N-hydroxymethyl-ureas

AMIDE-FORMALDEHYDE-REACTION-PRODUCTS 3.4.3. N-hydroxymethyl-ureas 

7V-hydroxy- methyl-urea HN-CO-NH2 C2H6N2O2 90.08 33% Solid, m.p. lire 1000-82-4 213-674-8 

The hydroxymethyl ureas are colourless, odourless and distinguished by good water solubility they release formaldehyde in water based solutions, espeeially in alkaline solutions, and therefore have been used to some extent as preservatives in alkaline funetional fluids, e.g. lubricoolants. In more neutral solutions the hydroxymethyl ureas release a small amount only of their formaldehyde content. Using hydroxymethyl ureas as preservatives one has to bear in mind that a nutrient for mierobes is left, when the formaldehyde is separated and used up by irreversible reaetions with other eompounds or mieroorganisms. 

N -bis(hydroxymethyl)thiourea — N-hydro-xymethyl-S-hydroxymethyl-thiourea 

Both tautomerie forms of thiourea can react with formaldehyde. The S-hydroxymethyl isomers are formed as the principal products under alkaline conditions however, it is not believed that the materials obtained are 100% isomerically pure (Walker, 1975). 

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Synonyms Germall 77 N-(hydroxymethyl)-N-(l,3-dihydroxy-methyl-2,5-dioxo-4-imidazolidinyl)-N -(hydroxymethyl) urea. 

CAS 78491-02-8 EINECS/ELINCS 278-928-2 Synonyms N-[1,3-Bis (hydroxymethyl)-2,5-dioxo-4-imidazolidinyl]- N,N -bis (hydroxymethyl) urea N-(Hydroxymethyl)-N-(1,3-dihydroxymethyl-2,5-dioxo-4-imidazolidinyl)-N -(hydroxymethyl) urea Imidazolidinyl urea 11 Urea, N-[1,3-bis (hydroxymethyl)-2,5-dioxo-4-imidazolidinyl-N,N -bis (hydroxymethyl)-Classification Heterocyclic substituted urea Empirical C8H14N4O7... 

Carboxy substituted diazepines 226 and 229 react with phenyl isocyanate to afford pyrimido diones 227 and 230, correspondingly (Scheme 48, Section 3.1.1.3 (1993JHC897)). N-Hydroxymethylation on an indole ring annulated to benzaze-pinone, as well as formation of the corresponding carbamate and urea, has been described (2004MI1076). 

Noxythiolin (N-hydroxy N-methylthiourea) is supplied as a dry powder and on aqueous reconstitution slowly releases formaldehyde and N-methylthiourea. The compound has extensive antibacterial and antifungal properties and is used both topically and in accessible body cavities as an irrigation solution and in the treatment of peritonitis. Polynoxylin (poly[methylenedi(hydroxymethyl) urea]) is a similar compound available in gel and lozenge formulations. 

EINECS 213-674-8 HSDB 5776 1-(Hydroxymethyl)urea Methylol urea Methylolurea Methylolureas Mono-(hydroxymethyl)urea Monomethylolurea N-(Hydroxy-methyl)urea N-Methyiolurea NSC 13181 Urea, (hydroxymethyl)-, Used In manufacture of urea-formaldehyde resins. Colorless crystals mp = 111 soluble H20, EtCH, MeOH, AoOH, insoluble in Et20. 

Bishydroxymethyl urea N,N -Bis(hydroxymethyl) urea. See Dimethylol urea... 

CAS 140-95-4 EINECS/ELINCS 205-444-0 Synonyms 1,3-Bishydroxymethyl urea N,N-Bis(hydroxymethyl) urea N,N -Dihydroxymethylurea 1,3-Dimethylolurea DMU Methurol Oxymethurea Empirical CjHsNjOj Formula HOCH2NHCONHCH2OH... 

N,N -bis(hydroxymethyl)-urea Dimethylol urea, dihydroxymethylurea, dimethylurea, urea formaldehyde 17 103... 

Synonyms Germall II N-(i,3-bis(hydroxymethyl)-2,5-dioxo-4-imidazolidinyI)-JVvN -bis(hydroxymethyl) urea diazolidinyl urea Uses preservative used in cosmetic creams, lotions, shampoos, hair gels, etc. (Germall II)... 

Amides derive also from carbonic acid. The hemiamide of carbonic acid = carbamic acid (H2N-COOH) cannot be in existence it degrades spontaneously to CO2 and NH3. However, salts and esters of carbamic acid are more or less stable. The esters, H2N-COOR, are named urethanes. They react with ammonia to urea, the diamide of carbonic acid, (NH2)2C = 0. Urethanes and urea add readily formaldehyde forming N-hydroxymethyl or N,N -bis-hydroxymethyl derivatives which are formaldehyde releasing compounds. 

U rea-formaldehyde N,N -Bis(hydroxymethyl)urea Crosslinking, polymer formation... 

N,]S7-bis(methoxymethyl)uron was first isolated and described in 1936 (41), but was commercialized only in 1960. It is manufactured (42) by the reaction of 4 mol of formaldehyde with 1 mol of urea at 60°C under highly alkaline conditions to form tetramethylolurea [2787-01-1]. After concentration under reduced pressure to remove water, excess methanol is charged and the reaction continued under acidic conditions at ambient temperatures to close the ring and methylate the hydroxymethyl groups. After filtration to remove the precipitated salts, the methanolic solution is concentrated to recover excess methanol. The product (75—85% pure) is then mixed with a methylated melamine—formaldehyde resin to reduce fabric strength losses in the presence of chlorine, and diluted with water to 50—75% soHds. Uron resins do not find significant use today due to the greater amounts of formaldehyde released from fabric treated with these resins. 

Further routes of cyclizations have been studied in parallel in the case of cis- and rra/J5-2-hydroxymethyl-l-cyclohexylamine (106) (880PP73). The preparation of thiourea or urea adducts 107 and 108 with phenyl isothiocyanate or phenyl isocyanate proceeds smoothly. The reaction of 107 with methyl iodide and subsequent alkali treatment, by elimination of methyl mercaptan, resulted in the iminooxazine 109 in high yields. The ring closures of both cis and trans thiourea adducts to 1,3-oxazines proceed with retention. Cyclodesulfuration of the adduct 107 by mercury(II) oxide or N,N -dicyclohexylcarbodiimide resulted in the iminooxazine 109, but the yield was low and the purification of the product was cumbersome. The ring closure of 108 with thionyl chloride led to the iminooxazine 109 in only moderate yield. 

Biopure 100 Germall 115 imidazolidinyl urea methanebis[N,N (5-ureido-2,4-diketotetrahydroimidazole)-N,N-dimethylol] l,l -methylenebis 3-[3-(hydroxymethyl)-2,5-dioxo-4-imidazolidinyI]urea Tri-Stat IJJ. 

Urea (W16) and tris(hydroxymethyl)aminomethane (R18) have been recommended as convenient stable primary N standards for protein N analysis. 

Urea, N-(1,3-bis(hydroxymethyl)-2,5-dioxo-4-imidazol-idinyl)-N,N -bis(hydroxymethyl)-. 

Methylenebis(N -(1-(hydroxymethyl)-2,5-dioxo-4-imidazolidinyl)urea) Sept 115 Tristat 1U Unicide U-13 Urea, N,N"-methylene-bis(N -(1-(hydroxymethyl)-2,5-dioxo-4-imidazolidinyl)yl)-urea. Antimicrobial preservative used in cosmetics. 3V Sutton Labs. 

Synonyms Urea, (2,5-dioxo-4-imidazolydinyl)-, compd. with N-(3-hydroxymethyl-3-methyl-2-hydroxybutanoyl)-3-aminopropanoic... 

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