N-METHYLOLACRYLAMIDE 48%

N-Methylolacrylamide %48 solution = n-(hydroxymethyl)acrylamide = NMA

CAS-number: 924-42-5
EC / List no.: 213-103-2
Molecular Formula: C4H7NO2
Molecular Weight: 101.1


N-Methylolacrylamide %48 solution is a colorless liquid. 
N-Methylolacrylamide %48 solution produces post-crosslinking site in polymers. 
N-Methylolacrylamide %48 solution complies with TSCA regulation, Blend of N-Methylolacrylamide, water, acrylamide and formaldehyde.
N-Methylolacrylamide %48 solution has excellent co-solubility with divalent and trivalent cations and quaternary ammonium surfactants, so that N-Methylolacrylamide %48 solutions dissolution, compatibilization, lime soap dispersibility and other properties have improved greatly.
N-Methylolacrylamide %48 solution can not only be used alone, but also As the main Emulsifier with other anionic, non-ion or even multi-valent cationic surfactants used. 
N-Methylolacrylamide %48 solution Widely used in foam cement, leather, dyes, coatings, adhesives, especially the emulsion synthesis industry.
N-Methylolacrylamide %48 solution is worth mentioning that when the emulsion is polymerized, N-Methylolacrylamide %48 solution is particularly suitable for the synthesis of vinyl acetate emulsion, vinegar emulsion, vinegar and acrylic emulsion and pure acrylic emulsion.
N-Methylolacrylamide %48 solution can give the emulsion smaller particles, produce high solid low viscosity emulsion.
N-Methylolacrylamide %48 solution is a very important and effective latex particle size improver; and can be used as a post-addition stabilizer for the production of latex, and it is also a very important and effective latex particle size improver; . 
For self-crosslinking emulsions, HT A-103 does not affect cross-linking of cross-linked monomers such as N-methylol acrylamide, as with some Emulsifier, which does not contain any organic volatile components.

N-Methylolacrylamide is a bifunctional monomer with reactive vinyl and hydroxymethyl 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 hydroxymethyl 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 hydroxymethyl 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 %48 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.

N-Methylolacrylamide %48 is rapidly absorbed and slowly metabolised. 
NMA administered to rats intraveinously was distributed rapidly in body; its distribution in tissues and subcellularly is similar to that of acrylamide. 
N-Methylolacrylamide %48 is eliminated via glutathione conjugation and subsequent renal excretion which excludes bioaccumulation.
The mercapturate N-acetyl-S-(3-hydroxymethylamino-3-oxopropyl) cysteine, arising from direct conjugation of NMA with glutathione and subsequent metabolism, is the major urinary metabolite.
In addition to conjugation with GSH, other potential metabolic pathways, e.g by the P450 system, are unknown.
QSAR analysis by OECD toolbox supports the hypothesis of the conversion of NMA to AA.
However, there is no direct evidence if N-Methylolacrylamide %48 can be converted to acrylamide or an epoxide from in vivo studies in rodents.
DEREK modelisation shows consistent predictions regarding carcinogenicity and neurotoxicity between NMA and AA confirming their structural similarities. 
For genotoxicity, an additional alert was identified for NMA regarding mutagenicity in vitro. 


N-Methylolacrylamide is available commercially as a 48% aqueous solution with the following specifications: 
-assay, 48%
-water, 51-54% (tyically, 52%)
-pH, 5.5-6.5
-free formaldehyde, 1.5- 0: 3 wt%
-acrylamide, 0: 5.0 wt%
-copper, 2 ppm max.
-methylether of hydroquinone (inhibitor), 30 ppm
-specific gravity at 25 °C, 1.10 

Other physicochemical properties :
N-Methylolacrylamide is also available as a powder and an aqueous solution (48 %). 
The aqueous solution contains also acrylamide (< 5 %) and formaldehyde (< 2 % or < 0.5 %).

The physico - chemical properties are reported for a 48% aqueous solution of NMA containing formaldehyde and acrylamide as impurities. 

EVALUATION OF PHYSICAL HAZARDS
The substance is not classified for the physico-chemical aspect. 
See table of summary of physicochemical properties above. 
Physical hazards are not further assessed in this dossier.

Product Name: 
N-Methylolacrylamide

Freezing point (°C): -18 °C
Refractive index (25°C): approx. 1.4135

N-methylol acrylamide  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.

Therefore, N-Methylolacrylamide %48 can be questioned if proposing a classification entry for NMA is really justified in particular taking into account the classification of AA. 
However, N-Methylolacrylamide %48 remains that some registered compositions do not contain sufficient impurities to impact the classification of NMA (see confidential annex). 
In addition, N-Methylolacrylamide %48 is considered that NMA has intrinsic properties for carcinogenicity, genotoxicity and neurotoxicity to justify its own classification and Annex VI entry.


Treatment usefulness
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 %48-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.

Synonyms: 
2-Propenamide,N-(hydroxymethyl)-
Acrylamide, N-(hydroxymethyl)-
Monomethylolacrylamide
n-(hydroxymethyl)-2-propenamid
n-(hydroxymethyl)-acrylamid
NCI-C60333
NM-AMD
N-Methanolacrylamide

CAS: 924-42-5
MF: C4H7NO2
MW: 101.1
EINECS: 213-103-2


N-Methylolacrylamide %48 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 N-Methylolacrylamide %48 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 %48:
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 %48 (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, N-Methylolacrylamide %48 aqueous solution approximately, may be directly applied in the preparation of crosslinking polymers as a crosslinking agent.

Physical Description
N-Methylolacrylamide %48 appears as a colorless or yellow aqueous solution.

USAGE: N-Methylolacrylamide %48 is a kind of well chemical cross-linking agent. 
N-Methylolacrylamide %48 is mainly used for modification of fiber, resin manufacture, synthesis of adhesive, leather, paper-making, textile sizing agent, dope, cohesion of wood, petroleum exploitation, etc.

Total degradation in water :
Biodegradation:
type: aerobic
inoculum: activated sludge, domestic, non-adapted
concentration: 2 mg/l related to test substance
degradation: ca. 51.9 % after 28 day
result: not readily bidegradable
method: OECD Guide-line 301 D
test substance: The test article is containing 40-44 % N-methylolacrylamide in water (with < 5 % acrylamide and < 3 % formaldehyde)

NMA was synthesized via a random redox copolymerization, and the poly(NIPAAm-co-NMA) copolymer showed thermo-responsive properties. 
Here, NMA performed a thermal crosslinking function in the copolymer. Carbon black was acid-treated for good dispersion in an aqueous solution. 
Poly(NIPAAm-co-NMA)/CB composites were obtained by blending various amounts of acid-treated CB into the poly(NIPAAm-co-NMA) aqueous solution, and the films were then post-cured for thermal crosslinking. 
The properties of the conductive poly(NIPAAm-co-NMA)/CB films such as thermal crosslinking performance, surface resistance, and morphology of the crosslinked composites were investigated. 
This study demonstrated that the poly(NIPAAm-co-NMA)/CB composites exhibited both temperature-dependent electric resistance and reproducible thermally responsive characteristics. 
The composites can potentially be applied as new electrical temperature sensor materials.

Synonyms:    
n-methyloacrylamide
yuramin t 80
uraminet80 
rocagil bt 
nci-c60333 
uramine t 80 
n-man 
nm-amd 
methylolacrylamide
n-man pc
Formula: C4H7NO2

N-Methylolacrylamide %48 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.

There are different compositions of N-Methylolacrylamide %48 (NMA) claimed by the notifier.
There are some uncertainties regarding the impact of impurities on the classification of the substance NMA. 
An impact of both relevant impurities, acrylamide and formaldehyde, present in the different batches used in toxicological studies on the classification of the substance cannot be excluded. 
So N-Methylolacrylamide %48 is important to consider the different batches used in the different toxicological studies to conclude if the effects observed are related to NMA or to the impurities. 
NMA was tested using different batches with different purities. 

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)
InChI key: CNCOEDDPFOAUMB-UHFFFAOYSA-N


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 %48 an added stabilizer or inhibitor can influence the toxicological properties of this substance, consult an expert. 
N-Methylolacrylamide %48 is toxic to aquatic organisms. 
N-Methylolacrylamide %48 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. 


The composition of the substance tested in the toxicological studies was not fully clarified.
Furthermore, with a N-Methylolacrylamide %48 content above 97%, the toxicological batches are not the most appropriate to cover the substance as placed on the market (40 to 85% as aqueous solution). 
A carcinogenicity NTP assay (1989)1 reported that in the batch number 1-45-000 (batch used in most studies) NMA is present at a purity up to 98%, the impurities are unknown but evidence indicates that 1% may have been a polymer of NMA, which would not have been detected by the analytical methods used. 
Toxicity appears largely restricted to the monomer and acrylamide polymers are thought to pose little hazard to public health or the environment. 
So the polymers of N-Methylolacrylamide %48 can be considered of not toxicologically concern

There are some persistent doubts on the fact that the effects (mutagenicity, carcinogenicity and neurotoxicity) observed with NMA could be due to the presence of classified impurities content.
Indeed, for most of the compositions of N-Methylolacrylamide %48 registered under REACH regulation, the levels of formaldehyde and/or acrylamide should lead to a classification of the substance by calculation.

Some data on acrylamide (AA) have been reported here in order to assess the potential influence of AA on the toxicity of NMA. 
Indeed, in addition to be a potential impurity of N-Methylolacrylamide %48, it has been checked if AA could be a metabolite of NMA. 
This is of particular importance to conclude if the mutagenic, carcinogenic and neurotoxic effects reported in studies performed with NMA are related to the substance itself or to the presence of AA as an impurity or as a metabolite

Applications
NMA is an important chemical raw material, which is used to various high polymers widely, such as coating, adhesive, papermaking aid, etc.; it has huge applicability potential in chemical industry and science study.
 
In textile industry, the binders used are mostly water based acrylic dispersions. 
These binders provide strength, elastic recovery, soft hand, flexibility, color retention and also resistance to washing and aging to the textile and nonwoven. 
Nevertheless, binders having no reactive functional monomers are not very successful in imparting these properties.
Self crosslinking monomers are used to improve the properties of textile and non woven end products. 
N-Methylolacrylamide %48 (NMA) is one of these monomers having functional groups for self-crosslinking. 
However, N-Methylolacrylamide %48 used in textile binders emit formaldehyde during crosslinking at high temperatures. 
This formaldehyde either remains in the end product or is liberated into the air. 
The U.S. Department of Health and Human Services published the 12th Report on Carcinogens and formaldehyde is listed in the category of known to be a human carcinogen. 
Researchers on textile sector are focud on the subject of formaldehyde emission due to the harmfull effects on both people and environment. 
In this study, a novel monomer that emmits no formaldehyde and have ability to self-crosslink was investigated for replacement of NMA and the performance results are compared with that of NMA.

Rocagil BT
NCI-C60333
Yuramin T 80
Uramine T 80
METHYLOLACRYLAMIDE
N-Methyloacrylamide
n-(hydroxymethyl)-2-propenamide
N-methanolacrylamide
Monomethylolacrylamide
NCI-C60333
Uramine T 80
ACRYLAMIDE, N-(HYDROXYMETHYL)-
MH 100
MH 100 (AMIDE)
MONOMETHYLOLACRYLAMIDE
N-(HYDROXYMETHYL)-2-PROPENAMIDE
N-(HYDROXYMETHYL)ACRYLAMIDE
N-MAM P
N-METHANOLACRYLAMIDE
N-METHYLOLACRYLAMIDE
NCI-C60333
NMA 60
ROCAGIL BT
U-RAMIN T 80
URAMINE T 80

package
The solution is packed in 200kg plastic barrel and the crystal is in 10kg carton.

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

Storage and usage
N-Methylolacrylamide %48 must be kept in cool place, far away heat source and avoid exposure to forceful rays, because heat and rays can lead to polymerize NMA, in the presence of acid or foreign metals especially.Avoid the temperature exceed 28℃.  
Even N-Methylolacrylamide %48 is kept in good condition, the storage would be best less than 3 months.
The solution will be made crystal under -10℃, you can dissolve it by heating slowly with warm water bathe, the quality and capacity won’t be affected, N-Methylolacrylamide %48 is forbidden to open lid if the products in the barrel may be polluted. 
The utensil which is used to get it out and the container must be clean, tweak the lid quickly after get it out every time.
 
Safety and healthy  
Non-burning and non-burst, toxicity, forbidden to swallow and inhale, wash skin with run water if contact it.

Solubility:1880 g/l (20 °C)
Melting Point:-10 °C
Boiling Point:100 °C (1013 hPa)
Vapor Pressure:31 hPa (25 °C)
Flash Point:93 °C
Density:1.08 g/cm3 (20 °C)
pH:6.0 - 7.0 (H2O, 20 °C)

N-(Hydroxymethyl)acrylamide (48% aqueous solution) 
n-(hydroxymethyl)-2-propenamide
N-(HYDROXYMETHYL)ACRYLAMIDE
N-METHYLOLACRYLAMIDE
2-Propenamide,N-(hydroxymethyl)-
Acrylamide, N-(hydroxymethyl)-
Monomethylolacrylamide
n-(hydroxymethyl)-2-propenamid
n-(hydroxymethyl)-acrylamid
NCI-C60333; NM-AMD
N-Methanolacrylamide
N-Methyloacrylamide
n-methylolacrylamide(48%inwater)
Uramine T 80
uraminet80
Yuramin T 80
Methylolacrylamidesolution
N-MAN
N-(HYDROXYMETHYL)ACRYLAMIDE SOLUTION, ST AB., ~48% IN H2O
acrylamide, N-(hydroxymethyl)-
N-(hydroxymethyl)acrylamide
N-(hydroxymethyl)prop-2-enamide
N-methylol acryl amide
N-methylolacrylamide
2-propenamide, N-(hydroxymethyl)-
uramine T 80

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