N-methylolacrylamide = NMA

CAS Number: 924-42-5
EC / List no.: 213-103-2
Molecular Weight: 101.10

Usages of N-methylolacrylamide:
N-methylolacrylamide has a double bond conjugated with a carbonyl group and a highly reactive methylol group. 
N-methylolacrylamide is a widely used cross-linking monomer for fiber modification, resin processing, adhesives and paper, leather, metal surfaces The treatment agent can also be used as a soil amendment. 
N-methylolacrylamide can be used as a cross-linking agent widely used in fiber modified resins, processing dyes, plastic adhesives to make emulsion adhesives and thermosetting acrylic coatings; copolymers with acrylamide can be used as waterproofing agents, flame retardants, etc. 
Condensation with cotton fibers can prevent fabric wrinkles and improve stain resistance.

Uses of N-methylolacrylamide:
N-Methylolacrylamide is a bifunctional monomer with reactive vinyl and hydroxyethyl groups. 
Thermoplastic polymers can be formed by copolymerization of N-methylolacrylamide with a variety of vinyl monomers by emulsion, solution and suspension techniques. 
The resulting products, which have pendant hydroxyethyl groups, can undergo cross-linking under moderate conditions, permitting conversion of thermoplastic backbone polymers to thermoset materials at the point of use in the absence of an external cross-linking agent. 
Conversely, the hydroxyethyl group can be reacted with a substrate like cellulose and subsequently cross-linked by free-radical polymerization.
The uses of N-methylolacrylamide range from adhesives and binders in papermaking and textiles to a variety of surface coatings and resins for varnishes, films and sizing agents . 
N-methylolacrylamide can be used in wet-strength and dry-strength agents for paper, in textile finishing agents for crease resistance, in antistatic agents, in dispersing agents, in cross-linking agents and in emulsion polymers.
Chemical intermediate, reactive comonomer; production of polymers for coatings, varnishes, and adhesion; crease resistance in cotton material.
N-methylolacrylamide (NMA) are used in the formulation of grouting materials. 
Acrylamide reacts readily with formaldehyde to form N-methylolacrylamide

Properties of N-methylolacrylamide:
White crystalline powder. 
Melting point: 74-75 oC; 
relative density: 1.074. 
Dissolving in water very easily and having good solubility in hydrophilic solvents such as ethanol, ethyl acetate, acrylic acid or acrylates, etc. but almost undissolving in hydrophobic solvents such as hydrocarbon, halo hydrocarbon, etc.

NMA is a special monomer with two functional groups, they are ethenyl and methylol. 
Through emulsion polymerization or solution polymerization, thermoplastic polymer may be obtained by comining NMA with many kinds of ethenyl monomer. 
Because there are functional groups of methylol in the branch chain, this thermoplastic polymer can self cross-link into cross-linked polymer under certain condition.

Uses of N-methylolacrylamide:
Organic synthetic monomer to produce copolymer, including thermosetting resin, optical curing epoxy resin coating oil-proof coating for canvas, baking coating for automobile, boat & machine. 
N-methylolacrylamides emulsion can be used in the coating and base layer of fabrics, fiber finishing, leather coating, paper coating and spray cotton or used as adhesive

N - Methylolacrylamide (NAM) was prepared from HCHO and acrylamide (AM) in the presece of basic catalyst. 
The optimal reaction conditions were AM: HCHO= 1: 1. 05(moL), pH= 9, temperature 70℃ and reaction time 3~3. 5 h, giving 99% conversion. 
The reaction mixture, NAM aqueous solution approximately, may be directly applied in the preparation of crosslinking polymers as a crosslinking agent.

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

N-Methylolacrylamide is a bi-functional monomer with reactive vinyl and hydroxyethyl groups. 
Thermoplastic polymers can be formed by copolymerization of N-methylol-acrylamide with a variety of vinyl monomers by emulsion, solution and suspension techniques. 
The resulting products, which have pendant hydroxyethyl groups, can undergo cross-linking under moderate conditions, permitting conversion of thermoplastic backbone polymers to thermoset materials at the point of use in the absence of an external cross-linking agent. 
Conversely, the hydroxyethyl group can be reacted with a substrate like cellulose and subsequently cross-linked by free-radical polymerization
The uses of N-methylolacrylamide range from adhesives and binders in papermaking and textiles to a variety of surface coatings and resins for varnishes, films and sizing agents. It can be used in wet-strength and dry-strength agents for paper, in textile finishing agents for crease resistance, in antistatic agents, in dispersing agents, in cross-linking agents and in emulsion polymers.

Chemical Properties:
White solid
General Description:
A colorless or yellow aqueous solution.
Air & Water Reactions:
Soluble in water.
Reactivity Profile:
N-Methylolacrylamide may be sensitive to prolonged exposure to light. 
Polymerization and generation of heat and flames may occur on exposure to to heat or contaminants. 
Incompatible with strong oxidizers.
Fire Hazard:
Literature sources indicate that N-Methylolacrylamide is nonflammable.

How is N-methylolacrylamide useful in textile processing  co-polymers, which are used for a variety of purposes. 
Polyacrylamides are in surface coatings and adhesives, textile dyeing, leather processing, paper and cardboard manufacture and in cosmetics. 
Some countries from the use of acrylamide and N-methylolacrylamide (NMA) grouting agents.

Use Of  N-Methylol Acrylamide:
N-methylolacrylamide is made By Microbiological Method. 
With the characteristics of higher purity and no copper and lower iron content, N-methylolacrylamide is especially suitable for polymer production and uniform molecular weight spread. 
N-methylolacrylamide is mainly used to produce different kinds of homopolymers and modified polymers and also is widely applied to , dyestuff, painting and daily chemicals industries.

N- Methylolacrylamide is not known to occur as a natural product.

Occupational exposure:
No data on human exposure to N-methylolacrylamide were available to the Working Group.

Experimental systems:
After iN-methylolacrylamides intravenous administration at 140 mg/kg bw to rats, N-methylolacrylamide was distributed rapidly in total body water, with a first-order rate of elimination of 0.45/h from the blood compartment. 
Evidence for glutathione conjugation with N-methylolacrylamide in the bile was found in studies with the substance labelled in the methylene carbon, but no evidence was found for conversion to acrylamide in vivo. 
N-methylolacrylamide is not known whether N-methylolacrylamide, like acrylamide, is also converted to an epoxide metabolite. 
No data were available on urinary about N-methylolacrylamide metabolites.

Chem. Abstr. Sem Reg. No.: 924-42-5
Deleted CAS Reg. No.: 90456-67-0
Chem. Abstr. Name: N-(Hydroxymethyl)-2-propenamide
IUPAC Systematic Name: N-(Hydroxyethyl)acrylamide
Synonyms: N-MAM P; N-methanolacrylamide; monomethylolacrylamide; NMA
Boiling Point: 277 °C
Melting Point: 165 to 167 °F (NTP, 1992)
Solubility: less than 1 mg/mL at 68.9° F
Vapor pressure: Pa at 25 °C: 0.03 (negligible)
Melting point:74-75°C
Boiling point:277°C(lit.)
Density 1.082 g/mL at 20 °C
vapor pressure 31 hPa (25 °C)
refractive index n20/D 1.413
Flash point:100°C
storage temp. Refrigerator
Specific Gravity1.074
PH6.0-7.0 (H2O, 20°C)
Water Solubility <0.1 g/100 mL at 20.5 ºC
BRN 506646

Description: White crystalline solid
Melting-point: 74-75 °C
Spectroscopy data: Infrared (10698), ultraviolet and nuclear magnetic resonance spectral data have been reported.
Solubility: Soluble in water (188 g/lOO ml at 20°C), methanol (149 g/lOO ml at 30°C), 90% ethanol (116 g/lOO ml at 30°C), isopropanol (53 g/100 ml at 30°C) and n-butanol (42 g/100 ml at 30°C) (American Cynamid Co., 1990a).
Stability: Aqueous solutions are highly reactive. 

Upon heating in the presence of acids, they are rapidlypolymerized to infusible resins. 
The stability of solutions is dependent mainly upon oxygen level, contaminants, storage tempeIature and pH, if Conversion factor: mg/m3 = 4.13 x ppm
N-methylolacrylamide an added stabilizer or inhibitor can influence the toxicological properties of this substance, consult an expert. 
N-methylolacrylamide is toxic to aquatic organisms. 
N-methylolacrylamide is strongly advised not to let the chemical enter into the environment. 

Routes of exposure:
N-methylolacrylamide can be absorbed into the body by inhalation, through the skin and by ingestion. 

Effects of short-term exposure
N-methylolacrylamide is mildly irritating to the eyes and skin. 
N-methylolacrylamide may cause effects on the nervous system. 

Density: 1.074
Boiling Point: 318.1±34.0 °C at 760 mmHg
Melting Point: 74-75°C
Molecular Formula: C4H7NO2
Molecular Weight: 101.104
Flash Point: 146.2±25.7 °C
Exact Mass: 101.047676
PSA: 49.33000
LogP: -1.48
Vapour Pressure: 0.0±1.5 mmHg at 25°C
Index of Refraction: 1.459
Storage condition: Refrigerator
Water Solubility: <0.1 g/100 mL at 20.5 ºC

Formula: C4H7NO2
Molecular mass: 101.1
Boiling point: 277°C
Melting point: 75°C
Solubility in water, g/100ml at 20°C: 188
Vapour pressure, Pa at 25°C: 0.03 (negligible)
Octanol/water partition coefficient as log Pow: -1.81

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. 
Do NOT let this chemical enter the environment. 
Sweep spilled substance into covered containers. 
Then store and dispose of according to local regulations. 

Air & Water Reactions
Soluble in water.
Fire Hazard
Literature sources indicate that this chemical is nonflammable. (NTP, 1992)
Health Hazard

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.

ACUTE/CHRONIC HAZARDS: The vapor or mist of this compound is irritating to the skin, eyes, mucous membranes and upper respiratory tract. 
In aqueous solution, N-methylolacrylamide is readily absorbed through the skin. 
When heated to decomposition N-methylolacrylamide emits toxic fumes of carbon dioxide, carbon monoxide and nitrogen oxides. 

N-methylolacrylamide either individually or in combination is chemically modified jute is found to improve or alter the important textile related properties like moisture regain, tensile properties, fabric stiffness, crease recovery angle, shrinkage parameters, and thermal behavior, this leads to reduction in warp-way tenacity.
The polymerization and condensation reaction of N-methylolacrylamide within cotton fabrics in which K2S2O8, (NH4) 2S 2O8, or H2O2 can be used as initiator and NH4 Cl or (NH4 )2HPO4 used as the acid condensation catalyst. 
Crease recovery and abrasion resistance (flat) of the treated fabric increased with higher value of resin content; tear strength. 
The effect of the addition of acid catalysts such as NH4Cl on the extent of the crease resistance is considerable, although some marked improvement was obtained in neutral catalysts such as K2S2O8 alone.

Treatment usefulness of N-methylolacrylamide:
The addition of co-monomers such as acrylamide and hexamethylene diamine HCl-salt as well as softeners to the treating bath may be effective in improving the strength losses induced by this treatment. 
Aftertreatment of the N-methylolacrylamide-treated fabric with hexamethylenediamine or thereafter with formalin may be also effective, since somewhat continuous distribution of the different kinds of network-structures within the fiber could be obtained by this procedure.

A method for producing N-methylolacrylamide which comprises reacting acrylamide with formaldehyde or paraformaldehyde in an aqueous solvent in the presence of (A) a basic compound and at least one member selected from the group consisting of a salt of Mo-containing acid and a salt of W-containing acid, or (B) a quaternary ammonium hydroxide compound, is provided by the present invention. 
According to the method of the present invention, N-methylolacrylamide having few by-products is obtained in high yields.

N-Methylolacrylamide uses and applications include: Starch modifier; reactive comonomer for vinyl acetate, SB resins Suggested storage of N-Methylolacrylamide: Light-sensitive

CAS No:924-42-5
Molecular Formula :C4H7NO2
Molecular Mass :101.10400
Exact Mass :101.04800
PSA :49.33000
LogP :-0.37070
EINECS :213-103-2
H-bond Acceptor :2
H-bond Donor :2
RBN :2

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

Density :1.074
Melting Point :74-75ºC
Bolling Point :318.1ºC at 760mmHg
Flash Point :146.2ºC
Refractive Index :n20/D 1.413
Solubility :Solubility in water, g/100ml at 20°C: 188
Storage Condition :Refrigerator
Vapor Pressure :Vapour pressure, Pa at 25°C: 0.03 (negligible)
Stability :May undergo spontaneous combustion in storage.

Safety Information
HS Code :2924199090
UN No. :UN 2810
WGK_Germany :3
Risk Code :R22
Safety Instructions :26
RTECS No. :AS3600000
Dangerous Mark :Xn
Storage :Separated from acids. Store only if stabilized. Store in an area without drain or sewer access.
P Code :P201-P280-P301 + P310 + P330-P333 + P313
Hazard Statements :H301-H317-H340-H350-H361-H372

Scientific Name: N-(Hydroxymethyl)-2-propenamide; N-(Hydroxymethyl)acrylamide
CAS No.: 924-42-5
Model No.: ACH8-03
Molecular Formula: C4H7NO2
Molecular Weight: 101.10

N-Methylolacrylamide Usage:
1. A widely used cross-linking monomer for fiber modification, resin processing, adhesives and paper, leather, metal surface treatment agents, and soil improvers.
2. As an organic synthesis monomer, it can be used to prepare a variety of copolymers.

N-Methylolacrylamide Storage:
Storage in a dark, cool, ventilated, and dry environment

N-Methylol Acrylamide
2-Propenamide, N-(hydroxymethyl)-
Acrylamide, N-(hydroxymethyl)-
N-Hydroxymethyl acrylamide
Uramine T 80
NSC 553
Yuramin T 80
N-(Hydroxymethyl)acrylamide SOLUTION
CCRIS 2380
HSDB 4361
EINECS 213-103-2
BRN 0506646
EC 213-103-2
N-(hydroxymethyl) acrylamide
N-(Hydroxymethyl)acrylamide solution, 48 wt. % in H2O
Rocagil BT
Yuramin T 80
Uramine T 80
Uramine T 80
MH 100
MH 100 (AMIDE)
NMA 60

Appearance: Colorless or Yellow Aqueous Solution
CAS Number: 924-42-5
Chemical Composition: Formaldehyde;Acrylonitrile;Acrylamide
Density: 1.082 g/mL
EINECS Number: 213-103-2
IUPAC Name: N-(Hydroxymethyl)Prop-2-Enamide
Melting Point: 74-75°C
Molar Mass: 101.1 g/mol
Molecular Formula: C4H7NO2
RTECS Number: AS3600000
Refractive: 1.413n20/D
Acrylamide, N-(Hydroxymethyl)-

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

STORAGE PRECAUTIONS: You should protect this material from exposure to light. 
Keep it away from oxidizing materials and store it at refrigerated temperatures. 
Protective Clothing
MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of N-methylolacrylamide, wear disposable Tyvek-type sleeves taped to your gloves.

RECOMMENDED RESPIRATOR: Where N-methylolacrylamide is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter).

Inhalation risk of N-methylolacrylamide:
A harmful concentration of airborne particles of N-methylolacrylamide can be reached quickly when dispersed, especially if powdered. 

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.
SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. 
Gently wash all affected skin areas thoroughly with soap and water. 
IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. 
IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas.
INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. 
IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. 
Provide proper respiratory protection to rescuers entering an unknown atmosphere. 
Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.
If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. 
Be prepared to transport the victim to a hospital if advised by a physician. 
If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. 
IMMEDIATELY transport the victim to a hospital.
OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure.

EC / List no.: 213-103-2
CAS no.: 924-42-5
Mol. formula: C4H7NO2

contains: 30 ppm monomethyl ether hydroquinone as inhibitor
Quality Level: 100
concentration: 48 wt. % in H2O
refractive index: n20/D 1.413
density: 1.074 g/mL at 25 °C
SMILES string: OCNC(=O)C=C
InChI: 1S/C4H7NO2/c1-2-4(7)5-3-6/h2,6H,1,3H2,(H,5,7)

Acrylamide, N-(hydroxymethyl)-
Uramine T 80
Yuramin T 80
NCI-C60333; N-Methyloacrylamide
NSC 553
Acrylamide, N-(hydroxymethyl)-
N-(Hydroxymethyl) acrylamide
Monomethylolacrylamide NMA
2-Propenamide, N-(hydroxymethyl)-

Product group:Acryl- en Methacrylamide + derivatives
Synonym product:n-(hydroxymethyl)acrylamide; NMA
Package:Bulk and Packed Materials
Statistics number:2924-19-00(- )
Cas number:924-42-5
Cus number:N/A
EC number:213-103-2
RID/ADR number:N/A
UN number:N/A

white crystal powder
1.074 g/mL at 25 °C
Melting point:
Boiling point:
318.1 °C at 760 mmHg
Flashing point:
>93 °C
Storage temperature:
Coefficient of refraction:
n20/D 1.413

Several variations of polymerization-crosslinking of N-methylolacrylamide (NMA) in cotton were explored to clarify factors critical to achievement of resilience with superior retentions of strength and abrasion resistance in fabric. 
Per sulfate catalysis simultaneously initiated both polymerization and crosslinking reactions of NMA in cotton fabric; the results from dry-cure reactions fell in the conventional range of textile performance properties achieved by treatment of cotton fabric with agents such as dimethyloldihydroxyethyleneurea. 
Wet-cure reactions carried out in scaled bags at or above 100°C resulted in low resilience, high retentions of strength-abrasion resistance, and large increases in stiffness, the last attributed to fiber bonding in yarns. 
Wet-cure reactions conducted at or below 80°C caused little stiffness, and only in these cases was a subsequent catalyzed dry-cure reaction effective in raising resilience with good retentions of strength and abrasion resistance. 
Inclusion of alkali metal phosphates in the persulfate-initiated reaction of NMA with cotton in a pad-dry-cure caused retentions of abrasion resistance to be very substantially improved and retentions in breaking and tearing strengths to be significantly improved at durable-press appearance ratings of 4.5. 
These results are attributed to relatively sequential but rapid polymerization and crosslinking reactions, to reduction in formation of oxymethylene crosslinks, and possibly to reduced molccular degradation of the cellulose.

Physical state:    A colorless or yellow aqueous solution.
Colour:    no data available
Odour:    no data available
Melting point/ freezing point:    5\u00b0C(lit.)
Boiling point or initial boiling point and boiling range: 277\u00b0C(lit.)
Flammability: Combustible.
Lower and upper explosion limit / flammability limit: no data available
Flash point: >93\u00b0C
Auto-ignition temperature: no data available
Decomposition temperature: no data available
pH: no data available
Kinematic viscosity: no data available
Solubility: less than 1 mg/mL at 20.5\u00b0C
Partition coefficient n-octanol/water (log value): -1.81 (calculated)
Vapour pressure: Pa at 25\u00b0C: 0.03 (negligible)
Density and/or relative density: 1.074g/mLat 25\u00b0C
Relative vapour density: no data available
Particle characteristics: no data available

Chemical Formula: C4H7NO2
Average Molecular Mass: 101.105 g/mol
Monoisotopic Mass: 101.048 g/mol
CAS Registry Number: 924-42-5
IUPAC Name: N-(hydroxymethyl)prop-2-enimidic acid
Traditional Name: N-(hydroxymethyl)prop-2-enimidic acid
InChI Identifier: InChI=1S/C4H7NO2/c1-2-4(7)5-3-6/h2,6H,1,3H2,(H,5,7)

Appearance: White crystal
Content: ≥98%
Melting point: 70-74°C
PH: 7-7.5
Moisture: ≤1.5%
Free formaldehyde: ≤0.3%

2-Propenamide, N- (hydroxymethyl)-
2-Propenamide, N-(hydroxymethyl)-
Acrylamide, N- (hydroxymethyl)-
Acrylamide, N-(hydroxymethyl)-
N-Hydroxymethyl acrylamide
Uramine T 80
Yuramin T 80

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