Names | |
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IUPAC name Poly(methyl 2-methylpropenoate) | |
Other names
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Identifiers | |
3D model (JSmol) | |
ChemSpider |
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ECHA InfoCard | 100.112.313 |
KEGG | |
UNII | |
CompTox Dashboard (EPA) | |
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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] | |
Refractive index (nD) | 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). |
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.
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.
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 [4] 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. [5]
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. [6] 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. [7] Civilian applications followed after the war. [8]
Common orthographic stylings include polymethyl methacrylate [9] [10] 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, [11] Altuglas, [12] Astariglas, [13] Cho Chen, [14] Crystallite, Cyrolite, [15] Hesalite (when used in Omega watches), Lucite, [16] Optix, [15] Oroglas, [17] PerClax, Perspex, [15] Plexiglas, [15] [18] R-Cast, [19] 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. [20] Additionally, PMMA does not contain the potentially harmful bisphenol-A subunits found in polycarbonate and is a far better choice for laser cutting. [21] 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.
PMMA is a strong, tough, and lightweight material. It has a density of 1.17–1.20 g/cm3, [1] [22] 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. [23]
PMMA transmits up to 92% of visible light (3 mm thickness), 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 [24] 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. [25]
PMMA has a maximum water absorption ratio of 0.3–0.4% by weight. [22] Tensile strength decreases with increased water absorption. [26] Its coefficient of thermal expansion is relatively high at (5–10)×10−5 °C−1. [27]
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. [28] [29]
PMMA can be joined using cyanoacrylate cement (commonly known as superglue), with heat (welding), or by using chlorinated solvents such as dichloromethane or trichloromethane [30] (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. [31] 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, it 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,
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. [33]
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. [34] 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.
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 & 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. [33]
In particular, acrylic-type lenses are useful for cataract surgery in patients that have recurrent ocular inflammation (uveitis), as acrylic material induces less inflammation.
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.
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.
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.
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.
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).
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).
Engineering plastics are a group of plastic materials that have better mechanical or thermal properties than the more widely used commodity plastics.
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.
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.
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.
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.
Rubber toughening is a process in which rubber nanoparticles are interspersed within a polymer matrix to increase the mechanical robustness, or toughness, of the material. By "toughening" a polymer it is meant that the ability of the polymeric substance to absorb energy and plastically deform without fracture is increased. Considering the significant advantages in mechanical properties that rubber toughening offers, most major thermoplastics are available in rubber-toughened versions; for many engineering applications, material toughness is a deciding factor in final material selection.
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.
Twin-wall plastic, specifically twin-wall polycarbonate, is an extruded multi-wall polymer product created for applications where its strength, thermally insulative properties, and moderate cost are ideal. Polycarbonate, which is most commonly formed through the reaction of Bisphenol A and Carbonyl Chloride, is an extremely versatile material. It is significantly lighter than glass, while managing to be stronger, more flexible, and more impact resistant. Twin-wall polycarbonate is used most commonly for green houses, where it can support itself in a structurally sound configuration, limit the amount of UV light due to its nominal translucence, and can withstand the rigors of daily abuse in an outdoor environment. The stagnant air in the cellular space between sheets provides insulation, and additional cell layers can be extruded to enhance insulative properties at the cost of light transmission.
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.
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.
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.
PMMA Laserdisc.