N-Isopropyl-N'-phenyl-1,4-phenylenediamine
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N-Isopropyl-N'-phenyl-1,4-phenylenediamine
''N''-Isopropyl-''N''′-phenyl-1,4-phenylenediamine (often abbreviated IPPD) is an organic compound commonly used as an antiozonant in rubbers, particularly those used for tires. Like other p-phenylenediamine-based antiozonants it works by virtue of its low ionization energy, which allows it to react with ozone faster than ozone will react with rubber. This reaction converts it to the corresponding aminoxyl radical (R2N–O•), with the ozone being converted to a hydroperoxyl radical (HOO•), these species can then be scavenged by other antioxidant polymer stabilizers. IPPD is prone to process called blooming, where it migrates to the surface of the rubber. This can be beneficial to the tire, as ozone attacks the tire surface and blooming therefore moves the antiozonant to where it is most needed, however this also increases the leaching of IPPD into the environment. Many tire producers have moved to using 6PPD instead, as this migrates more slowly. Oxidation of IPPD convert ...
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Antiozonant
An antiozonant, also known as anti-ozonant, is an organic compound that prevents or retards damage caused by ozone. The most important antiozonants are those which prevent degradation of elastomers like rubber. A number of research projects study the application of another type of antiozonats to protect plants. Effect of ozone Many elastomers are rich in unsaturated double bonds, which can react with ozone present in the air in process known as ozonolysis. This reaction breaks the polymer chains, degrading the mechanical properties of the material. The most obvious effect of this is cracking of the elastomer (ozone cracking), which is exacerbated by mechanical stress. The rate of degradation is effected both by the chemical structure of the elastomer and the amount of ozone in the environment. Elastomers which are rich in double bonds, such as natural rubber, polybutadiene, styrene-butadiene rubber and nitrile rubber are the most sensitive to degradation, whereas butyl rubbe ...
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P-phenylenediamine
''p''-Phenylenediamine (PPD) is an organic compound with the formula C6H4(NH2)2. This derivative of aniline is a white solid, but samples can darken due to air oxidation. It is mainly used as a component of engineering polymers and composites like kevlar. It is also an ingredient in hair dyes and is occasionally used as a substitute for henna. Production PPD is produced via three routes. Most commonly, 4-nitrochlorobenzene is treated with ammonia and the resulting 4-nitroaniline is then hydrogenated: :ClC6H4NO2 + 2 NH3 → H2NC6H4NO2 + NH4Cl :H2NC6H4NO2 + 3 H2 → H2NC6H4NH2 + 2 H2O In the DuPont route, aniline is converted to diphenyltriazine, which is then converted by acid-catalysis to 4-aminoazobenzene. Hydrogenation of the latter affords PPD.Robert A. Smiley "Phenylene- and Toluenediamines" in ''Ullmann's Encyclopedia of Industrial Chemistry'', 2002, Wiley-VCH, Weinheim. Uses Precursor to polymers PPD is a precursor to aramid plastics and fibers such as ...
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Polymer Stabilizers
Polymer stabilizers (British: polymer stabilisers) are chemical additives which may be added to polymeric materials, such as plastics and rubbers, to inhibit or retard their degradation. Common polymer degradation processes include oxidation, UV degradation, UV-damage, Thermal degradation of polymers, thermal degradation, ozonolysis, combinations thereof such as photo-oxidation of polymers, photo-oxidation, as well as reactions with catalyst residues, dyes, or impurities. All of these degrade the polymer at a chemical level, via chain scission, uncontrolled recombination and cross-linking, which adversely affects many key properties such as strength, malleability, appearance and colour. Stabilizers are used at all stages of the polymer life-cycle. They allow plastic items to be produced faster and with fewer defects, extend their useful lifespan, and facilitate their recycling. However they also continue to stabilise waste plastic, causing it to remain in the environment for longer ...
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6PPD
6PPD is an organic chemical widely used as stabilising additive (or antidegradant) in rubbers, such as NR, SBR and BR; all of which are common in vehicle tires. Although it is an effective antioxidant it is primarily used because of its excellent antiozonant peformance. It is one of several antiozonants based around ''p''-phenylenediamine (PPD). Manufacturing 6PPD is prepared by reductive amination of methyl isobutyl ketone with 4-aminodiphenylamine. This produces a racemic mixture. Application 6PPD is a common rubber antiozonant, with a major application in vehicle tires. It is mobile within the rubber and is slowly forced to the surface via blooming. Here it forms a "scavenger-protective film", reacting with the ozone more quickly that the ozone can react with the rubber. This process initially forms aminoxyl radicals and was thought to stop at the quinone diimine, but is now known to continue to form quinones, amongst other products. Despite 6PPD being used in tires sinc ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Living t ...
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Tire
A tire (American English) or tyre (British English) is a ring-shaped component that surrounds a Rim (wheel), wheel's rim to transfer a vehicle's load from the axle through the wheel to the ground and to provide Traction (engineering), traction on the surface over which the wheel travels. Most tires, such as those for automobiles and bicycles, are pneumatically inflated structures, which also provide a flexible cushion that absorbs shock as the tire rolls over rough features on the surface. Tires provide a footprint, called a contact patch, that is designed to match the weight of the vehicle with the bearing strength of the surface that it rolls over by providing a bearing pressure that will not deform the surface excessively. The materials of modern pneumatic tires are synthetic rubber, natural rubber, fabric, and wire, along with carbon black and other chemical compounds. They consist of a tire tread, tread and a body. The tread provides Traction (engineering), traction ...
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Ionization Energy
Ionization, or Ionisation is the process by which an atom or a molecule acquires a negative or positive charge by gaining or losing electrons, often in conjunction with other chemical changes. The resulting electrically charged atom or molecule is called an ion. Ionization can result from the loss of an electron after collisions with subatomic particles, collisions with other atoms, molecules and ions, or through the interaction with electromagnetic radiation. Heterolytic bond cleavage and heterolytic substitution reactions can result in the formation of ion pairs. Ionization can occur through radioactive decay by the internal conversion process, in which an excited nucleus transfers its energy to one of the inner-shell electrons causing it to be ejected. Uses Everyday examples of gas ionization are such as within a fluorescent lamp or other electrical discharge lamps. It is also used in radiation detectors such as the Geiger-Müller counter or the ionization chamber. The ionizati ...
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Ozone
Ozone (), or trioxygen, is an inorganic molecule with the chemical formula . It is a pale blue gas with a distinctively pungent smell. It is an allotrope of oxygen that is much less stable than the diatomic allotrope , breaking down in the lower atmosphere to (dioxygen). Ozone is formed from dioxygen by the action of ultraviolet (UV) light and electrical discharges within the Earth's atmosphere. It is present in very low concentrations throughout the latter, with its highest concentration high in the ozone layer of the stratosphere, which absorbs most of the Sun's ultraviolet (UV) radiation. Ozone's odour is reminiscent of chlorine, and detectable by many people at concentrations of as little as in air. Ozone's O3 structure was determined in 1865. The molecule was later proven to have a bent structure and to be weakly diamagnetic. In standard conditions, ozone is a pale blue gas that condenses at cryogenic temperatures to a dark blue liquid and finally a violet-black soli ...
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Aminoxyl
Aminoxyl denotes a radical functional group with general structure R2N–O•. It is commonly known as a nitroxyl radical or a nitroxide, however IUPAC discourages the use of these terms, as they erroneously suggest the presence of a nitro group. Aminoxyls are structurally related to hydroxylamines and ''N''-oxoammonium salts, with which they can interconvert via a series of redox steps. Aminoxyl radical.svg, The general structure of the aminoxyl radical 2,2,6,6-Tetramethylpiperidinyloxyl.svg, TEMPO, a commonly encountered organic aminoxyl radical Kaliumnitrosodisulfonat.svg, Fremy's salt, an inorganic aminoxyl radical Sterically unhindered aminoxyls baring α-hydrogens are unstable and undergo rapid disproportionation to nitrones and hydroxylamines. Sterically hindered aminoxyls without α-hydrogens, such TEMPO and TEMPOL, and are persistent (stable) radicals and find use in a range of applications, both on the laboratory scale and in industry. Their ability to reversibly bi ...
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Bloom (phase)
In polymer chemistry, materials science, and food science, bloom refers to the migration of one component of a solid mixture to the surface of an article. The process is an example of phase separation or phase aggregation. Materials science Blooming is commonly encountered in polymer additives such as stabilizers. Many polymers are essentially pure hydrocarbons whereas additives are often significantly more polar, this results their being forced out via hydrophobic forces. The blooming of additives may be desirable or undesirable. For example, the migration of antioxidants to the polymer surface may help it resist degradation. Conversely, the leaching of additives from packaging materials into foods, or the blooming of additives in biomedical devices is often of high concern. Regulations exist in many counties that require both the levels of blooming and the materials involved to be of a safe level, for example the international symbol for materials approved for food contact is ...
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Leaching (chemistry)
Leaching is the process of a solute becoming detached or extracted from its carrier substance by way of a solvent. Leaching is a naturally occurring process which scientists have adapted for a variety of applications with a variety of methods. Specific extraction methods depend on the soluble characteristics relative to the sorbent material such as concentration, distribution, nature, and size. Leaching can occur naturally seen from plant substances (inorganic and organic), solute leaching in soil, and in the decomposition of organic materials. Leaching can also be applied affectedly to enhance water quality Water quality refers to the chemical, physical, and biological characteristics of water based on the standards of its usage. It is most frequently used by reference to a set of standards against which compliance, generally achieved through tr ... and contaminant removal, as well as for disposal of hazardous waste products such as fly ash, or Rare-earth element, rare ear ...
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Quinone
The quinones are a class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double bonds, resulting in "a fully Conjugated system, conjugated cyclic diketone, dione structure". The archetypical member of the class is 1,4-benzoquinone or cyclohexadienedione, often called simply "quinone" (thus the name of the class). Other important examples are 1,2-benzoquinone (''ortho''-quinone), 1,4-naphthoquinone and anthraquinone, 9,10-anthraquinone. The name is derived from that of quinic acid (with the suffix "-one" indicating a ketone), since it is one of the compounds obtained upon oxidation of quinic acid. Quinic acid, like quinine is obtained from cinchona bark, called wikt:quinaquina, quinaquina in the indigenous languages of Peruvian tribes. Properties Quinones are oxidized derivatives of aromatic compounds and are often re ...
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