Guanamine

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Structure of guanamines, R = alkyl, aryl, etc. GuanamineGeneral.svg
Structure of guanamines, R = alkyl, aryl, etc.

In organic chemistry, a guanamine is an organic compound with the formula (H2NC)2N3CR[ further explanation needed ]. They are heterocycles of the triazine class. Guanamines are closely related to melamine ((H2NC)3N3), except with one amino substituent replaced by an organic group. With two amines, guanamines are bifunctional, whereas melamine is trifunctional. This difference is exploited in the use of guanamines to modify the crosslink density in melamine resins. They are white or colorless solids of low toxicity. [1]

Some popular guanamines are the phenyl, methyl and nonyl derivatives, called benzoguanamine, acetoguanamine, and capriguanamine. They are all prepared by the condensation of cyanoguanidine with the corresponding nitrile: [2]

(H2N)2C=NCN + RCN → (CNH2)2(CR)N3

Related Research Articles

In chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine.

<span class="mw-page-title-main">Thermosetting polymer</span> Polymer obtained by irreversibly hardening (curing) a resin

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<span class="mw-page-title-main">Melamine</span> Fire-resistant chemical used in dinnerware, insulation, and cleaning products

Melamine is an organic compound with the formula C3H6N6. This white solid is a trimer of cyanamide, with a 1,3,5-triazine skeleton. Like cyanamide, it contains 67% nitrogen by mass, and its derivatives have fire-retardant properties due to its release of nitrogen gas when burned or charred. Melamine can be combined with formaldehyde and other agents to produce melamine resins. Such resins are characteristically durable thermosetting plastic used in high pressure decorative laminates such as Formica, melamine dinnerware including cooking utensils, plates, plastic products, laminate flooring, and dry erase boards. Melamine foam is used as insulation, soundproofing material and in polymeric cleaning products, such as Magic Eraser.

<span class="mw-page-title-main">Peptide synthesis</span> Production of peptides

In organic chemistry, peptide synthesis is the production of peptides, compounds where multiple amino acids are linked via amide bonds, also known as peptide bonds. Peptides are chemically synthesized by the condensation reaction of the carboxyl group of one amino acid to the amino group of another. Protecting group strategies are usually necessary to prevent undesirable side reactions with the various amino acid side chains. Chemical peptide synthesis most commonly starts at the carboxyl end of the peptide (C-terminus), and proceeds toward the amino-terminus (N-terminus). Protein biosynthesis in living organisms occurs in the opposite direction.

In chemistry, solid-phase synthesis is a method in which molecules are covalently bound on a solid support material and synthesised step-by-step in a single reaction vessel utilising selective protecting group chemistry. Benefits compared with normal synthesis in a liquid state include:

<span class="mw-page-title-main">Cyanuric acid</span> Chemical compound belonging to the class of triazine

Cyanuric acid or 1,3,5-triazine-2,4,6-triol is a chemical compound with the formula (CNOH)3. Like many industrially useful chemicals, this triazine has many synonyms. This white, odorless solid finds use as a precursor or a component of bleaches, disinfectants, and herbicides. In 1997, worldwide production was 160 000 tonnes.

<span class="mw-page-title-main">Triazine</span> Aromatic, heterocyclic compound

Triazines are a class of nitrogen-containing heterocycles. The parent molecules' molecular formula is C3H3N3. They exist in three isomeric forms, 1,3,5-triazines being common.

1,3,5-Triazine, also called s-triazine, is an organic chemical compound with the formula (HCN)3. It is a six-membered heterocyclic aromatic ring, one of several isomeric triazines. S-triazine—the "symmetric" isomer—and its derivatives are useful in a variety of applications.

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<span class="mw-page-title-main">Thiosemicarbazone</span> Class of chemical compounds

A thiosemicarbazone is an organosulfur compound with the formula H2NC(S)NHN=CR2. Many variations exist, including those where some or all of the NH centers are substituted by organic groups. Thiosemicarbazones are usually produced by condensation of a thiosemicarbazide with an aldehyde or ketone:

<span class="mw-page-title-main">Melamine resin</span> Hard, thermosetting plastic material often used in dinnerware

Melamine resin or melamine formaldehyde is a resin with melamine rings terminated with multiple hydroxyl groups derived from formaldehyde. This thermosetting plastic material is made from melamine and formaldehyde. In its butylated form, it is dissolved in n-butanol and xylene. It is then used to cross-link with alkyd, epoxy, acrylic, and polyester resins, used in surface coatings. There are many types, varying from very slow to very fast curing.

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

Aminoethylpiperazine (AEP) is a derivative of piperazine. This ethyleneamine contains three nitrogen atoms; one primary, one secondary and one tertiary. It is a corrosive organic liquid and can cause second or third degree burns. Aminoethylpiperazine can also cause pulmonary edema as a result of inhalation. It is REACH and TSCA registered.

2-Cyanoguanidine is a nitrile derived from guanidine. It is a dimer of cyanamide, from which it can be prepared. 2-Cyanoguanidine is a colourless solid that is soluble in water, acetone, and alcohol, but not nonpolar organic solvents.

A thermoset polymer matrix is a synthetic polymer reinforcement where polymers act as binder or matrix to secure in place incorporated particulates, fibres or other reinforcements. They were first developed for structural applications, such as glass-reinforced plastic radar domes on aircraft and graphite-epoxy payload bay doors on the Space Shuttle.

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

Acetoguanamine is an organic compound with the chemical formula (CNH2)2CCH3N3. It is related to melamine but with one amino group replaced by methyl. Acetoguanamine is used in the manufacturing of melamine resins. Unlike melamine ((CNH2)3N3), acetoguanamine is not a crosslinker. The "aceto" prefix is historical, the compound does not contain an acetyl group. A related compound is benzoguanamine.

Impregnation resins are slightly viscous, organic liquids that are used in the forest products industry for wood modification. They typically contain formaldehyde and are composed of dimers and trimers of the main molecule. These can become polymer solutions upon curing inside of a wood substrate, imparting stabilizing properties. Impregnation of these resins involves a vacuum chamber procedure that completely disperses the resin into the wood. Once inside of the wood, the resin can diffuse into the cell wall and enhance the physical strength of the wood even further.

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

Triuret is an organic compound with the formula (H2NC(O)NH)2CO. It is a product from the pyrolysis of urea. Triuret is a colorless, crystalline, hygroscopic solid, slightly soluble in cold water or ether, and more soluble in hot water. It is a planar molecule. The central carbonyl is hydrogen-bonded to both terminal amino groups.

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

Benzoguanamine is an organic compound with the chemical formula (CNH2)2(CC6H5)N3. It is related to melamine but with one amino group replaced by phenyl. Benzoguanamine is used in the manufacturing of melamine resins. Unlike melamine ((CNH2)3N3), benzoguanamine is not a crosslinker. The "benzo" prefix is historical, as the compound contains phenyl, not a benzo group. A related compound is acetoguanamine.

Dimethylene triurea (DMTU) is the organic compound with the formula (H2NC(O)NHCH2NH)2CO. It is a white water-soluble solid. The compound is formed by the condensation of formaldehyde with urea. Both branched and linear isomers exist.

<span class="mw-page-title-main">Methylol urea</span> Chemical compound

Methylol urea is the organic compound with the formula H2NC(O)NHCH2OH. It is a white, water-soluble solid that decomposes near 110 °C.

References

  1. H. Deim; G. Matthias; R. A. Wagner (2012). "Amino Resins". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_115.pub2. ISBN   978-3-527-30673-2.
  2. J. K. Simons; M. R. Saxton (1953). "Benzoguanamine". Org. Synth. 33: 13. doi:10.15227/orgsyn.033.0013.