DMDM Hydantoin
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DMDM Hydantoin
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CAS No:
6440-58-0
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Formula:
C7H12N2O4
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Chemical Name:
DMDM Hydantoin
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Synonyms:
2,4-Imidazolidinedione,1,3-bis(hydroxymethyl)-5,5-dimethyl-;Hydantoin,1,3-bis(hydroxymethyl)-5,5-dimethyl-;1,3-Bis(hydroxymethyl)-5,5-dimethyl-2,4-imidazolidinedione;1,3-Bis(hydroxymethyl)-5,5-dimethylhydantoin;Dimethylol-5,5-dimethylhydantoin;N,N′-Dimethylol-5,5-dimethylhydantoin;DMDMH;DMDM Hydantoin;Dantoin DMDMH 55;1,3-Dimethylol-5,5-dimethylhydantoin;DMDMH 55;Glydant;Glydant XL 1000;Dantogard 2000;1,3-Dihydroxymethyl-5,5-dimethylhydantoin;Gidol;Dantogard;Surcide DMH;Mackstat DM;Nipaguard DMDMH;Dekafald;1,3-Bis(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione;Glydant LTD;Mergal 395;K 2000;K 2000 (preservative)
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CAS No:
DMDM Hydantoin Basic Attributes
188.18
188.18
229-222-8
BYR0546TOW
DTXSID8035217
Solid|Powder
2933990090
Characteristics
81.1
-0.2
Liquid
0.4 g/cu cm at 21 deg C /OECD Guideline 109/
1.00-2.5 °C
198-200 deg C, decomposes with boiling
137.5±30.7 °C
1.529
In ethanol, 56.4 g/100 cc; in hexane, 0.02 g/100 cc
Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water.
9.0X10-8 mm Hg at 25 deg C
Odorless
Henry's Law constant = 2.9X10-14 atm-cu m/mol at 25 °C (est)
pKa1 = 13.43, pKa2 = 13.41 (est)
Compatible with cationic, anionic and nonionic surfactants|Hydroxyl radical reaction rate constant = 3.0X10-11 cu cm/molec-sec at 25 °C (est)
Safety Information
22-36-43
26-36/37
Xi,Xn
P261, P264, P270, P271, P272, P280, P285, P301+P312, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P330, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, P501
H302
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.|Do not discharge effluent containing this product into lakes, streams, ponds, estuaries, oceans or other waters unless in accordance with the requirements of a National Pollutant Discharge Elimination System (NPDES) permit and the permitting authority has been notified in writing prior to discharge. Do not discharge effluent containing this product to sewer systems without previously notifying the local sewage treatment plant authority...Do not discharge effluent containing this product into lakes, streams, ponds, estuaries, oceans or other waters unless in accordance with the requirements of a National Pollutant Discharge Elimination System (NPDES) permit and the permitting authority has been notified in writing prior to discharge. Do not discharge effluent containing this product to sewer systems without previously notifying the local sewage treatment plant authority.../Dantogard XL-1000/|Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal.|Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it.|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.
Cosmetic Ingredient Review Panel; Final Report on the Safety Assessment of DMDM Hydantoin. J Am Coll Toxicol 7 (3): 245-77 (1988)
|Danger|H302 (71.61%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P272, P280, P285, P301+P312, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P330, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 619 companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, P362, P363, and P501
Corrosive. Causes irreversible eye damage. Harmful if swallowed, inhaled or absorbed through the skin. Do not get in eyes or on skin or on clothing. Wear goggles or face shield and chemical resistant gloves when handling. /Dantogard XL-1000/
If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label.|After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide. To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash.
Wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores.|Wash thoroughly with soap and water after handling. Remove contaminated clothing and wash contaminated clothing before reuse. /Dantogard XL-1000/|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.|SRP: Contaminated protective clothing should be segregated in a manner such that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.
Toxicity
IDENTIFICATION AND USE: DMDM hydantoin is a cosmetic preservative. It is described as being a broad-spectrum antimicrobial agent, effective against fungi, yeast, and gram-positive and gram-negative bacteria. HUMAN EXPOSURE AND TOXICITY: DMDM Hydantoin is a formaldehyde releaser, which means that the substance can release a formaldehyde. Formaldehyde is classified as carcinogenic and allergenic. A 1-year study was conducted to examine the frequency of sensitization to a series of 13 common preservatives. A group of 2,295 consecutive outpatients with suspected allergic contact dermatitis was tested in this study. The rates of positive reactions to the preservatives studied are as follows: formaldehyde 5.7%, and DMDM hydantoin 1.7%. DMDH hydantoin also causes irreversible eye damage. ANIMAL STUDIES: From the dermal study in rabbits it was concluded that the test material was practically nonirritating to the skins of rabbits receiving the 0.008 g/kg dose and mildly to moderately irritating to those receiving the 0.8 g/kg dose. In a developmental study a 55% DMDM Hydantoin solution was administered orally via gavage to rabbits. Only one test substance-related death was reported. There were no significant differences between control (positive and negative) and experimental groups concerning the incidence of necropsy findings. The results of external and skeletal fetal examinations were not significantly different between negative control and experimental groups. The test substance did not induce strand breaks or cross-links in rat testicular DNA after oral administration to rats. A 55% DMDM Hydantoin solution was tested in the Salmonella/mammalian-microsome preincubation mutagenicity assay using the following strains of S. typhimurium with and without metabolic activation: TA-98, TA-100, TA-1535, TA-1537, and TA-1538. A positive response (3.2 fold increase in average number of revertants) was noted for strain TA-98, without metabolic activation; with metabolic activation, a 1.9-fold increase was noted. Additionally, increases of 2.2-fold and 1.7-fold were noted for strain TA-100 with and without activation, respectively. A 55% DMDM Hydantoin solution was tested in the L5178Y TK+/- mouse lymphoma assay, with and without metabolic activation. Under the conditions of testing, the test substance caused a significant dose-dependent increase in the mutant frequency of cultures treated in both the presence and absence of metabolic activation.
LD50 Sprague-Dawley Rat (male) oral 3-5 g/kg|LD50 Sprague-Dawley Rat (female) oral; 2.0-3.65 g/kg|LD50 Rat oral 3.72 +/- 0.5 g/kg
1,3-Dimethylol-5,5-dimethylhydantoin's production and use as an antimicrobial in adhesives, air fresheners, caulking compounds, clay slurries, cleansers, coatings, dispersed colors, resin emulsions, fabric softeners, hydraulic fluids, inks, latex, liquid detergents, metal working cutting fluids, paints (emulsion, latex, water-based), paper/paperboard coatings, polishes, polymers (synthetic), powdered detergents, sealants, carpet shampoos, soap, stains (preservative incorporation), starch solutions, textiles, and wax(1) may result in its release to the environment through various waste streams(SRC). Its use in numerous household products, such as antibacterial hand soaps, shampoos, moisturizing creams, body washes, conditioners, hair care products(2) and its use as an inert ingredient in pesticide formulations(3) will result in its direct release to the environment(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), a measured Koc value of <17.8(2) indicates that 1,3-dimethylol-5,5-dimethylhydantoin is expected to have very high mobility in soil(SRC). Volatilization of 1,3-dimethylol-5,5-dimethylhydantoin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.9X10-14 atm-cu m/mole(SRC), derived from its vapor pressure, 9.0X10-8 mm Hg(2), and water solubility, 7.73X10+5 mg/L(3). 1,3-Dimethylol-5,5-dimethylhydantoin is not expected to volatilize from dry soil surfaces based upon its vapor pressure(SRC). 1,3-Dimethylol-5,5-dimethylhydantoin was found to be readily biodegradable using OECD Guideline 301 A (Ready Biodegradability: DOC Die Away Test) with 75% degradation in 10 days and 95% degradation in 28 days(2). 1,3-Dimethylol-5,5-dimethylhydantoin is susceptible to aqueous hydrolysis with half-lives of <1 day at pH 7 and pH 9(2); no hydrolysis occurs at pH 4(2). This suggests that abiotic hydrolysis may be an important fate process in neutral or alkaline soils(SRC).|AQUATIC FATE: Based on a classification scheme(1), a measured Koc value of <17.8(2), indicates that 1,3-dimethylol-5,5-dimethylhydantoin is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.9X10-14 atm-cu m/mole(SRC), derived from its vapor pressure, 9.0X10-8 mm Hg(3), and water solubility, 7.73X10+5 mg/L(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from a log Kow of -2.9(3) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 1,3-Dimethylol-5,5-dimethylhydantoin was found to be readily biodegradable using OECD Guideline 301 A (Ready Biodegradability: DOC Die Away Test) with 75% degradation in 10 days and 95% degradation in 28 days(3). Aqueous hydrolysis tests conducted pH 4, pH 7 and pH 9, determined respective hydrolysis half-lives of >1 year, <1 day and < 1 day at 25 °C(3) suggesting that hydrolysis is an important fate process in neutral and alkaline waters(SRC). 5,5-Dimethylhydantoin and formaldehyde were identified as the hydrolysis products(3).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,3-dimethylol-5,5-dimethylhydantoin, which has a vapor pressure of 9X10-8 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 1,3-dimethylol-5,5-dimethylhydantoin is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 13 hours(SRC), calculated from its rate constant of 3.0X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 1,3-dimethylol-5,5-dimethylhydantoin may be removed from the air by wet or dry deposition(SRC). Based on direct photolysis tests with 5,5-dimethylhydantoin(2), 1,3-dimethylol-5,5-dimethylhydantoin does not contain chromophores that absorb at wavelengths >290 nm and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of 1,3-dimethylol-5,5-dimethylhydantoin with photochemically-produced hydroxyl radicals has been estimated as 3.0X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 13 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Aqueous hydrolysis tests conducted pH 4, pH 7 and pH 9, determined respective hydrolysis half-lives of >1 year, <1 day and < 1 day at 25 °C(2). A 2009 hydrolysis study using OECD Guideline 111 (Hydrolysis as a Function of pH) at 35 °C, determined half-lives of 10.7 hours and <1 hour at respective pH's of 7 and 9(2); no hydrolysis was observed at pH 4(2); 5,5-dimethylhydantoin and formaldehyde were identified as the hydrolysis products(2). Using EPA Guideline Subdivision N 161-2 (Photodegradation Studies in Water), aqueous solutions of 5,5-dimethylhydantoin were exposed to a Xenon lamp at wavelengths >290 nm for 30 days and pH 6.88-7.12(2); the direct photolysis half-life was approximated to be 878 days(2). This suggests that the structurally similar 1,3-dimethylol-5,5-dimethylhydantoin (in terms of chromophores that absorb at wavelengths >290 nm) is not expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 3 was calculated in fish for 1,3-dimethylol-5,5-dimethylhydantoin(SRC), using a log Kow of -2.9(1) and a regression-derived equation(2). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). Dimethylhydantoin (DMT), a degradation product of 1,3-dimethylol-5,5-dimethylhydantoin, has a BCF of 0.08(1).
Using OECD Guideline 121 (Estimation of the Adsorption Coefficient (Koc) on Soil and on Sewage Sludge using High Performance Liquid Chromatography (HPLC)), the Koc of 1,3-dimethylol-5,5-dimethylhydantoin was determined to be <17.8(1). According to a classification scheme(2), this estimated Koc value suggests that 1,3-dimethylol-5,5-dimethylhydantoin is expected to have very high mobility in soil.
The Henry's Law constant for 1,3-dimethylol-5,5-dimethylhydantoin is estimated as 2.9X10-14 atm-cu m/mole(SRC) derived from its vapor pressure, 9.0X10-8 mm Hg(1), and water solubility, 7.73X10+5 mg/L(2). This Henry's Law constant indicates that 1,3-dimethylol-5,5-dimethylhydantoin is expected to be essentially nonvolatile from water surfaces(3). 1,3-Dimethylol-5,5-dimethylhydantoin's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). 1,3-Dimethylol-5,5-dimethylhydantoin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure.
According to the 2012 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of 1,3-dimethylol-5,5-dimethylhydantoin is 50-99; the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 88,285 workers (67,234 of these are female) are potentially exposed to 1,3-dimethylol-5,5-dimethylhydantoin in the US(1). The NOES Survey does not include farm workers. Occupational exposure to 1,3-dimethylol-5,5-dimethylhydantoin may occur through inhalation and dermal contact with this compound at workplaces where 1,3-dimethylol-5,5-dimethylhydantoin is produced or used. Use data indicate that the general population may be exposed to 1,3-dimethylol-5,5-dimethylhydantoin via dermal contact with consumer products, such as shampoos, hand sanitizers and other household products(2), containing 1,3-dimethylol-5,5-dimethylhydantoin(SRC). The general population may be exposed to 1,3-dimethylol-5,5-dimethylhydantoin via ingestion of foods as a result of indirect food uses that include paper and adhesives used to package food products(3).|Cosmetic products containing DMDM Hydantoin are applied to the skin and hair and may come in contact with the eyes, nasal mucosa, and other parts of the body ... Product formulations containing DMDM Hydantoin may be applied as often as several times daily. Many of the products may be expected to remain in contact with the skin for as briefly as 15 to 30 minutes and may be used repeatedly over a period of several years(1).|Data provided by FDA in 2002 indicated that DMDM Hydantoin was being used in 963 cosmetic products. Current use concentration data indicate slightly lower maximum use concentration of 0.8%, compared to the 1% maximum use concentration that was reported in 1981 ... patch test results for DMDM Hydantoin in large populations of patients with suspected allergic contact dermatits indicated that the frequency of allergic reactions to DMDM Hydantoin has not increased over time(1).
Drug Information
A 0.1 mL aqueous solution containing 0.1 mCi of 1,3-dihydroxymethyl-5,5'-dimethylhydantoin-5-(14)-C was applied to the middorsal area of young adult male Sprague-Dawley rats. After 72 hours, more than 90% of the applied dose was recovered; more than 98% of the recovered activity was confined to the dose site. At the time of killing, less than 1% of the radioactivity was distributed in all body tissues. The higher counts of radioactivity were reported for the gastrointestinal tract, liver, and bone marrow. For most tissue samples, there was no evidence of accumulation of DMDM Hydantoin or its metabolites. DMDM Hydantoin and its metabolites are excreted primarily via the urine. The amount of (14)C activity in the urine decreased approximately 6 times over a 72-hour period; radioactivity in the feces remained approximately constant and significantly below that of the urine.
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
/HUMAN EXPOSURE STUDIES/ From April 2001 to December 2002, a group of 514 patients (178 men, 336 women, average age 42.8 years) suffering from chronic eczema were tested by means of epicutaneous tests for contact hypersensitivity to selected auxiliary substances of dermatological external and cosmetic preparations. In 194 patients, the principal diagnosis was atopic eczema. Of the preservatives, the most frequently sensitizing agents were thiomersal in 13.6%, phenylmercuric acetate in 7.8%, formaldehyde in 5.6%, bronopol in 5.1%, chlorohexidine in 3.3%, dibromodicyanobutane/phenoxyethanol in 2.9%, chloroacetamide in 2.1%, Kathon CG and parabenes in 1.9%, imidazolidinyl urea and diazolidinyl urea in 1.4%, glutaraldehyde in 1.2%, DMDM-hydantoin in 1.0%, dichlorophen in 0.8%, sorbic acid, phenoxyethanol and triclosan in 0.6%, benzalkonium chloride, Quaternium-15 and chlorocresol in 0.4% and chloroquinaldol in 0.2% of the group of patients. Of antioxidizing agents, it was dodecyl gallate in 2.3%, butylhydroxyanisol in 1.2%, propyl gallate in 0.6%, butylhydroxytoluen in 0.4% of the group of patients and of emulsifiers, alcohols lanae in 5.1%, triethanolamine in 1.6% and propylene glycol in 0.4% of the group of patients.|/HUMAN EXPOSURE STUDIES/ ... 35 formaldehyde-allergic patients were patch tested with serial dilutions of formaldehyde (0.1%-0.3%-1.0% aq.) and DM hydantoin (the non-formaldehyde-containing parent compound of DMDM hydantoin). 21 were also patch tested with MDM hydantoin (1 molecule formaldehyde) in serial dilutions: 7 (33%) reacted to 1 or more concentrations. The other 14 were also tested with DMDM hydantoin (2 molecules formaldehyde) in serial dilutions: 8 (57%) reacted to 1 or more concentrations. Patients patch-test-positive to formaldehyde 0.1% and/or 0.3% tended to show more patch test reactivity to DMDM hydantoin than those who reacted only to 1%. Aqueous solutions of DMDM hydantoin in concentrations as used in cosmetic products therefore contain enough free formaldehyde to cause dermatitis in a patch test system in some formaldehyde-allergic patients: 12 such patients applied a cream containing 1% DMDM hydantoin to the flexor aspect of the lower arm twice daily for 1 week; 4 (33%) developed dermatitis. The use of a cream containing 0.25% DMDM hydantoin in these 4 patients still caused dermatitis in 1 and provoked itching in another.|/HUMAN EXPOSURE STUDIES/ Results of patch testing with standard screening allergens (32 chemicals) in 1199 patients, 19 vehicle and preservative allergens in 707 patients, and 10 special studies allergens in 613 patients by 10 dermatologists of the North American Contact Dermatitis Group (NACDG) over a 4 month period are presented. The most common standard allergens were, in order of frequency, nickel, p-phenylenediamine, quaternium-15, neomycin, thimerosal, formaldehyde, cinnamic aldehyde, ethylenediamine, chromate, and thiuram mix. The most common vehicle and preservative allergens were ammoniated mercury, 2-bromo-2-nitropropane-1,3-diol (Bronopol), diazolidinyl urea, captan, chloxylenol, and DMDM hydantoin. There were few (7/661, 1.06%) paraben mix reactions in spite of the attention they have received as potential sensitizers.|/EPIDEMIOLOGY STUDIES/ From February 1989 to January 1990, the Swiss Contact Dermatitis Research Group conducted a 1-year study to examine the frequency of sensitization to a series of 13 common preservatives. A group of 2,295 consecutive outpatients with suspected allergic contact dermatitis (age range 7-90 years, with a mean age of 42; 911 males, 1384 females) was tested. The %s of positive reactions to the preservatives studied are as follows, in descending order: formaldehyde 5.7%, benzalkonium chloride 5.5%, Kathon CG 5.5%, thimerosal 4.2%, chlorhexidine digluconate 2.0%, DMDM hydantoin 1.7%, paraben mix 1.7%, chloroacetamide 1.5%, Bronopol 1.2%, imidazolidinyl urea 1.0%, quaternium 15 1.0%, triclosan 0.8%, 2,4-dichlorobenzyl alcohol 0.4%.|For more Human Toxicity Excerpts (Complete) data for 1,3-DIMETHYLOL-5,5-DIMETHYLHYDANTOIN (6 total), please visit the HSDB record page.
1,3-dimethylol-5,5-dimethylhydantoin
DMDM Hydantoin Use and Manufacturing
DMDM Hydantoin is produced by reacting 3 to 5 moles of formaldehyde, as the 37% by weight aqueous solution, with 1 mole of dimethylhydantoin at 84 °C. A highly concentrated aqueous solution of the compound is prepared by reacting 2 moles of formaldehyde, as 37% formalin, with dimethylhydantoin at 38 to 50 °C, pH 8.1 to 8.3.
Glydant(R) 2000 is an effective cosmetic preservative. Product Data Sheet
Intermediates
Building/construction materials not covered elsewhere
1,000,000 - 10,000,000 lb|This chemical is listed as an Extended High Production Volume (EHPV). Chemicals listed as EHPV were produced in or imported into the U.S. in >1 million pounds according to the 2002 Toxic Substances Control Act (TSCA) Inventory Update. The EHPV program is a voluntary initiative that allows companies to demonstrate that adequate screening data exist for organic HPV chemicals.|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7156]|Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 2,4-Imidazolidinedione, 1,3-bis(hydroxymethyl)-5,5-dimethyl-. Aggregated National Production Volume: 1 to < 10 million pounds.|Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 2,4-Imidazolidinedione, 1,3-bis(hydroxymethyl)-5,5-dimethyl-. National Production Volume: Withheld.
It is available in solid and in aqueous solution forms, including low free formaldehyde versions of the latter.|Troysan 680 (Troy Chemical Corporation): Active ingredient: 1,2-benzisothiazolin-3-one 10.9%; 2,4-Imidazolidinedione, 1,3-bis(hydroxymethyl)-5,5-dimethyl- 12.5%; 2,4-Imidazolidinedione, 1-(hydroxymethyl)-5,5-dimethyl- 2.9%.|Glycoserve LAD (Lonza Inc.): Active ingredient: 2,4-imidazolidinedione, 1,3-bis(hydroxymethyl)-5,5-dimethyl- 45.0%; 2,4-imidazolidinedione, 1-(hydroxymethyl)-5,5-dimethyl- 10.0%.|Glycoserve (Lonza Inc.): Active ingredient: 2,4-imidazolidinedione, 1,3-bis(hydroxymethyl)-5,5-dimethyl- 45.0%; 2,4-imidazolidinedione, 1-(hydroxymethyl)-5,5-dimethyl- 10.0%.|For more Formulations/Preparations (Complete) data for 1,3-DIMETHYLOL-5,5-DIMETHYLHYDANTOIN (17 total), please visit the HSDB record page.
All other basic organic chemical manufacturing|2,4-Imidazolidinedione, 1,3-bis(hydroxymethyl)-5,5-dimethyl-: ACTIVE|The composition of DMDM Hydantoin as determined by gas chromatography is as follows: 94-98% DMDM hydantoin, 2.5-3.0% monomethyloldimethylhydantoin, and other dimethylhydantoin formaldehyde products comprise the balance.|Supplied as a 55.0% solution|Dantogard XL-1000 should be added to the formulation to be preserved at a rate of 1.0 to 10.0 lbs per 1,000 lbs or 0.1% to 1.0% or 1,000 to 10,000 pp based upon the total weight of the product to be protected. If ... articles have been treated with Dantogard XL-1000, do not use them as components in materials used in food packaging and food-holding.|DMDM hydantoin
Analyte: 1,3-dimethylol-5,5-dimethylhydantoin; matrix: personal cleansing product; procedure: high-performance liquid chromatography
DMDM hydantoin has been identified via the following techniques: gas chromatography, infrared spectroscopy, ultraviolet spectroscopy, nuclear magnetic spectroscopy, and differential scanning calorimetry.
Cosmetics -> Preservative
Computed Properties
Molecular Weight:188.18
XLogP3:-0.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:188.07970687
Monoisotopic Mass:188.07970687
Topological Polar Surface Area:81.1
Heavy Atom Count:13
Complexity:251
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Formaldehyde-releasing preservative used to prevent microbial growth in cosmetic products
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