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Home > Encyclopedia > Poly(2-hydroxypropyl methacrylate)

Poly(2-hydroxypropyl methacrylate)

Poly(2-hydroxypropyl methacrylate) structure

Poly(2-hydroxypropyl methacrylate) 

structure
  • CAS No:

    25703-79-1

  • Formula:

    (C7H12O3)x

  • Chemical Name:

    Poly(2-hydroxypropyl methacrylate)

  • Synonyms:

    2-Propenoic acid,2-methyl-,2-hydroxypropyl ester,homopolymer;Methacrylic acid,2-hydroxypropyl ester,polymers;Methacrylic acid,2-hydroxypropyl ester,homopolymer;1,2-Propanediol,1-methacrylate,polymers;2-Hydroxypropyl methacrylate polymer;Poly(2-hydroxypropyl methacrylate);2-Hydroxypropyl methacrylate homopolymer;Light Ester HOP homopolymer;Light Ester HOP(N) homopolymer;2243291-48-5

  • Categories:

    Catalyst and Auxiliary  >  Polymer

Description

white to off-white crystals or granules


Crystals or white crystalline solid. (NTP, 1992)|Liquid


Crystals or white crystalline solid. (NTP, 1992)|2-hydroxypropyl methacrylate is an enoate ester that is the 1-methacryloyl derivative of propane-1,2-diol. It has a role as a polymerisation monomer. It derives from a propane-1,2-diol and a methacrylic acid.

Poly(2-hydroxypropyl methacrylate) Basic Attributes

144.17

144.07900

213-090-3

DTXSID1025934|DTXSID5027936|DTXSID1029629|DTXSID4093938

Clear liquid

39069090

Characteristics

46.5

0.48650

White to off-white crystalline

1.027g/cm3

430 to 433° F (NTP, 1992)

218.8ºC at 760mmHg

86.9ºC

1.444

less than 1 mg/mL at 73° F (NTP, 1992)

Temp during storage must be kept low to minimize formation of peroxides and other oxidation products. ... Storage temp below 30 °C are recommended for the polyfunctional methacrylates. ... The methacrylate monomers should not be stored for longer than one year. Shorter storage times are recommended for the aminomethacrylates, ie, three months, and the polyfunctional methacrylates, ie, six months. Many of these cmpd are sensitive to UV light and should, therefore, be stored in the dark. The methacrylic esters may be stored in mild steel, stainless steel, or aluminum. /Methacrylic acid & derivatives/

0.0262mmHg at 25°C

Slight acrylic odor

Mobile|Heat of polymerization: ~50 kJ/mole /2-Hydroxypropyl methacrylate/

Insoluble in water.

Alcohols and Polyols

Polymerizable

POLY(2-HYDROXYPROPYL METHACRYLATE) will react as an ester. The reactivity of the ester group depends a great deal on the degree of polymerization. More highly polymerized material is also more inert to reaction. Read about ester reactive group in program literature.

Safety Information

NONH for all modes of transport

3

S24/25

P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P333+P313, P337+P313, P363, P501

H317

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.

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

|Warning|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P333+P313, P337+P313, P363, and P501|Aggregated GHS information provided by 225 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. You should then dampen the solid spill material with 60-70% methanol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with methanol to pick up any remaining material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash contaminated surfaces with 60-70% methanol followed by washing 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 store this material under ambient temperatures. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)|SUITABLE PROTECTIVE CLOTHING & SELF-CONTAINED RESP PROTECTIVE APPARATUS SHOULD BE AVAILABLE FOR USE OF THOSE WHO MAY HAVE TO RESCUE OF PERSONS OVERCOME BY FUMES. /ACRYLIC ACID & DERIVATIVES/|Goggles or face shield; rubber gloves.

Combustible

Fire fighting agents: Foam, dry chemical, carbon dioxide. Water may be ineffective.

... Hazard is the generation of considerable exothermic heat in some of the reactions, so that high pressures & temp may develop. This danger ... should be borne in mind when designing plant. Awareness of the dangers and of good engineering design are essential to safety. Employees should be instructed about the necessity of cleansing the skin if it is contaminated by materials which are irritants or skin-absorbed. With careful design, however, and complete enclosure of those processes where toxic chemicals or intermediates occur, dangerous exposures can be avoided. /Acrylic acid & derivatives/|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Vapor: Irritating to eyes, nose and throat. Liquid: Irritating to eyes.

Toxicity

LD50 MOUSE ORAL 6.0 ML/KG

Drug Information

SMALL QUANTITIES OF METHACRYLATES MAY READILY BE METABOLIZED BY SAPONIFICATION INTO THE ALCOHOL AND METHACRYLIC ACID. THE LATTER MAY FORM AN ACETYL-COENZYME A DERIVATIVE, WHICH THEN ENTERS THE NORMAL LIPID METABOLISM. /METHACRYLATES/

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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. 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. INGESTION: DO NOT INDUCE VOMITING. 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. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Basic treatment: Establish a patent airway. Suction if necessary. Encourage patient to take deep breaths. Watch for signs of respiratory insufficiency and assist ventilations 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 ... . Anticipate seizures 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 ... . /Irritating materials/|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 if necessary ... . Start an IV with D5W TKO /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 ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Irritating materials/

2-hydroxypropyl methacrylate

Poly(2-hydroxypropyl methacrylate) Use and Manufacturing

Methods of Manufacturing

ADDITION OF PROPYLENE OXIDE TO METHACRYLIC ACID WITH A BASE AS CATALYST|Hydroxyalkyl methacrylates are prepared by the addition of methacrylic acid to the epoxide ring of alkylene oxides to form hydroxyalkyl methacrylates, ie, beta-hydroxyethyl and hydroxypropyl methacrylate. Oxides other than ethylene oxide give isomeric products; commercial hydroxypropyl methyacrylate has about a 2-to-1 ratio of 2-hydroxypropyl methacrylate to 1-methyl-2-hydroxyethyl methacrylate. Effective catalysts include tertiary amines, anion-exchange resins, ferric chloride, and lithium methacrylate.|The methacrylates can be synthesized by catalytic oxidation of isobutylene and subsequent esterification with the appropriate alcohol, or by reacting acetone with hydrocyanic acid and subsequent esterification in sulfuric acid with the appropriate alcohol. /Methacrylic esters/

Uses

Adhesives and sealant chemicals


Adhesives and sealants|Paints and coatings

Production

1,000,000 - 10,000,000 lb|500,000 - 1,000,000 lb

100% AS MONOMER

Inhibitior of polymerization: 200 ppm hydroquinone|Grades of purity: Commercial, 95+%|Typical inhibitor level: 1200 ppm monomethyl ether hydroquinone

(golf club)|2-Propenoic acid, 2-methyl-, monoester with 1,2-propanediol: ACTIVE|Paint and coating manufacturing|2-Propenoic acid, 2-methyl-, 2-hydroxypropyl ester: ACTIVE|2-Propenoic acid, 2-methyl-, 2-hydroxypropyl ester, homopolymer: INACTIVE|XU - indicates a substance exempt from reporting under the Chemical Data Reporting Rule, (40 CFR 711).|2-Propenoic acid, 2-methyl-, monoester with 1,2-propanediol, homopolymer: INACTIVE|METHYL METHACRYLATE, AND IN GENERAL THE METHACRYLIC ESTERS, POLYMERIZE MUCH LESS READILY THAN THE CORRESPONDING ORDINARY ACRYLATES. NONE THE LESS, THEY ARE STABILIZED BY ADDING HYDROQUINONE OR PYROGALLOL, PARTICULARLY IN THE PRESENCE OF METALLIC COPPER. /METHACRYLATES/

Thin-layer chromatography (TLC), polarography, and spectrometry are used for soln measurements. Methacrylates in air have been analyzed by TLC, polarography, and colorimetry. Polarography has been used for determination of any residual monomer in the polymer. A variety of spectroscopic techniques, eg, NMR, IR, and Raman spectroscopy also have been used, particularly for analysis of surgical cements and dental restorative resins. /Methacrylic acid & derivatives/

Computed Properties

Molecular Weight:144.17
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:144.078644241
Monoisotopic Mass:144.078644241
Topological Polar Surface Area:46.5
Heavy Atom Count:10
Complexity:140
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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