMA is an economical alternative to polycarbonate (PC) when tensile strength, flexural strength, transparency, polishability, and UV tolerance are more important than impact strength, chemical resistance, and heat resistance. Additionally, PMMA does not contain the potentially harmful bisphenol-A subunits found in polycarbonate and is a far better choice for laser cutting. [15] It is often preferred because of its moderate properties, easy handling and processing, and low cost. Non-modified PMMA behaves in a brittle manner when under load, especially under an impact force, and is more prone to scratching than conventional inorganic glass, but modified PMMA is sometimes able to achieve high scratch and impact resistance.

Properties

Skeletal structure of methyl methacrylate, the constituent monomer of PMMA Methyl-methacrylate-skeletal.png
Skeletal structure of methyl methacrylate, the constituent monomer of PMMA
Pieces of Plexiglas taken from the windscreen of a German plane shot down during World War II Perspex pieces (AM 2007.10.2-2).jpg
Pieces of Plexiglas taken from the windscreen of a German plane shot down during World War II

PMMA is a strong, tough, and lightweight material. It has a density of 1.17–1.20 g/cm3, [1] [16] which is less than half that of glass. [1] It also has good impact strength, higher than both glass and polystyrene, but significantly lower than polycarbonate and some engineered polymers. PMMA ignites at 460 °C (860 °F) and burns, forming carbon dioxide, water, carbon monoxide, and low-molecular-weight compounds, including formaldehyde. [17]

PMMA transmits up to 92% of visible light (3 mm (0.12 in) thickness), [18] and gives a reflection of about 4% from each of its surfaces due to its refractive index (1.4905 at 589.3 nm). [3] It filters ultraviolet (UV) light at wavelengths below about 300 nm (similar to ordinary window glass). Some manufacturers [19] add coatings or additives to PMMA to improve absorption in the 300–400 nm range. PMMA passes infrared light of up to 2,800 nm and blocks IR of longer wavelengths up to 25,000 nm. Colored PMMA varieties allow specific IR wavelengths to pass while blocking visible light (for remote control or heat sensor applications, for example).

PMMA swells and dissolves in many organic solvents; it also has poor resistance to many other chemicals due to its easily hydrolyzed ester groups. Nevertheless, its environmental stability is superior to most other plastics such as polystyrene and polyethylene, and therefore it is often the material of choice for outdoor applications. [20]

PMMA has a maximum water absorption ratio of 0.3–0.4% by weight. [16] Tensile strength decreases with increased water absorption. [21] Its coefficient of thermal expansion is relatively high at (5–10)×10−5 °C−1. [22]

The Futuro house was made of fibreglass-reinforced polyester plastic, polyester-polyurethane, and poly(methylmethacrylate); one of them was found to be degrading by cyanobacteria and Archaea. [23] [24]

PMMA can be joined using cyanoacrylate cement (commonly known as superglue), with heat (welding), or by using chlorinated solvents such as dichloromethane or trichloromethane [25] (chloroform) to dissolve the plastic at the joint, which then fuses and sets, forming an almost invisible weld. Scratches may easily be removed by polishing or by heating the surface of the material. Laser cutting may be used to form intricate designs from PMMA sheets. PMMA vaporizes to gaseous compounds (including its monomers) upon laser cutting, so a very clean cut is made, and cutting is performed very easily. However, the pulsed lasercutting introduces high internal stresses, which on exposure to solvents produce undesirable "stress-crazing" at the cut edge and several millimetres deep. Even ammonium-based glass-cleaner and almost everything short of soap-and-water produces similar undesirable crazing, sometimes over the entire surface of the cut parts, at great distances from the stressed edge. [26] Annealing the PMMA sheet/parts is therefore an obligatory post-processing step when intending to chemically bond lasercut parts together.

In the majority of applications, PMMA will not shatter. Rather, it breaks into large dull pieces. Since PMMA is softer and more easily scratched than glass, scratch-resistant coatings are often added to PMMA sheets to protect it (as well as possible other functions).

Pure poly(methyl methacrylate) homopolymer is rarely sold as an end product, since it is not optimized for most applications. Rather, modified formulations with varying amounts of other comonomers, additives, and fillers are created for uses where specific properties are required. For example:

Synthesis and processing

PMMA is routinely produced by emulsion polymerization, solution polymerization, and bulk polymerization. Generally, radical initiation is used (including living polymerization methods), but anionic polymerization of PMMA can also be performed. [28]

The glass transition temperature (Tg) of atactic PMMA is 105 °C (221 °F). The Tg values of commercial grades of PMMA range from 85 to 165 °C (185 to 329 °F); the range is so wide because of the vast number of commercial compositions that are copolymers with co-monomers other than methyl methacrylate. PMMA is thus an organic glass at room temperature; i.e., it is below its Tg. The forming temperature starts at the glass transition temperature and goes up from there. [29] All common molding processes may be used, including injection molding, compression molding, and extrusion. The highest quality PMMA sheets are produced by cell casting, but in this case, the polymerization and molding steps occur concurrently. The strength of the material is higher than molding grades owing to its extremely high molecular mass. Rubber toughening has been used to increase the toughness of PMMA to overcome its brittle behavior in response to applied loads.

Applications

Close-up of pressure sphere of the bathyscaphe Trieste, with a single conical window of PMMA set into sphere hull. The very small black circle (smaller than the man's head) is the inner side of the plastic "window", only a few inches in diameter. The larger circular clear black area represents the larger outer side of the thick one-piece plastic cone "window". Bathyscaphe Trieste sphere.jpg
Close-up of pressure sphere of the bathyscaphe Trieste, with a single conical window of PMMA set into sphere hull. The very small black circle (smaller than the man's head) is the inner side of the plastic "window", only a few inches in diameter. The larger circular clear black area represents the larger outer side of the thick one-piece plastic cone "window".

Being transparent and durable, PMMA is a versatile material and has been used in a wide range of fields and applications such as rear-lights and instrument clusters for vehicles, appliances, and lenses for glasses. PMMA in the form of sheets affords to shatter resistant panels for building windows, skylights, bulletproof security barriers, signs and displays, sanitary ware (bathtubs), LCD screens, furniture and many other applications. It is also used for coating polymers based on MMA provides outstanding stability against environmental conditions with reduced emission of VOC. Methacrylate polymers are used extensively in medical and dental applications where purity and stability are critical to performance. [28]

Glass substitute

10-meter (33 ft) deep Monterey Bay Aquarium tank has acrylic windows up to 33 centimeters (13 in) thick to withstand the water pressure. KelpAquarium.jpg
10-meter (33 ft) deep Monterey Bay Aquarium tank has acrylic windows up to 33 centimeters (13 in) thick to withstand the water pressure.

Daylight redirection

Medicine

In particular, acrylic-type lenses are useful for cataract surgery in patients that have recurrent ocular inflammation (uveitis), as acrylic material induces less inflammation.

Dentistry

Due to its aforementioned biocompatibility, poly(methyl methacrylate) is a commonly used material in modern dentistry, particularly in the fabrication of dental prosthetics, artificial teeth, and orthodontic appliances.

Art and aesthetics

Lexus Perspex car sculpture Lexus LF-A Crystallised Wind.jpg
Lexus Perspex car sculpture
PMMA art by Manfred Kielnhofer Maylan-interior-design-neue-wiener-werkstaette-interlux-roehm- evonik- indeustries-contemporary-light-art-sedan-chair-seats-manfred-kielnhofer-illumination-auchtion.jpg
PMMA art by Manfred Kielnhofer
Kawai acrylic grand piano Kawai CR-40A.jpg
Kawai acrylic grand piano
Lucite Bangle Bracelet "Rootbeer" Lucite Bangle Bracelet - DPLA - 72b817c152132c7bf0d40c71240c4f1e.jpg
Lucite Bangle Bracelet
Illustrative and secure bromine chemical sample used for teaching. The glass sample vial of the corrosive and poisonous liquid has been cast into an acrylic plastic cube Bromine vial in acrylic cube.jpg
Illustrative and secure bromine chemical sample used for teaching. The glass sample vial of the corrosive and poisonous liquid has been cast into an acrylic plastic cube

Methyl methacrylate "synthetic resin" for casting (simply the bulk liquid chemical) may be used in conjunction with a polymerization catalyst such as methyl ethyl ketone peroxide (MEKP), to produce hardened transparent PMMA in any shape, from a mold. Objects like insects or coins, or even dangerous chemicals in breakable quartz ampules, may be embedded in such "cast" blocks, for display and safe handling.

Other uses

High-heel shoes made of Lucite Acrylic Heels.jpg
High-heel shoes made of Lucite
An electric bass guitar made from poly(methyl methacrylate) Basscat Bass.jpg
An electric bass guitar made from poly(methyl methacrylate)
A Futuro house in Warrington, New Zealand Futuro house Warrington.JPG
A Futuro house in Warrington, New Zealand

See also

Related Research Articles

<span class="mw-page-title-main">Petrochemical</span> Chemical product derived from petroleum

Petrochemicals are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sources such as maize, palm fruit or sugar cane.

<span class="mw-page-title-main">Thermoplastic</span> Plastic that softens with heat and hardens on cooling

A thermoplastic, or thermosoftening plastic, is any plastic polymer material that becomes pliable or moldable at a certain elevated temperature and solidifies upon cooling.

Acrylates are the salts, esters, and conjugate bases of acrylic acid. The acrylate ion is the anion CH2=CHCO−2. Often, acrylate refers to esters of acrylic acid, the most common member being methyl acrylate. These acrylates contain vinyl groups. These compounds are of interest because they are bifunctional: the vinyl group is susceptible to polymerization and the carboxylate group carries myriad functionalities.

<span class="mw-page-title-main">Polycarbonate</span> Family of polymers

Polycarbonates (PC) are a group of thermoplastic polymers containing carbonate groups in their chemical structures. Polycarbonates used in engineering are strong, tough materials, and some grades are optically transparent. They are easily worked, molded, and thermoformed. Because of these properties, polycarbonates find many applications. Polycarbonates do not have a unique resin identification code (RIC) and are identified as "Other", 7 on the RIC list. Products made from polycarbonate can contain the precursor monomer bisphenol A (BPA).

<span class="mw-page-title-main">Methyl methacrylate</span> Chemical compound

Methyl methacrylate (MMA) is an organic compound with the formula CH2=C(CH3)COOCH3. This colorless liquid, the methyl ester of methacrylic acid (MAA), is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA).

<span class="mw-page-title-main">Engineering plastic</span> Plastics often used for making mechanical parts

Engineering plastics are a group of plastic materials that have better mechanical or thermal properties than the more widely used commodity plastics.

<span class="mw-page-title-main">CR-39</span> Plastic

Poly(allyl diglycol carbonate) (PADC) is a plastic commonly used in the manufacture of eyeglass lenses alongside the material PMMA (polymethyl methacrylate). The monomer is allyl diglycol carbonate (ADC). The term CR-39 technically refers to the ADC monomer, but is more commonly used to refer to the finished plastic.

<span class="mw-page-title-main">Poly(methyl acrylate)</span> Chemical compound

Poly(methyl acrylate) (PMA) is a family of organic polymers with the formula (CH2CHCO2CH3)n. It is a synthetic acrylate polymer derived from methyl acrylate monomer. The polymers are colorless. This homopolymer is far less important than copolymers derived from methyl acrylate and other monomers. PMA is softer than polymethyl methacrylate (PMMA), It is tough, leathery, and flexible.

<span class="mw-page-title-main">Acrylate polymer</span> Group of polymers prepared from acrylate monomers

An acrylate polymer is any of a group of polymers prepared from acrylate monomers. These plastics are noted for their transparency, resistance to breakage, and elasticity.

Otto Karl Julius Röhm was one of the founders and a longtime president of the Röhm und Haas chemical company which became later in the USA the Rohm and Haas and in Germany the Röhm GmbH.

Synthetic resins are industrially produced resins, typically viscous substances that convert into rigid polymers by the process of curing. In order to undergo curing, resins typically contain reactive end groups, such as acrylates or epoxides. Some synthetic resins have properties similar to natural plant resins, but many do not.

Bone cements have been used very successfully to anchor artificial joints for more than half a century. Artificial joints are anchored with bone cement. The bone cement fills the free space between the prosthesis and the bone and plays the important role of an elastic zone. This is necessary because the human hip is acted on by approximately 10–12 times the body weight and therefore the bone cement must absorb the forces acting on the hips to ensure that the artificial implant remains in place over the long term.

Acetone cyanohydrin (ACH) is an organic compound used in the production of methyl methacrylate, the monomer of the transparent plastic polymethyl methacrylate (PMMA), also known as acrylic. It liberates hydrogen cyanide easily, so it is used as a source of such. For this reason, this cyanohydrin is also highly toxic.

In materials science, a polymer blend, or polymer mixture, is a member of a class of materials analogous to metal alloys, in which at least two polymers are blended together to create a new material with different physical properties.

<span class="mw-page-title-main">Artificial nails</span> Beauty accessories

Artificial nails, also known as fake nails, false nails, acrylic nails, nail extensions or nail enhancements, are extensions placed over fingernails as fashion accessories. Many artificial nail designs attempt to mimic the appearance of real fingernails as closely as possible, while others may deliberately stray in favor of an artistic look.

Resin casting is a method of plastic casting where a mold is filled with a liquid synthetic resin, which then hardens. It is primarily used for small-scale production like industrial prototypes and dentistry. It can be done by amateur hobbyists with little initial investment, and is used in the production of collectible toys, models and figures, as well as small-scale jewellery production.

Cell casting is a method used for creating poly(methyl methacrylate) (PMMA) sheets. Liquid monomer is poured between two flat sheets of toughened glass sealed with a rubber gasket and heated for polymerization. Because the glass sheets may contain surface scratches or sag during the process, this traditional method has some disadvantages: among other problems, the PMMA sheets may contain variations in thickness and surface defects. For many applications it has since been replaced by other methods for making PMMA such as extrusion, which gives uniform surface features. However, for applications where strength is critical cell casting techniques are still employed in conjunction with stretching, which produces a stronger overall material.

<span class="mw-page-title-main">Cast acrylic</span>

Cast Acrylic is a form of poly(methyl methacrylate) (PMMA). It is formed by casting the monomer, methyl methacrylate, mixed with initiators and possibly other additives into a form or mold. Sheet and rod stock are generated by casting into static forms, while tubing is done in rotational molds.

<span class="mw-page-title-main">Transparent wood composite</span>

Transparent wood composites are novel wood materials which have up to 90% transparency. Some have better mechanical properties than wood itself. They were made for the first time in 1992. These materials are significantly more biodegradable than glass and plastics. Transparent wood is also shatterproof, making it suitable for applications like cell phone screens.

<span class="mw-page-title-main">Röhm GmbH (Darmstadt)</span> German chemicals company

Röhm GmbH is a German chemicals company headquartered Darmstadt, Germany. Röhm employs around 3,500 employees at 13 sites in Germany, China, USA and South-Africa. In 2021, the company generated revenues of €1.8 billion. Röhm GmbH was founded through the carve-out of the Methacrylates Verbund and CyPlus GmbH from Evonik Industries.

References

  1. 1 2 3 Polymethylmethacrylate (PMMA, Acrylic) Archived 2015-04-02 at the Wayback Machine . Makeitfrom.com. Retrieved 2015-03-23.
  2. Wapler, M. C.; Leupold, J.; Dragonu, I.; von Elverfeldt, D.; Zaitsev, M.; Wallrabe, U. (2014). "Magnetic properties of materials for MR engineering, micro-MR and beyond". JMR. 242 (2014): 233–242. arXiv: 1403.4760 . Bibcode:2014JMagR.242..233W. doi:10.1016/j.jmr.2014.02.005. PMID   24705364. S2CID   11545416.
  3. 1 2 Refractive index and related constants – Poly(methyl methacrylate) (PMMA, Acrylic glass) Archived 2014-11-06 at the Wayback Machine . Refractiveindex.info. Retrieved 2014-10-27.
  4. Plexiglas history by Evonik (in German).
  5. "DPMAregister | Marken - Registerauskunft". register.dpma.de. Retrieved 2021-09-29.
  6. Congressional Record: Proceedings and Debates of the 77th Congress First Session (Volume 87, Part 11 ed.). Washington, D.C.: U.S. Government Printing Office. 1941. pp. A2300–A2302. Retrieved 3 August 2020.
  7. "Polymethyl methacrylate | chemical compound". Archived from the original on 2017-10-31. Retrieved 2017-05-22.
  8. "polymethyl methacrylate" , Dorland's Illustrated Medical Dictionary, Elsevier
  9. "polymethyl methacrylate". Merriam-Webster.com Dictionary . Merriam-Webster.
  10. David K. Platt (1 January 2003). Engineering and High Performance Plastics Market Report: A Rapra Market Report. Smithers Rapra. p. 170. ISBN   978-1-85957-380-8. Archived from the original on 21 April 2016.
  11. 1 2 3 4 Charles A. Harper; Edward M. Petrie (10 October 2003). Plastics Materials and Processes: A Concise Encyclopedia. John Wiley & Sons. p. 9. ISBN   978-0-471-45920-0. Archived from the original on 20 April 2016.
  12. "Trademark Electronic Search System". TESS. US Patent and Trademark Office. p. Search for Registration Number 0350093. Retrieved 29 June 2014.
  13. "Misused materials stoked Sumerland fire". New Scientist. 62 (902). IPC Magazines: 684. 13 June 1974. ISSN   0262-4079. Archived from the original on 21 April 2016.
  14. "WIPO Global Brand Database". Archived from the original on 2013-01-21. Retrieved 2013-01-25.
  15. "Never cut these materials" (PDF).[ failed verification ]
  16. 1 2 DATA TABLE FOR: Polymers: Commodity Polymers: PMMA Archived 2007-12-13 at the Wayback Machine . Matbase.com. Retrieved 2012-05-09.
  17. Zeng, W. R.; Li, S. F.; Chow, W. K. (2002). "Preliminary Studies on Burning Behavior of Polymethylmethacrylate (PMMA)". Journal of Fire Sciences. 20 (4): 297–317. doi:10.1177/073490402762574749. hdl: 10397/31946 . S2CID   97589855. INIST   14365060.
  18. McKeen, Laurence W. (2019). The effect of UV light and weather on plastics and elastomers (4th ed.). Washington, WA: Elsevier. p. 254. ISBN   978-0-1281-6457-0.
  19. Altuglas International Plexiglas UF-3 UF-4 and UF-5 sheets Archived 2006-11-17 at the Wayback Machine . Plexiglas.com. Retrieved 2012-05-09.
  20. Myer Ezrin Plastics Failure Guide: Cause and Prevention Archived 2016-04-21 at the Wayback Machine , Hanser Verlag, 1996 ISBN   1-56990-184-8, p. 168
  21. Ishiyama, Chiemi; Yamamoto, Yoshito; Higo, Yakichi (2005). Buchheit, T.; Minor, A.; Spolenak, R.; et al. (eds.). "Effects of Humidity History on the Tensile Deformation Behaviour of Poly(methyl–methacrylate) (PMMA) Films". MRS Proceedings. 875: O12.7. doi:10.1557/PROC-875-O12.7.
  22. "Tangram Technology Ltd. – Polymer Data File – PMMA". Archived from the original on 2010-04-21.
  23. Cappitelli, Francesca; Principi, Pamela; Sorlini, Claudia (2006). "Biodeterioration of modern materials in contemporary collections: Can biotechnology help?". Trends in Biotechnology. 24 (8): 350–4. doi:10.1016/j.tibtech.2006.06.001. PMID   16782219.
  24. Rinaldi, Andrea (2006). "Saving a fragile legacy. Biotechnology and microbiology are increasingly used to preserve and restore the world's cultural heritage". EMBO Reports. 7 (11): 1075–9. doi:10.1038/sj.embor.7400844. PMC   1679785 . PMID   17077862.
  25. "Working with Plexiglas" Archived 2015-02-21 at the Wayback Machine . science-projects.com.
  26. Andersen, Hans J. "Tensions in acrylics when laser cutting". Archived from the original on 8 December 2015. Retrieved 23 December 2014.
  27. López, Alejandro; Hoess, Andreas; Thersleff, Thomas; Ott, Marjam; Engqvist, Håkan; Persson, Cecilia (2011-01-01). "Low-modulus PMMA bone cement modified with castor oil". Bio-Medical Materials and Engineering. 21 (5–6): 323–332. doi: 10.3233/BME-2012-0679 . ISSN   0959-2989. PMID   22561251.
  28. 1 2 Stickler, Manfred; Rhein, Thoma (2000). "Polymethacrylates". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a21_473. ISBN   3527306730.
  29. Ashby, Michael F. (2005). Materials Selection in Mechanical Design (3rd ed.). Elsevier. p.  519. ISBN   978-0-7506-6168-3.
  30. Kutz, Myer (2002). Handbook of Materials Selection . John Wiley & Sons. p.  341. ISBN   978-0-471-35924-1.
  31. Terry Pepper, Seeing the Light, Illumination Archived 2009-01-23 at the Wayback Machine . Terrypepper.com. Retrieved 2012-05-09.
  32. Deplazes, Andrea, ed. (2013). Constructing Architecture – Materials Processes Structures, A Handbook. Birkhäuser. ISBN   978-3038214526.
  33. Yeang, Ken. Light Pipes: An Innovative Design Device for Bringing Natural Daylight and Illumination into Buildings with Deep Floor Plan Archived 2009-03-05 at the Wayback Machine , Nomination for the Far East Economic Review Asian Innovation Awards 2003
  34. "Lighting up your workplace". Fresh Innovators. May 9, 2005. Archived from the original on 2 July 2005.
  35. Kenneth Yeang Archived 2008-09-25 at the Wayback Machine , World Cities Summit 2008, June 23–25, 2008, Singapore
  36. Gerchikov, Victor; Mossman, Michele; Whitehead, Lorne (2005). "Modeling Attenuation versus Length in Practical Light Guides". LEUKOS. 1 (4): 47–59. doi:10.1582/LEUKOS.01.04.003. S2CID   220306943.
  37. How Serraglaze works Archived 2009-03-05 at the Wayback Machine . Bendinglight.co.uk. Retrieved 2012-05-09.
  38. Glaze of light Archived 2009-01-10 at the Wayback Machine , Building Design Online, June 8, 2007
  39. Robert A. Meyers, "Molecular biology and biotechnology: a comprehensive desk reference", Wiley-VCH, 1995, p. 722 ISBN   1-56081-925-1
  40. Apple, David J (2006). Sir Harold Ridely and His Fight for Sight: He Changed the World So That We May Better See It. Thorofare NJ USA: Slack. ISBN   978-1-55642-786-2.
  41. Carroll, Gregory T.; Kirschman, David L. (2022-07-13). "A portable negative pressure unit reduces bone cement fumes in a simulated operating room". Scientific Reports. 12 (1): 11890. Bibcode:2022NatSR..1211890C. doi:10.1038/s41598-022-16227-x. ISSN   2045-2322. PMC   9279392 . PMID   35831355.
  42. Kaufmann, Timothy J.; Jensen, Mary E.; Ford, Gabriele; Gill, Lena L.; Marx, William F.; Kallmes, David F. (2002-04-01). "Cardiovascular Effects of Polymethylmethacrylate Use in Percutaneous Vertebroplasty". American Journal of Neuroradiology. 23 (4): 601–4. PMC   7975098 . PMID   11950651.
  43. "Filling in Wrinkles Safely". U.S. Food and Drug Administration. February 28, 2015. Archived from the original on 21 November 2015. Retrieved 8 December 2015.
  44. Zarb, George Albert (2013). Prosthodontic treatment for edentulous patients: complete dentures and implant-supported prostheses (13th ed.). St. Louis, Mo.: Elsevier Mosby. ISBN   9780323078443. OCLC   773020864.
  45. de Swart, Ursula. My Life with Jan. Collection of Jock de Swart, Durango, CO
  46. Syurik, Julia; Jacucci, Gianni; Onelli, Olimpia D.; Holscher, Hendrik; Vignolini, Silvia (22 February 2018). "Bio-inspired Highly Scattering Networks via Polymer Phase Separation". Advanced Functional Materials. 28 (24): 1706901. doi: 10.1002/adfm.201706901 .
  47. Goodman, Robert L. (2002-11-19). How Electronic Things Work... And What to do When They Don't . McGraw Hill Professional. ISBN   9780071429245. PMMA Laserdisc.
  48. Williams, K.S.; Mcdonnell, T. (2012), "Recycling liquid crystal displays", Waste Electrical and Electronic Equipment (WEEE) Handbook, Elsevier, pp. 312–338, doi:10.1533/9780857096333.3.312, ISBN   978-0-85709-089-8 , retrieved 2022-06-27
  49. Duarte, F. J. (Ed.), Tunable Laser Applications (CRC, New York, 2009) Chapters 3 and 4.
  50. 1 2 Lapshin, R. V.; Alekhin, A. P.; Kirilenko, A. G.; Odintsov, S. L.; Krotkov, V. A. (2010). "Vacuum ultraviolet smoothing of nanometer-scale asperities of poly(methyl methacrylate) surface". Journal of Surface Investigation. X-ray, Synchrotron and Neutron Techniques. 4 (1): 1–11. doi:10.1134/S1027451010010015. S2CID   97385151.
  51. Bedocs, Paul M.; Cliffel, Maureen; Mahon, Michael J.; Pui, John (March 2008). "Invisible tattoo granuloma". Cutis. 81 (3): 262–264. ISSN   0011-4162. PMID   18441850.
  52. JS2K-PLT Archived 2007-09-28 at the Wayback Machine . Ibanezregister.com. Retrieved 2012-05-09.
  53. Symington, Jan (2006). "Salon management". Australian nail technology. Croydon, Victoria, Australia: Tertiary Press. p. 11. ISBN   978-0864585981.