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DMDM 하이단토인

DMDM hydantoin

HCID 22947
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
6440-58-0
표준 SMILES
CC1(C)C(=O)N(CO)C(=O)N1CO
InChIKey
WSDISUOETYTPRL-UHFFFAOYSA-N
분자식
C7H12N2O4
평균 분자량
188.18 g/mol
단동위원소 질량
188.07970687

개요

1,3-Dimethylol-5,5-dimethylhydantoin (DMDM hydantoin) is an antimicrobial formaldehyde releaser preservative with the trade name Glydant. DMDM hydantoin is an organic compound belonging a class of compounds known as hydantoins. It is used in the cosmetics industry and found in products like shampoos, hair conditioners and skin care products. (L1896)

이름 및 식별자

우선 이름
DMDM hydantoin
IUPAC
1,3-bis(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione
현지명
DMDM 하이단토인
영어명
Dimethyloldimethyl hydantoin
분자식
C7H12N2O4
분자량
188.18

이름 및 동의어

6440-58-0DMDM HydantoinDmdmhGlydant1,3-Bis(hydroxymethyl)-5,5-dimethylhydantoin1,3-Dimethylol-5,5-dimethylhydantoinDantoin-DMDMHGlycoserve-DMDMHDantoin dmdmh 55Dimethylol-5,5-dimethylhydantoinDmdmh 552,4-Imidazolidinedione, 1,3-bis(hydroxymethyl)-5,5-dimethyl-
이름 더 보기
DMDM하이단토인DMDM하이단토인(DMDMHYDANTOIN)디엠디엠하이단토인1,3-bis(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dionedimethylolNipaguard DMDMH1,3-bis5-diMethylhydantoin1,3-dimethylol-5,5-dimethyl hydantoin1,3-DIHYDROXYLMETHYL-5,5-DIMETHYLHYDANTOIN
DTXSID80352171,3-Bis(hydroxymethyl)-5,5-dimethyl-2,4-imidazolidinedioneBYR0546TOWDTXCID60152171,3-Di(hydroxymethyl)-5,5-dimethylhydantoin1,3-DIMETHYLOL-5,5-DIMETHYL-HYDANTOINDDAC0.15%Hydantoin, 1,3-bis(hydroxymethyl)-5,5-dimethyl-

데이터베이스 식별자

CAS

물성

구조 계산 물성

XLogP
-0.2
극성 표면적
81.1 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
4
회전 가능 결합 수
2
무거운 원자 수
13
형식 전하
0
복잡도
251

실험 및 물리화학적 성질

Chemical ClassesOther Uses -> Biocides/Disinfectants
Cosmetics · 2건

Cosmetic ingredients (DMDM Hydantoin) -> CIR (Cosmetic Ingredient Review)

Preservative

LogPlog Kow = -2.9
OdorOdorless
Density0.4 g/cu cm at 21 °C /OECD Guideline 109/
Color/Form · 2건

Solid

Powder

Solubility · 2건

In water, 77.3 g/100 cc

In ethanol, 56.4 g/100 cc; in hexane, 0.02 g/100 cc

Boiling Point198-200 °C, decomposes with boiling
Melting Point · 2건

90 °C /OECD Guideline 102/

MP: 102-104 °C /Technical/

Vapor Pressure · 2건

0.00000009 [mmHg]

9.0X10-8 mm Hg at 25 °C

Surface Tension72.4 mN/m at 20 °C /0.998 g/L solution/

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

This chemical does not meet GHS hazard criteria for 11.3% (83 of 737) of reports.

Danger

H302 (67.4%): Harmful if swallowed [Warning Acute toxicity, oral]

P233, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 737 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Not Classified

유해성 정보

Regulatory Information · 4건

Chemical: 2,4-Imidazolidinedione, 1,3-bis(hydroxymethyl)-5,5-dimethyl-

2,4-Imidazolidinedione, 1,3-bis(hydroxymethyl)-5,5-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2,4-Imidazolidinedione, 1,3-bis(hydroxymethyl)-5,5-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: 1,3-bis(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione (EC: 229-222-8)

Hydantoin: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Hydroxymethylated imidazolidinones
Hazards Summary · 1건

A formaldehyde releaser used in cosmetics; It can cause allergic contact dermatitis; Rinse off products in general will have a low risk of causing allergic contact dermatitis. [Kanerva, p. 398-404] Reports of positive results for skin sensitization patch testing; [HSDB] A formaldehyde releasing agent present in combination with MDM hydantoin (CAS# 116-25-6) in the commercial product 2,4 Imidazolidinedione; Likely hydrolyzes/degrades to 5,5-dimethylhydantoin (DMH); [Reference #1] See 5,5-Dimethylhydantoin and Formaldehyde.

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

Formaldehyde may be absorbed following inhalation, oral, or dermal exposure. It is an essential metabolic intermediate in all cells and is produced during the normal metabolism of serine, glycine, methionine, and choline and also by the demethylation of N-, S-, and O-methyl compounds. Exogenous formaldehyde is metabolized to formate by the enzyme formaldehyde dehydrogenase at the initial site of contact. After oxidation of formaldehyde to formate, the carbon atom is further oxidized to carbon dioxide or incorporated into purines, thymidine, and amino acids via tetrahydrofolatedependent one-carbon biosynthetic pathways. Formaldehyde is not stored in the body and is excreted in the urine (primarily as formic acid), incorporated into other cellular molecules, or exhaled as carbon dioxide. (L962)

Absorption, Distribution and Excretion · 1건

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.

용도 및 제조

Uses · 6건

CIR ingredient: DMDM Hydantoin

Used as a biocide in cosmetics with 0.6% the maximum allowable concentration in the EU; [Kanerva, p. 398, 407] Used as an antimicrobial pesticide in cleaning products, adhesives, air fresheners, caulks, hydraulic fluids, inks, metal working cutting fluids, paints, stains, coatings, paper and paperboard coatings, polishes, synthetic polymers, sealants, starch solutions, resin emulsions, textiles, and wax; [Reference #1]

관련 반응

4건
반응 기록 만들기
HRID 1654099 반응식
HRID 1654099반응물로uspto-grants-1995_04
HRID 1654100 반응식
HRID 1654100반응물로uspto-grants-1995_04
HRID 1656130 반응식
HRID 1656130반응물로uspto-grants-1993_10
HRID 1656131 반응식
HRID 1656131생성물로uspto-grants-1993_10

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
6440-58-0
PubChem CID
22947
DTXSID
DTXSID8035217
UNII
BYR0546TOW
EC Number
229-222-8、938-621-2
Nikkaji
J207.046D
Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR

물리화학적 성질

녹는점
1 · 1.00-2.5 °C
끓는 점
303.7 · 303.7±52.0 °C(Predicted)
밀도
1.349 · 1.349±0.06 g/cm3(Predicted)
증기압
0 Pa · 0Pa at 25℃
저장 조건
Sealed in dry,Room Temperature
용해도
DMSO(약간 용해됨), 메탄올(약간 용해됨)
산도 계수 (pKa)
13.41 · 13.41±0.10(Predicted)
물리적 상태
고체
색상
흰색에서 황백색까지
수용성
140 g/L · 140g/L at 20℃
Henry's Law Constant
1.4 · 1.4×106 mol/(m3Pa) at 25℃, HSDB (2015)
안정성
DMSO 솔루션이 불안정함
주요 응용
의약품(소분자)
화장품 원료 기능
항균 방부제
InChI
InChI=1S/C7H12N2O4/c1-7(2)5(12)8(3-10)6(13)9(7)4-11/h10-11H,3-4H2,1-2H3
InChIKey
WSDISUOETYTPRL-UHFFFAOYSA-N
SMILES
C1(=O)N(CO)C(C)(C)C(=O)N1CO
LogP
-2.9 at · -2.9 at 20℃
EPA
1 · 1,3-Dimethylol-5,5-dimethylhydantoin (6440-58-0)

화학적 성질

Liquid

Special ReportsCosmetic Ingredient Review Panel; Final Report on the Safety Assessment of DMDM Hydantoin. J Am Coll Toxicol 7 (3): 245-77 (1988)
FIFRA Requirements · 1건

New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 115501; Type of Pesticide: antimicrobial, fungicide; Use Site: non-food use, household, commercial, industrial use; Year: 1987.

Hazard Classes and Categories · 3건

Acute Tox. 4 (67.4%)

Not Classified

Eye irritation - category 2A

안전 및 보호

Storage Conditions · 2건

Keep container closed. Store in a dry place. Do not store at elevated temperatures. Keep from freezing. Do not reuse empty container. /Dantogard XL-1000/

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.

Cleanup Methods · 2건

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.

Disposal Methods · 5건

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.

Preventive Measures · 4건

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.

Personal Protective Equipment (PPE) · 1건

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/

독성 정보

Health EffectsDMDM hydantoin releases formaldehyde, a known human carcinogen. (L962, L1896)
Ecotoxicity Values · 5건

LC50; Species: Anas platyrhynchos (Mallard duck) age 10-15 days; diet >5000 ppm for 8 days

LD50; Species: Anas platyrhynchos (Mallard duck) oral >1470 mg/kg

LC50; Species: Colinus virginianus (Northern bobwhite) diet >5000 ppm for 8 days

EC50; Species: Daphnia magna (Water flea) age <24 hr; Conditions: freshwater; static; Concentration: 37 ppm for 96 hr (95% confidence interval: 27-51 ppm); Effect: intoxication, immobilization /55% purity/

For more Ecotoxicity Values (Complete) data for 1,3-DIMETHYLOL-5,5-DIMETHYLHYDANTOIN (6 total), please visit the HSDB record page.

Environmental Fate · 3건

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).

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Exposure RoutesOral (L962) ; inhalation (L962) ; dermal (L962)
Toxicity Summary · 3건

Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org

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.

DMDM hydantoin is a formaldehyde releaser. It is likely that formaldehyde toxicity occurs when intracellular levels saturate formaldehyde dehydrogenase activity, allowing the unmetabolized intact molecule to exert its effects. Formaldehyde is known to form cross links between protein and DNA and undergo metabolic incorporation into macromolecules (DNA, RNA, and proteins). (L962, L1896)

Signs and SymptomsDMDM hydantoin may cause contact dermatitis. (A2882)
Soil Adsorption/Mobility · 1건

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.

Human Toxicity Excerpts · 5건

/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.

Artificial Pollution Sources · 1건

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).

Environmental Biodegradation · 1건

AEROBIC: Using OECD Guideline 301 A (new version) (Ready Biodegradability: DOC Die Away Test), 1,3-dimethylol-5,5-dimethylhydantoin was found to be readily biodegradable in activated sludge with 75% degradation in 10 days and 95% degradation in 28 days(1). The degradation product of 1,3-dimethylol-5,5-dimethylhydantoin, 5,5-dimethylhydantoin, was found to be readily biodegradable via OECD Guideline 301 B (Ready Biodegradability: CO2 Evolution Test) with 87% CO2 evolution within 28 days of incubation and >60% degradation in 10 days(1). 5,5-Dimethylhydantoin was steadily biodegraded using OECD Guideline 308 (Aerobic and Anaerobic Transformation in Aquatic Sediment Systems) with half-lives of 13-24 days(1).

Carcinogen Classification1, carcinogenic to humans (for formaldehyde). (L135)

규제 정보

FIFRA Requirements · 1건

New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 115501; Type of Pesticide: antimicrobial, fungicide; Use Site: non-food use, household, commercial, industrial use; Year: 1987.

안전 데이터

wgk
WGK 3
tsca
TSCA listed
HS 번호
29339900
risk_code
22-36-43
hazard_code
Xi,Xn
safety_code
26-36/37
기존화학 물질
KE-03214
Hazard Classifications
Eye Irrit. 2Resp. Sens. 1
스토리지 클래스
10 - Combustible liquids
유해 물질 데이터
6440-58-0(Hazardous Substances Data)

Metal Machining [Category: Heat or Machine]

For 1,3-dimethylol-5,5-dimethylhydantoin (USEPA/OPP Pesticide Code: 115501) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

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.

DMDM Hydantoin is a preservative which is used in cosmetic products at concentrations up to 1%. This ingredient is a formaldehyde donor containing up to 2% of the free aldehyde in equilibrium with the hydantoin.

U.S. Production · 5건

2023: 1,275,131 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#7145]

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.

Consumer UsesPreservative
Industry UsesIntermediate
Methods of Manufacturing · 1건

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.

Formulations/Preparations · 5건

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.

Household ProductsInformation on 803 consumer products that contain DMDM hydantoin in the following categories is provided:
Use ClassificationCosmetics -> Preservative
General Manufacturing Information · 6건

All Other Chemical Product and Preparation 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

응용 분야

용도Dimethyloldimethyl hydantoin is used as preservative in a broad number of household and industrial cleaners to prevent spoilage from microorganisms

공급사100 곳

北京华美互利生物化工010-56205725 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
武汉欣扬瑞和化学科技有限公司13720274133 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
河北展药生物科技有限公司15369953316 +8615369953316 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]
Syntechem Co.,Ltd[email protected]
上海晶抗生物工程有限公司021-54721350 13524668266 · [email protected]
太原市瑞和丰科贸有限公司+86 351 7031519 · [email protected]
石家庄斯迪亚诺精细化工有限公司0311-89250318 13582355795 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
山东洛克化工有限公司17653113209 13065062079 · [email protected]
上海相辉医药科技有限公司13761987713 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
江苏省太仓市严林化工厂0512-53410118 13776174836 · [email protected]
医恩医疗系统研发(上海)有限公司021-58958002 18930822973 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
Xiamen AmoyChem Co., Ltd+86-86-5926051114 · [email protected]
Connect Chemicals GmbH+49 2102 2077 19 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
武汉普洛夫生物科技有限公司17612776928 · [email protected]
深圳菲斯生物科技有限公司0755-83725350 13380397412 · [email protected]
安徽科迪达化工有限公司0554-2106669 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
湖南华腾制药有限公司400-8592883 15367835770 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
江苏艾康生物医药研发有限公司025-66028182 17714375163 · [email protected]
上海彤源化工有限公司021-021-69182866 13701855675 · [email protected]
上海容立化学科技有限公司021-69992220 13701886816 · [email protected]
上海康拓化工有限公司021-69185552 13701777608 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
桦特昇生物科技(武汉)有限公司027-59207879 1972026995 18140587686 · [email protected]
上海波以尔化工有限公司021-50182298 021-50180596 · [email protected]
Henan Alfa Chemical Co., Ltd+8618339805032 · [email protected]
厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]
山东智尚新材料有限公司+8617653113209 · [email protected]
湖北辰心化工有限公司17362916295 · [email protected]
南京择优新材料科技有限公司173-40521416 17340521416 · [email protected]
上海西格生物科技有限公司021-57810052 18930344717 · [email protected]
湖北阡陌生物科技有限公司0711-3812399 18062309155 · [email protected]
武汉克米克生物医药技术有限公司027-13163388153 13163388153 · [email protected]
山东西亚化学有限公司4009903999 13395398332 · [email protected]
安泰精细化工技术有限公司18503026267 · [email protected]

/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.