Dimethylol ethylene urea
Names | |
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Preferred IUPAC name
1,3-Bis(hydroxymethyl)imidazolidin-2-one | |
Other names
Carbamol TsEM; 1,3-Dimethylol-2-imidazolidinone, Cassurit RI[1]
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Identifiers | |
3D model (
JSmol ) |
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ChemSpider | |
ECHA InfoCard
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100.004.786 |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C5H10N2O3 | |
Molar mass | 146.146 g·mol−1 |
Appearance | White resin |
Density | 1.4±0.1 g/cm3[2] |
Melting point | 101 to 103[3] °C (214 to 217 °F; 374 to 376 K) |
Boiling point | 342.6±27 °C |
72g/L (25 °C) | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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Skin Sensitive; Suspected of causing cancer(inhalation)[4] |
Flash point | 161.0±23.7 °C[2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dimethylol ethyleneurea is an organic compound derived from formaldehyde and urea. It is a colourless solid that is used for treating cellulose-based heavy fabrics to inhibit wrinkle formation.[5] Dimethylol ethylene urea (DMEU) bonds with the hydroxyl groups present in long cellulose chains and prevents the formation hydrogen bonding between the chains, the primary cause of wrinkling.[6] This treatment produces permanently wrinkle-resistant fabrics and is different from the effects achieved from using fabric softeners. An additional names for DMEU includes 1,3-bis(hydroxymethyl)-tetrahydro-2-imidazolone.[7]
Mechanism
Wrinkles form in cotton fabrics due to the free
As seen in the figure, this formation of a C-O bond through a dehydration reaction (loss of water) allows the fabric to be bleached and heated to reasonable temperatures without fear of breaking the C-O bonds formed.
DMEU is applied industrially to the fabric after all the creases desired for design are in place. The fabric is heated and a DMEU resin is slathered on to the fabric. Depending on the procedure, the residue may contain metal catalysts or acid catalysts to help with the reaction. The utilization of DMEU in conjunction with a small concentration of tetraethoxysilane (TEOS) helps to improve the tensile strength of the treated material and decreases the yellowing of the material[8]
Production
The production of DMEU is through the condensation of formaldehyde with ethylene urea:[9]
- 2CH2O + (C2H4N2H2)CO → (C2H2N2(CH2OH)2)CO
The reaction proceeds around 200 °C (392 °F) but this temperature can be brought down to around 70 °C (158 °F) in the presence of an acid
History
Before the development of DMEU, formaldehyde and its derivatives were used as anti-wrinkle agents.. After contact with
The five member ring structure of DMEU, a 2-imidazolidone, resists attack by chlorine during bleaching. As an additional advantage, DMEU can be used to treat fabrics at relatively mild conditions and is odorless. The use of DMEU on cotton was patented by Rohm and Haas Co. in 1941. As suitable as DMEU was as an anti-wrinkle agent, it decreases dramatically the tensile strength of the fabric. Because DMEU inhibited new hydrogen bond formation, it also hindered the spreadability of cotton fibers under pressure. This problem regarding the loss of tensile strength is common amongst cotton treatments. Another common problem from treatment of DMEU is the yellowing of the treated fabric, because of the acidic conditions with high amounts of heat.[12] Currently, DMEU is used along with other formaldehyde urea derivatives for cotton fabrics of varying tear strength, color, softness, and ease of care.
Many DMEU-related cyclic urea derivatives used to synthesize urea-formaldehyde resins also have applications in treating paper, but DMEU has not proven useful in this regard.[13]
Health concerns
DMEU is a formaldehyde derivative and thus has been known to cause irritation of the skin and allergic reactions from those who are exposed to the resin for extended periods of time. DMEU is a mild irritant and if consumed in moderate quantities may have adverse effects on the body. Additionally, DMEU is considered carcinogenic to humans based its inclusion as a formaldehyde derivative. In 2004 the WHO International Agency for Research on Cancer designated formaldehyde as a carcinogen, making all of its derivatives also carcinogenic.[14] As a result of these health concerns there are alternate areas of research in ionic crosslinking compounds as opposed to DMEU and other formaldehyde-based crosslinking compounds.[15]
References
- ^ "Dimethylol ethylene urea".
- ^ a b "Dimethylol ethylene urea | C5H10N2O3 | ChemSpider".
- Shell Internationale Research
- ^ "C&L Inventory".
- ISBN 978-3527306732.
- ^ "2-Imidazolidinone,1,3-bis(hydroxymethyl)-". www.chemsrc.com. Retrieved 2022-11-16.
- ISSN 0021-8995.
- ^ US 2825732, Wayland Jr., Rosser Lee, "Manufacture of ethylene urea and the dimethylol derivative thereof", published 1958-03-04, assigned to Dan River Mills Inc.
- S2CID 96704213.
- Du Pont
- ISSN 0144-8617.
- . Retrieved 13 November 2021.
- S2CID 202028527.
- ^ Hariharrao, Vargantwar, Pruthesh (2008-05-03). "Preparation of Ionic Cellulose for Wrinkle Resistant Fabrics".
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(help)CS1 maint: multiple names: authors list (link)
Further reading
- Vargantwar, P. H. Preparation of Ionic Cellulose for Wrinkle Resistant Fabrics. 2007. North Carolina State University: Textile Chemistry. Masters Thesis
- Petersen, H. (1968). "Reaction Mechanisms, Structure, and Properties of Methylol Compounds in Cross-Linking Cotton1". Textile Research Journal. 38 (2): 156–176. S2CID 97906266.
- US 2898238, van Loo Jr., William Julius & Salsbury, Jason Melvin, "Process for treating textiles with ethylene urea-formaldehyde reaction products", published 1959-08-04, assigned to American Cyanamid Co.
- Reinhardt, R. M.; Harper, R. J. (1984). "A Comparison of Aftertreatments to Lower Formaldehyde Release from Cottons Crosslinked with Various Finishing Agents". Journal of Industrial Textiles. 13 (4): 216–227. S2CID 135974769.