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] | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.004.786 |
EC Number |
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PubChem CID | |
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 | 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). |
Dimethylol ethylene urea 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]
Wrinkles form in cotton fabrics due to the free hydroxyl groups. Cotton is a form of cellulose chains linked to form firm three-dimensional structures that offer both tensile strength and flexibility due to their carbon-carbon and carbon-oxygen bond based backbone. Since cellulose is composed of glucose units, cyclic carbohydrate molecules, cellulose has free hydroxyl groups (-OH) projecting from each monomeric subunit. These hydroxyl groups tend form hydrogen-bonds to neighboring hydroxyl groups. When the fabric is stressed either by heat or pressure, the original hydrogen bonds in the cotton fabric break and reform with nearby atoms at random. This re-forming of the hydrogen bonds, known as cross linking, is the reason for wrinkles, or creases, in the fabric. DMEU works to prevent these wrinkles by covalently bonding to two free hydroxyl groups in the fabric through a dehydration reaction that is not as easily broken as the hydrogen bond before treatment.
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]
The production of DMEU is through the condensation of formaldehyde with ethylene urea: [9]
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 catalyst. [10] Ethylene urea, sodium hydroxide, and paraformaldehyde are often dissolved in methanol during the synthesis of DMEU. [11]
Before the development of DMEU, formaldehyde and its derivatives were used as anti-wrinkle agents.. After contact with chlorine bleaches at high temperatures, however, the treated fabric released hydrochloric acid, which degraded the fabric. Additionally, formaldehyde evaporates easily and is pungent. The search for stabler alternatives to formaldehyde led to dimethylol formaldehyde derivatives such as DMEU.
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]
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]
Cellulose is an organic compound with the formula (C
6H
10O
5)
n, a polysaccharide consisting of a linear chain of several hundred to many thousands of β(1→4) linked D-glucose units. Cellulose is an important structural component of the primary cell wall of green plants, many forms of algae and the oomycetes. Some species of bacteria secrete it to form biofilms. Cellulose is the most abundant organic polymer on Earth. The cellulose content of cotton fiber is 90%, that of wood is 40–50%, and that of dried hemp is approximately 57%.
Formaldehyde ( for-MAL-di-hide, fər-) (systematic name methanal) is an organic compound with the chemical formula CH2O and structure H−CHO, more precisely H2C=O. The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as aqueous solutions (formalin), which consists mainly of the hydrate CH2(OH)2. It is the simplest of the aldehydes (R−CHO). As a precursor to many other materials and chemical compounds, in 2006 the global production of formaldehyde was estimated at 12 million tons per year. It is mainly used in the production of industrial resins, e.g., for particle board and coatings. Small amounts also occur naturally.
In organic chemistry, an acetal is a functional group with the connectivity R2C(OR')2. Here, the R groups can be organic fragments or hydrogen, while the R' groups must be organic fragments not hydrogen. The two R' groups can be equivalent to each other or not. Acetals are formed from and convertible to aldehydes or ketones and have the same oxidation state at the central carbon, but have substantially different chemical stability and reactivity as compared to the analogous carbonyl compounds. The central carbon atom has four bonds to it, and is therefore saturated and has tetrahedral geometry.
In chemistry, a hydration reaction is a chemical reaction in which a substance combines with water. In organic chemistry, water is added to an unsaturated substrate, which is usually an alkene or an alkyne. This type of reaction is employed industrially to produce ethanol, isopropanol, and butan-2-ol.
In materials science, a thermosetting polymer, often called a thermoset, is a polymer that is obtained by irreversibly hardening ("curing") a soft solid or viscous liquid prepolymer (resin). Curing is induced by heat or suitable radiation and may be promoted by high pressure or mixing with a catalyst. Heat is not necessarily applied externally, and is often generated by the reaction of the resin with a curing agent. Curing results in chemical reactions that create extensive cross-linking between polymer chains to produce an infusible and insoluble polymer network.
In biochemistry, cellulose acetate refers to any acetate ester of cellulose, usually cellulose diacetate. It was first prepared in 1865. A bioplastic, cellulose acetate is used as a film base in photography, as a component in some coatings, and as a frame material for eyeglasses; it is also used as a synthetic fiber in the manufacture of cigarette filters and playing cards. In photographic film, cellulose acetate film replaced nitrate film in the 1950s, being far less flammable and cheaper to produce.
A diol is a chemical compound containing two hydroxyl groups. An aliphatic diol may also be called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. They are used as protecting groups of carbonyl groups, making them essential in synthesis of organic chemistry.
Urea-formaldehyde (UF), also known as urea-methanal, so named for its common synthesis pathway and overall structure, is a nontransparent thermosetting resin or polymer. It is produced from urea and formaldehyde. These resins are used in adhesives, plywood, particle board, medium-density fibreboard (MDF), and molded objects. In agriculture, urea-formaldehyde compounds are one of the most commonly used types of slow-release fertilizer.
Hot-melt adhesive (HMA), also known as hot glue, is a form of thermoplastic adhesive that is commonly sold as solid cylindrical sticks of various diameters designed to be applied using a hot glue gun. The gun uses a continuous-duty heating element to melt the plastic glue, which the user pushes through the gun either with a mechanical trigger mechanism on the gun, or with direct finger pressure. The glue squeezed out of the heated nozzle is initially hot enough to burn and even blister skin. The glue is sticky when hot, and solidifies in a few seconds to one minute. Hot-melt adhesives can also be applied by dipping or spraying, and are popular with hobbyists and crafters both for affixing and as an inexpensive alternative to resin casting.
In polymer chemistry, branching is the regular or irregular attachment of side chains to a polymer's backbone chain. It occurs by the replacement of a substituent on a monomer subunit by another covalently-bonded chain of that polymer; or, in the case of a graft copolymer, by a chain of another type. Branched polymers have more compact and symmetrical molecular conformations, and exhibit intra-heterogeneous dynamical behavior with respect to the unbranched polymers. In crosslinking rubber by vulcanization, short sulfur branches link polyisoprene chains into a multiple-branched thermosetting elastomer. Rubber can also be so completely vulcanized that it becomes a rigid solid, so hard it can be used as the bit in a smoking pipe. Polycarbonate chains can be crosslinked to form the hardest, most impact-resistant thermosetting plastic, used in safety glasses.
Wood glue is an adhesive used to tightly bond pieces of wood together. Many substances have been used as glues. Traditionally animal proteins like casein from milk or collagen from animal hides and bones were boiled down to make early glues. They worked by solidifying as they dried. Later, glues were made from plant starches like flour or potato starch. When combined with water and heated, the starch gelatinizes and forms a sticky paste as it dries. Plant-based glues were common for books and paper products, though they can break down more easily over time compared to animal-based glues. Examples of modern wood glues include polyvinyl acetate (PVA) and epoxy resins. Some resins used in producing composite wood products may contain formaldehyde. As of 2021, “the wood panel industry uses almost 95% of synthetic petroleum-derived thermosetting adhesives, mainly based on urea, phenol, and melamine, among others”.
Methyl carbamate (also called methylurethane, or urethylane) is an organic compound and the simplest ester of carbamic acid (H2NCO2H). It is a colourless solid.
Ruth Mary Rogan Benerito was an American physical chemist and inventor known for her huge impact work related to the textile industry, notably including the development of wash-and-wear cotton fabrics using a technique called cross-linking. She held 55 patents.
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.
Tetrakis(hydroxymethyl)phosphonium chloride (THPC) is an organophosphorus compound with the chemical formula [P(CH2OH)4]Cl. It is a white water-soluble salt. THPC has applications as a precursor to fire-retardant materials, as well as a microbiocide in commercial and industrial water systems.
Ironing is the use of an iron, usually heated, to remove wrinkles and unwanted creases from fabric. The heating is commonly done to a temperature of 180–220 °C (360–430 °F), depending on the fabric. Ironing works by loosening the bonds between the long-chain polymer molecules in the fibres of the material. While the molecules are hot, the fibres are straightened by the weight of the iron, and they hold their new shape as they cool. Some fabrics, such as cotton, require the addition of water to loosen the intermolecular bonds. Many modern fabrics are advertised as needing little or no ironing. Permanent press clothing was developed to reduce the ironing necessary by combining wrinkle-resistant polyester with cotton.
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.
The wet strength of paper and paperboard is a measure of how well the web of fibers holding the paper together can resist a force of rupture when the paper is wet. Wet strength is routinely expressed as the ratio of wet to dry tensile force at break.
Wet Processing Engineering is one of the major streams in Textile Engineering or Textile manufacturing which refers to the engineering of textile chemical processes and associated applied science. The other three streams in textile engineering are yarn engineering, fabric engineering, and apparel engineering. The processes of this stream are involved or carried out in an aqueous stage. Hence, it is called a wet process which usually covers pre-treatment, dyeing, printing, and finishing.
Wrinkle-resistant or permanent press or durable press is a finishing method for textiles that avoids creases and wrinkles and provides a better appearance for the articles. Most cellulosic fabrics and blends of cellulosic rich fabrics tend to crease or wrinkle. A durable press finish makes them dimensionally stable and crease free. The finishing includes chemical finishing as well as mechanical finishing. Wrinkle-resistant finishes were developed in the early 20th century, as a way to deal with fabrics derived from cotton, rayon, and linen, which were found to wrinkle easily and retain the wrinkles. These treatments have a lasting effect on the fabric. Synthetics like polyester, nylon, acrylic and olefin, have a natural resistance to wrinkles and a greater stability since they do not absorb water as efficiently.
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