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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].
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
