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Names | |
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IUPAC name 4-(methylamino)phenol sulfate | |
Other names N-methyl-p-aminophenol sulfate, Pictol, p-(methylamino)phenol sulfate, monomethyl-p-aminophenol hemisulfate, Metol, Elon, Rhodol, Enel, Viterol, Scalol, Genol, Satrapol, Photol. | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.000.216 |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
(C7H10NO)2SO4 | |
Molar mass | 344.38 g/mol |
Melting point | 260 °C (500 °F; 533 K) |
Hazards | |
GHS labelling: [1] | |
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Warning | |
H302, H317, H373, H410 | |
P260, P280, P301+P312+P330 | |
Safety data sheet (SDS) | Oxford MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Metol (or Elon) is a trade name for the organic compound with the formula [HOC6H4NH2(CH3)]2HSO4. It is the sulfate salt of N-methylaminophenol. This colourless salt is a popular photographic developer used in monochrome photography. [2]
Several methods exist for the preparation of N-methylaminophenol. It arises by decarboxylation of N-4-hydroxyphenylglycine (Glycin). It can be obtained by reaction of hydroquinone with methylamine. [3]
Being an electron-rich arene, metol is readily degraded by hydrogen peroxide. [4]
Metol is an excellent developing agent for most continuous tone developer applications, and it has been widely used in published developer formulas as well as commercial products. However, it is difficult to produce highly concentrated developer solutions using Metol, and therefore most Metol developers are supplied in dry chemical mix. A developer containing both Metol and hydroquinone is called an MQ developer. This combination of agents provides greater developer activity since the rate of development by both agents together is greater than the sum of rates of development by each agent used alone (superadditivity). This combination is very versatile; by varying the quantities of Metol, hydroquinone, and restrainer, and adjusting the pH, the entire range of continuous tone developers can be made. Therefore, this form of Metol replaced most other developing agents except for hydroquinone, Phenidone (which is more recent than Metol), and derivatives of Phenidone. Notable formulas include Eastman Kodak D-76 film developer, D-72 print developer, and D-96 motion picture negative developer.
Alfred Bogisch, working for a chemical company owned by Julius Hauff, discovered in 1891 that methylated p-aminophenol has more vigorous developing action than p-aminophenol. Hauff introduced this compound as a developing agent. The exact composition of Bogisch and Hauff's early Metol is unknown, but it was most likely methylated at the ortho position of the benzene ring (p-amino-o-methylphenol), rather than at the amino group. Some time later, Metol came to mean the N-methylated variety, and the o-methylated variety fell out of use. Aktien-Gesellschaft für Anilinfabrikation (AGFA) sold this compound under the trade name Metol, which became by far the most common name, followed by Eastman Kodak's trade name Elon.
Because it has been in use for this purpose for over 100 years, and often by amateur photographers, there is a substantial body of evidence regarding the health problems that contact with Metol can cause. These are principally local dermatitis of the hands and forearms. There is also some evidence of sensitization dermatitis. [5]
Photographic processing or photographic development is the chemical means by which photographic film or paper is treated after photographic exposure to produce a negative or positive image. Photographic processing transforms the latent image into a visible image, makes this permanent and renders it insensitive to light.
4-Aminobenzoic acid (also known as para-aminobenzoic acid or PABA because the two functional groups are attached to the benzene ring across from one another in the para position) is an organic compound with the formula H2NC6H4CO2H. PABA is a white crystalline solid, although commercial samples can appear gray. It is slightly soluble in water. It consists of a benzene ring substituted with amino and carboxyl groups. The compound occurs extensively in the natural world.
In the processing of photographic films, plates or papers, the photographic developer is one or more chemicals that convert the latent image to a visible image. Developing agents achieve this conversion by reducing the silver halides, which are pale-colored, into silver metal, which is black when in the form of fine particles. The conversion occurs within the gelatine matrix. The special feature of photography is that the developer acts more quickly on those particles of silver halide that have been exposed to light. When left in developer, all the silver halides will eventually be reduced and turn black. Generally, the longer a developer is allowed to work, the darker the image.
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.
Haptens are small molecules that elicit an immune response only when attached to a large carrier such as a protein; the carrier may be one that also does not elicit an immune response by itself. The mechanisms of absence of immune response may vary and involve complex immunological interactions, but can include absent or insufficient co-stimulatory signals from antigen-presenting cells.
The gelatin silver process is the most commonly used chemical process in black-and-white photography, and is the fundamental chemical process for modern analog color photography. As such, films and printing papers available for analog photography rarely rely on any other chemical process to record an image. A suspension of silver salts in gelatin is coated onto a support such as glass, flexible plastic or film, baryta paper, or resin-coated paper. These light-sensitive materials are stable under normal keeping conditions and are able to be exposed and processed even many years after their manufacture. The "dry plate" gelatin process was an improvement on the collodion wet-plate process dominant from the 1850s–1880s, which had to be exposed and developed immediately after coating.
Acetanilide is the organic compound with the formula C6H5NHC(O)CH3. It is the N-acetylated derivative of aniline. It is an odourless solid chemical of leaf or flake-like appearance. It is also known as N-phenylacetamide, acetanil, or acetanilid, and was formerly known by the trade name Antifebrin.
Cellulose triacetate, triacetate, CTA or TAC is a chemical compound produced from cellulose and a source of acetate esters, typically acetic anhydride. Triacetate is commonly used for the creation of fibres and film base. It is chemically similar to cellulose acetate. Its distinguishing characteristic is that in triacetate, at least "92 percent of the hydroxyl groups are acetylated." During the manufacture of triacetate, the cellulose is completely acetylated; whereas in normal cellulose acetate or cellulose diacetate, it is only partially acetylated. Triacetate is significantly more heat resistant than cellulose acetate.
Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two hydroxyl groups bonded to a benzene ring in a para position. It is a white granular solid. Substituted derivatives of this parent compound are also referred to as hydroquinones. The name "hydroquinone" was coined by Friedrich Wöhler in 1843.
Pyrogallol is an organic compound with the formula C6H3(OH)3. It is a water-soluble, white solid although samples are typically brownish because of its sensitivity toward oxygen. It is one of three isomers of benzenetriols.
Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines.
1,4-Benzoquinone, commonly known as para-quinone, is a chemical compound with the formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic or formaldehyde. This six-membered ring compound is the oxidized derivative of 1,4-hydroquinone. The molecule is multifunctional: it exhibits properties of a ketone, being able to form oximes; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions, especially those typical for α,β-unsaturated ketones. 1,4-Benzoquinone is sensitive toward both strong mineral acids and alkali, which cause condensation and decomposition of the compound.
Glycin, or N-(4-hydroxyphenyl)glycine, is N-substituted p-aminophenol. It is a photographic developing agent used in classic black-and-white developer solutions. It is not identical to, but derived from glycine, the proteinogenic amino acid. It is typically characterized as thin plates of white or silvery powder, although aged samples appear brown. It is sparingly soluble in water and most organic solvents; it is readily soluble in alkalies and acids.
4-Aminophenol (or para-aminophenol or p-aminophenol) is an organic compound with the formula H2NC6H4OH. Typically available as a white powder, it is commonly used as a developer for black-and-white film, marketed under the name Rodinal.
Photographic developer solutions may contain more than one developing agents, such as Metol and hydroquinone, or Phenidone and hydroquinone. This is because they work together to a synergistic effect, called superadditive development.
Photographic emulsion is a light-sensitive colloid used in film-based photography. Most commonly, in silver-gelatin photography, it consists of silver halide crystals dispersed in gelatin. The emulsion is usually coated onto a substrate of glass, films, paper, or fabric. The substrate is often flexible and known as a film base.
Phenidone (1-phenyl-3-pyrazolidinone) is an organic compound that is primarily used as a photographic developer. It has five to ten times the developing power as Metol, capable of achieving the same level of development in both less time and at a lower concentration. It also has low toxicity and unlike some other developers, does not cause dermatitis upon skin contact. As a developer, Phenidone is typically used in conjunction with hydroquinone for black and white photography and performs better at lower pH levels.
FX-55 is an 'eco-friendly' photographic developer for monochrome film devised by Geoffrey Crawley. It was first published in Amateur Photographer.
Xtol is a photographic developer manufactured by Eastman Kodak company.
N-Hydroxyphthalimide is the organic compound with the formula C6H4(CO)2NOH. A white or yellow solid, it is a derivative of phthalimide. The compound is as a catalyst in the synthesis of other organic compounds. It is soluble in water and organic solvents such as acetic acid, ethyl acetate and acetonitrile.