N-(ヒドロキシメチル)アクリルアミド

less than 1 mg/mL at 68.9 °F (NTP, 1992)

Solubility in water, g/100ml at 20 °C: 188 (very soluble)

165 to 167 °F (NTP, 1992)

75 °C

0.000205 [mmHg]

Vapor pressure, Pa at 25 °C: 0.03 (negligible)

N-methylolacrylamide appears as a colorless or yellow aqueous solution.

Liquid

A colorless or yellow liquid; [CAMEO] White solid; [ICSC] Liquid; [MSDSonline]

WHITE CRYSTALS.

Danger

H340: May cause genetic defects [Danger Germ cell mutagenicity]

P203, P260, P264, P270, P280, P318, P319, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 1.8% (9 of 513) of reports.

Danger

H301 (51.1%): Toxic if swallowed [Danger Acute toxicity, oral]

Chemical: 2-Propenamide, N-(hydroxymethyl)-

Hazard Traits - Carcinogenicity; Genotoxicity

2-Propenamide, N-(hydroxymethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenamide, N-(hydroxymethyl)- 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)

Status: Active Update: 26-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15038

Substance: N-(hydroxymethyl)acrylamide

2-Propenamide, N-(hydroxymethyl)-: Does not have an individual approval but may be used under an appropriate group standard

Literature sources indicate that this chemical is nonflammable. (NTP, 1992)

Combustible.

AMONG 4 FIBER DRUMS OF THIS CHEMICAL /N-HYDROXYMETHYLACRYLAMIDE/, 2 OF WHICH HAD NEVER BEEN OPENED, EXCESSIVE HEAT, SMOKE, CRACKLING & SMALL FLAME WERE NOTED. VERY SMALL AMOUNTS OF CONTAMINANT ARE BELIEVED TO HAVE CATALYZED THIS POLYMERIZATION REACTION, BUT STORAGE IN EXCESSIVELY HEATED AREAS CAN ALSO START THE REACTION.

May undergo spontaneous combustion in storage.

SYMPTOMS: Symptoms of exposure to this compound include irritation of the eyes, skin, mucous membranes and upper respiratory tract. Compounds of this class cause peripheral neuropathies, paresthesias, weakness in lower limbs and bluish, sweaty cold hands with erythema and peeling of the palms.

A skin, eye, mucous membrane, and respiratory tract irritant; Compounds in this class may cause peripheral neuropathy; Aqueous solution are readily absorbed through the skin; [CAMEO] The substance may have effects on the peripheral nervous system. [ICSC] An irritant; Readily absorbed through skin; Targets liver and lungs in high-dose animal studies; [MSDSonline] See Acrylamide.

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Refer for medical attention .

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance, protective clothing, protective gloves and safety goggles. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. Wash away remainder with plenty of water. Wash away remainder with plenty of water. Then store and dispose of according to local regulations.

Sore throat. Cough.

Redness.

Redness.

See Inhalation.

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=924-42-5]

N-Methylolacrylamide

Group 2B: Possibly carcinogenic to humans

Volume 60: (1994) Some Industrial Chemicals

2022 online

2021

N-Methylolacrylamide

NEUROTOXICITY OF ACRYLAMIDE & RELATED COMPD & ITS EFFECT ON THE TESTIS AFTER REPEATED ORAL DOSES WERE STUDIED IN MICE. N-HYDROXYMETHYLACRYLAMIDE WAS AMONG THOSE COMPOUNDS PRODUCING TESTICULAR ATROPHY. HISTOLOGICAL CHANGES PRODUCED WERE DEGENERATION OF THE EPITHELIAL CELLS OF THE SEMINIFEROUS TUBULES WITH INTERSTITIAL CELLS BEING NORMAL. IT ALSO CAUSED NEUROPATHY AS ASSESSED BY ROTAROD PERFORMANCE TEST.

N-HYDROXYMETHYLACRYLAMIDE AT A CONCN OF 1800 PPM (DAILY INTAKE 27 MG/RAT) FOR 1 WK & THEREAFTER 900 PPM (DAILY INTAKE 18.6 MG/RAT) PRODUCED SLIGHT ATAXIA IN MALE PORTON RATS AFTER 5 WK. OVER THE NEXT 2 WK, IN ADDN TO THE DOSING VIA THE DIET, 4 IP DOSES OF N-HYDROXYMETHYLACRYLAMIDE (50 MG/KG) WERE GIVEN. THE DISABILITY BECAME MODERATE AT 7 WK.

... Conclusions: Under the conditions of these 2 year studies, there was no evidence of carcinogenic activity of N-methylolacrylamide for male or female F344/N rats receiving doses of 6 or 12 mg/kg/day by aqueous gavage. There was clear evidence of carcinogenic activity of N-methylolacrylamide for male B6C3Fl mice, based on increased incidences of neoplasms of the Harderian gland, liver, and lung. There was clear evidence of carcinogenic activity of N-methylolacrylamide for female B6C3Fl mice, based on increased incidences of neoplasms of the Harderian gland, liver, lung, and ovary.

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. 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 ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline 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. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/

... Toxicology and carcinogenesis studies were conducted by administering N-methylolacrylamide (98% pure) in water by gavage to groups of F344/N rats and B6C3Fl mice of each sex for ... 2 yr. ... Two yr studies were conducted by administering 0, 6, or 12 mg/kg N-methylolacrylamide in water by gavage, 5 days/wk for 103 wk, to groups of 50 rats of each sex. Groups of 50 mice of each sex were administered 0, 25, or 50 mg/kg on the same schedule. ... Conclusions: Under the conditions of these 2 year studies, there was no evidence of carcinogenic activity of N-methylolacrylamide for male or female F344/N rats receiving doses of 6 or 12 mg/kg/day by aqueous gavage. There was clear evidence of carcinogenic activity of N-methylolacrylamide for male B6C3Fl mice, based on increased incidences of neoplasms of the Harderian gland, liver, and lung. There was clear evidence of carcinogenic activity of N-methylolacrylamide for female B6C3Fl mice, based on increased incidences of neoplasms of the Harderian gland, liver, lung, and ovary.

N'(Hydroxymethyl)-acrylamide (HACR) was evaluated for reproductive toxicity, neurotoxicity, & dominant lethal effects using a modified Reproductive Assessment by Continuous Breeding (RACB) Protocol in CD-1 (Swiss) mice. ... During the continuous breeding phase, exposure to HACR at doses ranging from 11.1+/-0.57 mg/kg/day in the low-dose group males (60 ppm in water), to 113.4+/-15.86 mg/kg/day in the high-dose group females (360 ppm in water), for 27 wks of cohabitation, significantly affected measures of reproductive competence, including a 26% decr in the number of live pups/litter at 360 ppm & an increased inter-birth interval at all doses. However, the mean number of litters/pair, the proportion of pups born alive, or adjusted live pup weight were not affected. In a modified dominant lethal test. HACR-treated F0 males were mated to nontreated females. Significantly more early resorptions were detected at 180 ppm (/about/ 30-40 mg/kg/day) & higher, & fewer pups were born at 360 ppm (/about/ 80 mg/kg/day), indicating an effect of HACR on male reproduction. However, the crossover mating trial indicated no significant affect of 360 ppm HACR on any indices of fertility or mating & did not clearly indicate the affected sex, even though the number of pups/litter was reduced by 1.5 pups on the avg when sires were HACR treated (control x control, 10.6+/-1.0 vs. HACR male x control female, 9.1+/-0.9). Clinically, no dose-related signs were noted in F0 HACR- treated mice. F0 body weight & feed consumption during the initial weeks of HACR exposure were not adversely affected by treatment. HACR produced only slight changes in grip strength: in forelimbs of females after 12 wks (360 ppm) & 27 wks (180 & 360 ppm) of treatment. Trends towards reduced grip strength were also observed in the hind limbs of females & forelimbs of males after 12 wks of dosing. At necropsy of F0 adults, HACR (360 ppm) caused a 14% decr in testicular weight from controls, a 7% reduction in the total number of spermatids, & a 14% reduction in the concn of epididymal spermatozoa. No other dose-related trends in reproductive or somatic organ or body weights were noted for males & none for females. Estrual cycle characteristics were normal. No treatment-related reproductive, neural, or somatic organ histopathology was observed in either sex. In the second generation (F1) growth phase. HACR at dose levels of > or =60 ppm in water did not adversely affect preweaning growth or survival of the F1 generation. However, after weaning, dose-related decreases in body weight occurred in the face of increased water & feed consumption between 82+/-10 & 110+/-10 days of age in the F1 generation, more so in males than in females. Calculated exposure averaged between 15.6+/-0.61 & 188.8+/-11.3 mg/kg/day for adult F1 males & females at 60 & 360 ppm, respectively. No treatment related clinical signs were noted. In the F1 mating trial, HACR at > or =60 ppm had slight effects on the reproductive competence of the F1 generation. HACR caused a 18%-55% reduction in the number of live F2 pups/litter at > or =60 ppm & reduced dam weight by 5%-9% at > or =60 ppm. HACR clearly decreased forelimb & hind limb grip strength of males & hind limbs of females for Weeks 3-10 at most doses, with the forelimb of females being affected only at Week 10. There were significant treatment affects on male body weight, so that any decreases in reproductive organ weight when adjusted for body size were not significant. The exception was the seminal vesicles at 360 ppm, which were relatively smaller than for controls. Sperm parameters significantly affected by HACR were limited to the epididymal spermatozoa concns at 360 ppm (reduced by 13%): Spermatid counts (/mg of testicular weight) were non-significantly decreased (8%), & testicular histopathology was not markedly different from controls. In F1 females, terminal body weight was not reduced, & HACR had no affect on reproductive organ weight, vaginal cytology, or histopathology. In summary, exposure to HACR in water at dose levels as high as 360 ppm (/about/ 115 mg/kg/day), for up to 27 wks, resulted in moderate reproductive toxicity--decreased pups/litter at 360 ppm in F0 mice & at 60, 180, & 360 ppm in F1 mice, longer inter-litter interval in F0 females at 60, 180, & 360 ppm, & increased postimplantation loss (dominant lethal effect at 180 & 360 ppm) for untreated females mated to F0 males, in the absence of any clear-cut systemic toxicity in F0 mice. F1 mice had lowered body weights & increased liver & kidney/adrenal weight at all doses. Testicular toxicity was present in F0 animals at 360 ppm as indicated by decreased weight. Histopathology was not evident. F1 animals were more susceptible than F0 animals to the neuromuscular effects of HACR at all doses: HACR consistently decreased grip strength in both limbs of both sexes in F1 animals during post-weaning development, as opposed to sporadic effects in the hind limbs & forelimbs of F0 animals: more often in females. Neurotoxicity & litter effects were present in both F0 & F1 animals at doses lower than for currently or previously described testicular effects. The F1 generation, exposed from the time of gametogenesis, was more susceptible to neurotoxic & reproductive effects than were the F0 animals. We were not able to separate reproductive effects from testicular toxicity, although early resorptions occurred at a lower dose (180 ppm) than decreased testicular weight (360 ppm). Testicular effects were observed in F0 males at doses that did not cause neurotoxicity. Thus, these data indicate that HACR does affect reproductive performance of either F0 or F1 mice under the conditions used in Tasks 2-4 of this study (at doses < or =120 mg/kg/day). HACR had dominant lethal effects, which reduced live litter size by 26% in the F0 mice & by as much as 55% for the F1 mice at the high dose. The reduced number of pups/litter was equivalent in pairs fed HACR to those after exposed males were mated to nontreated females in the dominant lethal test. Thus, the dominant lethal effects may account for all of the F0 reproductive toxicity.

LD50 Rat oral 474 mg/kg

LD50 Rat ip 563 mg/kg

LD50 Mouse oral 420 mg/kg

AFTER A DOSE OF 100 MG/KG OF ACRYLAMIDE NO NEUROLOGICAL SIGNS OF NEUROPATHY HAD YET APPEARED, BUT RETROGRADE BUILDUP OF PROTEIN LABEL WAS SIGNIFICANTLY REDUCED FOR THE LONG INTERVAL. TO TEST THE SPECIFICITY OF ACRYLAMIDE ON THE RETROGRADE TRANSPORT DEFECT N-HYROXYMETHYLACRYLAMIDE WAS STUDIED. IT DID NOT INFLUENCE THE TRANSPORT.

N-HYDROXYMETHYLACRYLAMIDE IV INJECTED INTO RATS @ 140 MG/KG WAS DISTRIBUTED THROUGHOUT THE TOTAL BODY WATER WITHIN A FEW MIN. BREAKDOWN OF N-HYDROXYMETHYLACRYLAMIDE TO ACRYLAMIDE WAS NEGLIGIBLE IN VITRO & IN VIVO. IT CAUSED A RAPID DECR IN LIVER GLUTATHIONE IN VIVO & GLUTATHIONE CONJUGATES WERE EXCRETED IN THE BILE.

Used in adhesives, binders, surface coatings, and resins; [ChemIDplus] Used as a starch modifier; [HSDB]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

PROPOSED FOR USE IN SUNSCREEN PREPARATIONS

Reactive comonomer (vinyl acetate, styrene-butadiene resins); starch modifier

Plastics Material and Resin Manufacturing

2-Propenamide, N-(hydroxymethyl)-: ACTIVE