HPMA

N-(2-Hydroxypropyl)methacrylamide =  2-Hydroxypropyl Methacrylate = HPMA

CAS NO: 21442-01-3
EC NO:248-666-3
Chemical formula: C7H13NO2

N-(2-Hydroxypropyl)methacrylamide or HPMA is the monomer used to make the polymer poly(N-(2-hydroxypropyl)methacrylamide).

The polymer is water-soluble (highly hydrophilic), non-immunogenic and non-toxic, and resides in the blood circulation well. 
Thus, HPMA is frequently used as macromolecular carrier for low molecular weight drugs (especially anti-cancer chemotherapeutic agents) to enhance therapeutic efficacy and limit side effects.
Poly(HPMA)-drug conjugate preferably accumulates in tumor tissues via the passive-targeting process (or so-called EPR effect). 
Due to its favorable characteristics, HPMA polymers and copolymers are also commonly used to produce synthetic biocompatible medical materials such as hydrogels.

The development of pHPMA as anti-cancer drug delivery vehicles is initiated by Dr. Jindřich Kopeček and colleagues at the Czech (-oslovak) Academy of Sciences in Prague in the mid-1970s.
Prior to this, HPMA was used as a plasma expander. 
The Kopeček Laboratory designed and developed HPMA copolymer-drug conjugates as a lysosomal delivery vehicle to cancer cells. 
The concept of using pHPMA as polymeric drug carriers has opened a new perspective in modern pharmaceutical science, and developed into the first polymer-drug conjugate entering clinical trials (i.e. PK1; HPMA copolymer-doxorubicin conjugate).

The HPMA copolymers are also used as a scaffold for iBodies, polymer-based antibody mimetics.

Names
IUPAC name
N-(2-Hydroxypropyl)methacrylamide
Preferred IUPAC name
N-(2-Hydroxypropyl)-2-methylprop-2-enamide

2-Hydroxypropyl Methacrylate (HPMA) is an ester of Methacrylic acid and is used as a raw material component in the synthesis of polymers. 2-Hydroxypropyl Methacrylate (HPMA) is a functional hydrophobic hydroxy monomer consisting of a methacrylate group with a characteristic high reactivity and a cyclic hydrophobic group. 2-Hydroxypropyl Methacrylate (HPMA) forms a homopolymer and copolymers. Copolymers of 2-Hydroxypropyl Methacrylate (HPMA) can be prepared with (meth)acrylic acid and its salts, amides, and esters, as well as with (meth)acrylates, acrylonitrile, maleic acid esters, vinyl acetate, vinyl chloride, vinylidene chloride, styrene, butadiene, and other monomers.

HPMA easily entering into the reaction of accession with a wide range of organic and inorganic substances, is used for the synthesis of organic low molecular weight substances.

Product Type: Methacrylate Monomer

Features & Benefits:
Chemical resistance
Hydraulic stability
Hydrophobicity
Flexibility
Adhesion
Shock resistance
Weather resistance

Applications areas:
HPMA used in the preparation of solid and emulsion polymers, acrylic dispersions in combination with other (meth) acrylates, which are used in various industries, especially for textile coatings and dressings.
HPMA is widely used in the production of acrylic polyols for automotive components, refurbishment coatings, and industrial coatings. 
HPMA is also used as a comonomer in styrene-based unsaturated polyesters, PMMA-based acrylic resins, and vinyl ester formulations in anchor bolts and chemical anchors. 
HPMA is particularly useful as a hydrophobic hydroxy monomer in the manufacture of sealants for vacuum impregnation of cast aluminum components. 
HPMA is also widely used in the production of flexible UV-curable photopolymer printing plates.

HPMA is applied in the production of:
Automotive coatings
Architectural coatings
Industrial coatings
Plastics
Hygiene products
Adhesives & Sealants
Textile finishes
Modifications
Photosensitive materials
Additives for oil production and transportation

Safety
HPMA is a combustible substance. With intense healing, it forms explosive vapors with air. Vapors are heavier than air and may spread along with floors. In case of fire formation of harmful gaseous products is possible. Contact with skin may cause an allergic reaction. Flash-point is 101 °C. The ignition temperature is 355 °C. 
When working with HPMA, sanitary rules for organizing technological processes and hygienic requirements for production equipment must be strictly observed. All types of work with GPMA should be carried out in rooms equipped with general supply and exhaust ventilation. 
HPMA is not allowed to carry out work in these rooms using an open fire. 
Those working with HPMA should be provided with special clothing and personal protective equipment. In case of fire, it is necessary to use fire extinguishers OP-5, OVP-100 koshma, sand, asbestos cloth.
HPMA spilled on solid soil should be covered with sand.

Uses:
Chemical Manufacturing and Industrial
Paints, Inks and Coatings

Benefits:
Hydrophilicity
Improved adhesion to substrates
Crosslinking sites, free hydroxy group reacts readily with isocyanate, anhydrides and 
epoxy resins
Corrosion, fogging, and abrasion resistance, as well as contribute to low odor, color, and 
volatility

Hydroxypropyl methacrylate (HPMA). 
HPMA is a clear, colourless liquid with a characteristic odour. 
HPMA is an ester of methacrylic acid. 
HPMA is relatively non-volatile, non-toxic and non-yellowing. 
HPMA copolymerizes readily with a wide variety of monomers, and the added hydroxyl groups improve adhesion to surfaces, incorporate cross-linking sites, and impart corrosion, fogging, and abrasion resistance, as well as contribute to low odour, colour, and volatility. 
HPMA is used in the manufacture of acrylic polymers for adhesives, printing inks, coatings and metal applications. 
HPMA is also used as reactive diluent and alternative to styrene in unsatured polyester (UPR).
HPMA compared to HEMA is more suitable when a better water resistance is required, together with a better shrinkage resistance.

HPMA is a functional monomer that can copolymerize with other monomers to produce copolymers with a hydroxy group in the side chain. Hydroxyesters are recommended for heat or room temperature cured coatings with permanent marring and solvent resistance, high gloss retention and weatherability.
HPMA is a difunctional, hydrolytically stable, hydrophilic monomer, a building blocks of modified and new biomaterials.

MELTING POINT: 67°
MOLECULAR WEIGHT:143.2

HPMA is the monomer used to make the polymer poly(N-(2-hydroxypropyl)methacrylamide). 
HPMA is water-soluble (highly hydrophilic), non-immunogenic and non-toxic, and resides in the blood circulation well. 
Thus,HPMA is frequently used as macromolecular carrier for low molecular weight drugs (especially anti-cancer chemotherapeutic agents) to enhance therapeutic efficacy and limit side effects. 
HPMA conjugate preferably accumulates in tumor tissues via the passive-targeting process (or so-called EPR effect). Due to its favorable characteristics, HPMA polymers and copolymers are also commonly used to produce synthetic biocompatible medical materials such as hydrogels.

HPMA is an enoate ester that is the 1-methacryloyl derivative of propane-1,2-diol. 
HPMA has a role as a polymerisation monomer.
HPMA derives from a propane-1,2-diol and a methacrylic acid.

Industry Uses        
Adhesives and sealant chemicals
Intermediates
Paint additives and coating additives not described by other categories
Processing aids, not otherwise listed
Adhesives and sealant chemicals
Paint additives and coating additives not described by other categories
Producing resin for paint coating and adhesive

Consumer Uses        
Adhesives and sealants
Electrical and electronic products
Paints and coatings
Plastic and rubber products not covered elsewhere
Resin Products.
Toys, playground, and sporting equipment

Industry Processing Sectors
(golf club)
Adhesive manufacturing
All other basic organic chemical manufacturing
Electrical equipment, appliance, and component manufacturing
Miscellaneous manufacturing
Paint and coating manufacturing
Plastic material and resin manufacturing
Wood product manufacturing

Chemical Properties
Clear colorless liquid
Uses
Monomer for acrylic resins, nonwoven fabric binders, detergent lubricating-oil additives.
General Description
White liquid with a light unpleasant odor. May float or sink in water.
Reactivity Profile
HPMA  polymerization: May polymerize when hot or when exposed to ultraviolet light and free-radical catalysts [USCG, 1999].

HPMA is a phosphorus-free water treatment chemical. 
HPMA forms a chelate with calcium and magnesium ions in water. And HPMA can cause lattice distortion. After the anion is adsorbed by the calcium carbonate nucleus, the nucleus can be charged.

Due to the homophobic electrical repelling, tiny grains are dispersed in the aqueous solution. HPMA is converted into a loose slag with good fluidity. 
HPMA has a good effect on peeling off the old scale.

HPMA is compatible with other low-phosphorus corrosion and scale inhibitors such as ATMP and PBTCA. 
The formed composite corrosion and scale inhibitor can be widely used in the treatment of circulating cooling water, boiler water, oil field water injection, industrial water.

HPMA Structural Analysis
HPMA is the product of partial hydrolysis of polymaleic anhydride.
HPMA has been determined that about 60% to 70% of the HPMA is hydrolyzed to a carboxylic acid. That is not completely hydrolyzed.

HPMA is shown by the study of the structure-effect relationship of molecular microstructure. 
The increase in the degree of hydrolysis is advantageous for HPMA chemical improvement in scale inhibition performance. Therefore, a large degree of hydrolysis is ensured as much as possible during synthesis of HPMA.

From HPMA structural analysis, its carboxyl group in the molecule can form compounds with calcium and magnesium ions in water. 
And HPMA can promote lattice distortion and turn the precipitation into a loose slag with good fluidity.

HPMA is the same as a polymer having a hydroxyl group or a sulfonic acid group.
HPMA can be dissociated into hydrogen ions and acid anions after being dissolved in water. The chain molecules are then negatively charged.

This long-chain negatively charged anion is adsorbed by calcium carbonate nucleus and fine crystal grains. 
Then bring HPMA with a more negative charge.

The crystallites are dispersed into the aqueous solution due to the homophobic electrical repelling. 
This prevents the fine grains from coagulating to form larger crystals. 
Thus, HPMA has a dissolution limiting effect. 
HPMA has high scale inhibition performance when used at low doses.

In addition, the carbonyl group of HPMA has a strong complexation as an electron donor. 
This changes the normal morphology of calcium carbonate and calcium phosphate crystals. And can prevent HPMA from growing into a larger crystal. 
Thereby HPMA has the effect of inhibiting scale formation and peeling off the old scale.

HPMA Characteristics
HPMA chemical is a class of polycarboxylic acid scale inhibitors.
HPMA can be matched with other corrosion inhibitors and scale inhibitors. 
The molecular weight of HPMA is about 600~1200. The aqueous solution is brownish yellow or brownish red, viscous, acidic liquid. 
HPMA is chemically stable. 
HPMA can be used at temperatures below 350 °C.

HPMA has excellent scale inhibition performance for carbonate and phosphate. 
HPMA has significant solubility effects and significant dispersion effects. 
HPMA can be adapted to water quality at different pH values. 
HPMA chemical is phosphorus-free, non-toxic and environmentally friendly. 
HPMA can be degraded by microorganisms in the natural environment. The degradation products have no effect on the ecological environment.

HPMA Scale Inhibition Performance
The HPMA has the following scale inhibition characteristics.

(1)HPMA is quite effective for calcium carbonate scale. At the same time, it has both lattice distortion and threshold effect (ie, unidirectional conductivity). Even if it is scaled, it is relatively loose.
HPMA is easily washed away by water and not formed into a hard scale.

(2) HPMA has high-temperature resistance. Decomposition usually occurs above 350 °C. Can be used at high temperatures.

(3) HPMA has a certain ability to disperse calcium carbonate, calcium phosphate, calcium sulfate and the like.

(4)HPMA can be compounded with a zinc salt. There is a synergistic effect on corrosion inhibition of carbon steel.

(5) HPMA is non-toxic. No significant impact on the environment.

The HPMA chemical corrosion inhibition mechanism is as follows.

The oxygen atom in the polar group (—COOH) and (—OH) in the HPMA molecule can become the adsorption center.
HPMA can form a chelate with metal ions in water. Adsorbed on the metal surface. A protective film is formed along the metal surface. Thereby playing a role in corrosion inhibition.

A single polymaleic anhydride is an excellent scale inhibitor. The corrosion inhibition performance is poor. Compared with polyacrylic acid and polymethacrylic acid, HPMA  corrosion inhibition performance is slightly stronger. C-P bonds and phosphinic acid groups (-PO2H2) are usually introduced to enhance corrosion inhibition performance.

Compound Scale Inhibitor
1.HPMA-ATMP Compound
ATMP plays a major role as a water quality stabilizer. One is the cooperation of ATMP. It can both soften water and descale. Second, ATMP interferes with the growth of the CaCO3 scale layer. ATMP causes a large distortion of the CaCO3 crystal structure.

2.HPMA-PESA Compound
PESA has a phosphorus-free, non-nitrogen structure. It can be biodegraded in the natural environment. PESA has the dual functions of scale inhibition and corrosion inhibition.

The complex paired calcium carbonate scale of HPMA-PESA has good scale inhibition performance. The concentration, temperature and concentration time of the scale inhibitor have a great influence on the scale inhibition effect.

Increasing the amount of HPMA-PESA compounding agent can also increase the scale inhibition performance of calcium carbonate. When HPMA-PESA is added to a certain amount, it will tend to be saturated and gentle. This composite formulation was the largest at a concentration time of 10 hours. As the concentration-time is further extended, the scale inhibition rate begins to decrease slowly.

3.HPMA-EDTMPS Compound
EDTMPS water miscible energy is chelated with multiple metal ions. A plurality of monomeric structure macromolecular network complexes is formed. EDTMPS destroys the normal crystallization of calcium scale. HPMA-EDTMPS compound scaling rate is greatly improved.

4.HPMA-PAA Compound
PAA is an excellent scale inhibitor and dispersant. It has a good effect of inhibiting the formation of scale and peeling off the old scale. The reaction can be carried out under alkaline and medium concentration multiple conditions without fouling.

As a new type of composite scale inhibitor, HPMA-PAA has the advantages of good scale inhibition effect and good thermal stability.

5.HPMA and HEDP, AMPS Ternary Compounding
The polymer corrosion and scale inhibitor molecules contain two important groups of “stabilizing groups” and “docking groups”. The docking group is adsorbed on the crystallites. Poor water solubility and strong adsorption. The stabilizing group has a good affinity with the solvent.

A large number of carboxyl groups on HPMA are negatively charged after ionization. 
HPMA is an excellent stable group. The amide group on 2-acryloyl-methylpropane sulfonic acid (AMPS) has strong adsorption to the scale-forming crystallites. 
It is an excellent docking group. HEDP easily forms a six-membered ring chelate with metal ions and has a synergistic effect.

HPMA is compounded with APMS and HEDP. Excellent docking groups are introduced in the polymaleic anhydride molecule. The adsorption of the polymer is improved. Thereby increasing the “lattice distortion” and “adsorption dispersion” of the polymer. And temperature resistance and timeliness. Very few scale inhibitors can achieve higher scale inhibition rate

SYNONYMS:
21442-01-3 [RN]
2-hydroxypropyl methacrylamide
2-Propenamide, N-(2-hydroxypropyl)-2-methyl- [ACD/Index Name]
HPMA
methacryloylamino-2-hydroxypropane
MFCD00080531
N-(2-Hydroxypropyl) methacrylamide [Wiki]
N-(2-Hydroxypropyl)-2-methylacrylamid [German] [ACD/IUPAC Name]
N-(2-Hydroxypropyl)-2-methylacrylamide [ACD/IUPAC Name]
N-(2-Hydroxypropyl)-2-méthylacrylamide [French] [ACD/IUPAC Name]
N-(2-hydroxypropyl)-2-methyl-prop-2-enamide
N-(2-HYDROXYPROPYL)METHACRYLAMIDE
N-(2-hydroxypropyl)methacrylamide)
R3F262Z4E0
UNII:R3F262Z4E0
[21442-01-3]
1-(4-Fluorophenyl)-4-[(6bR,10aS)-2,3,6b,9,10,10a-hexahydro-3-methyl-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl]-1-butanone 4-methylbenzenesulfonate;1-(4-fluorophenyl)-4-[(6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl]butan-1-one toluenesulfonic acid