1,6-ビス(アクリロイルオキシ)ヘキサン

log Kow = 3.08 /Estimated/

3.08

greater than 200 °F (NTP, 1992)

>200 °F

0.01 [mmHg]

0.017 mm Hg @ 25 °C /Estimated/

0.017 [mm Hg] @25 °C

1,6-hexanediol diacrylate is a clear yellow liquid. (NTP, 1992)

CBI; Liquid

Clear yellow liquid; [CAMEO]

Clear yellow liquid with a mild ester-like odor.

Warning

H315: Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (2 of 3404) of reports.

Warning

H315 (> 99.9%): Causes skin irritation [Warning Skin corrosion/irritation]

Chemical: 2-Propenoic acid, 1,6-hexanediyl ester

2-Propenoic acid, 1,1'-(1,6-hexanediyl) ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 1,1'-(1,6-hexanediyl) ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 08-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14690

1,6-Hexanediol diacrylate: Does not have an individual approval but may be used under an appropriate group standard

Allergic contact dermatitis reported in a laboratory worker in a paint manufacturing factory; [Kanerva, p. 1742] Can undergo exothermic polymerization reactions; Temperature sensitive; May auto-oxidize on exposure to air forming explosive peroxides; [CAMEO] Classified in the EU as a skin and eye irritant with the possibility of causing skin sensitization; [IUCLID] May spontaneously polymerize; A skin and strong eye irritant; May cause skin sensitization; [Alfa Aesar MSDS]

1,6-HEXANEDIOL DIACRYLATE is temperature sensitive (NTP, 1992). May react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release gaseous hydrogen. Can undergo very exothermic addition polymerization reactions. May undergo autoxidation upon exposure to the air to form explosive peroxides.

Skin Irrit. 2 (> 99.9%)

Eye irritation - category 2

Skin sensitization - Category 1

Skin corrosion/irritation - Category 2

Skin Irrit. 2

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.

The effectiveness of phenolic inhibitors is dependent on the presence of oxygen and the monomers must be stored under air rather than an inert atmosphere. Temp must be kept low to minimize formation of peroxides and other products. Moisture may cause rust-initiated polymerization. /Acrylic acid & derivatives/

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong 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.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

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: 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.

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.

3.0 [mg/m3]

170 [mg/m3]

990 [mg/m3]

RECOMMENDED RESPIRATOR: When working with this chemical, wear a NIOSH-approved full face chemical cartridge respirator equipped with the appropriate organic vapor cartridges. If that is not available, a half face respirator similarly equipped plus airtight goggles can be substituted. However, please note that half face respirators provide a substantially lower level of protection than do full face respirators. (NTP, 1992)

Suitable protective clothing and self-contained respiratory protective apparatus should be available for use of those who may have to rescue persons overcome by fumes. /Acrylic acid and derivatives/

... Gloves and protective clothing and shoes or boots should be used in addition to eye (or full face) protective equipment. /Acrylic acid & derivatives/

1,6-Hexanediol diacrylate (HDODA; CASRN 13048-33-4) was applied at a rate of 0 or 300 mg/kg once daily to the clipped backs of New Zealand White rabbits (5/sex/group) for 5 days/week for 2 weeks (10 treatments). The skin of 3 animals/sex/group was abraded. The treatment sites were left uncovered. Fifteen days after the initial treatment, 3 abraded-skin rabbits and 3 non-abraded rabbits (regardless of sex) were sacrificed. Two weeks following the last treatment, the remaining animals were sacrificed. One mortality in the treated group occurred on day 21; the cause was not determined. Treated animals exhibited erythema and edema at the application site after one dose. By the end of the second week, all treated animals showed severe erythema, slight to moderate edema, fissuring of the skin, desquamation, and eschar formation. Of the treated animals, 3 experienced slight weight loss, and several exhibited nasal discharge and loss of motor activity; these symptoms were attributed to causes other than treatment. At the interim sacrifice, microscopic examination of the skin revealed moderate irritation. At terminal sacrifice, skin sections showed intact epithelium but moderate to severe irritation. Microscopic examination of selected tissues revealed no evidence of systemic toxicity resulting from treatment with 300 mg/kg HDODA.

1,6-Hexanediol diacrylate (HDODA; CASRN 13048-33-4) was evaluated for carcinogenic potential. The backs of male C3H/HeJ mice (50/group) were clipped and 50 mg HDODA in a 5% solution of mineral oil was applied to the interscapular region and left uncovered ; exposures occurred twice weekly for 80 weeks. Three control groups were included: a no-treatment group; a solvent control group; and a positive control group in which a solution of 0.05% benzo(a)pyrene in mineral oil was used. One HDODA animal developed fibrosarcoma at the application site. It was noted as being a very low rate of incidence compared with the positive controls. Non-neoplastic lesions such as ulcer (1), acanthosis (34), fibrosis (35), excess pigment (4), and hyperkeratosis (5) were also noted.

1,6-Hexanediol diacrylate (C-255; CAS# 13048-33-4) was evaluated for tolerance in pregnant Sprague-Dawley CD rats. Inseminated female rats (6/group) were given 100, 500, or 1000 mg/kg C-255 in corn oil/day by oral gavage on days 6-15 of gestation. A control group received corn oil only. There were no mortalities reported. Urine stains, bloody crust, rough haircoat, and salivation were noted in some rats receiving 1000 mg/kg. The mean body weight change from days 6-15 in the 1000 mg/kg group was lower than controls. Gross examination at terminal sacrifice (day 16 of gestation) revealed rough or white areas in the stomach in 2 rats receiving 500 mg/kg C-255. Mean ovarian and uterine data were comparable to controls. No other observations were reported.

/HUMAN EXPOSURE STUDIES/ /Brief/ topical contact with 1,6-hexanediol diacrylate may cause delayed irritant dermatitis. During a 4 yr observation of 20 workers, contact sensitization did not occur.

/SIGNS AND SYMPTOMS/ Human signs and symptoms following ingestion of acrylic monomers include collapse, severe respiratory difficulties, and CNS stimulation. /Acrylates/

/SIGNS AND SYMPTOMS/ Allergic reactions have been reported for some acrylates. /Acrylates/

/CASE REPORTS/ ... We report two cases of workers in the printing industry who developed allergic contact dermatitis to 1,6-hexanediol diacrylate (HDDA) within a short period of exposure. The first developed within weeks of exposure to a plastic sheet primed with HDDA. The second developed after a single accidental exposure.

/CASE REPORTS/ A case of sensitization after a single occupational exposure to 1,6-hexanediol-diacrylate (HDDA) was reported in an employee in a plastic paint factory.

/LABORATORY ANIMALS: Acute Exposure/ The acute toxicity of the acrylates decreases with increasing molecular weight. ...Acute inhalation of higher concentrations may cause narcosis, salivation, and pronounced nasal, ocular, and pulmonary irritation or edema. Prolonged skin or eye contact may result in severe tissue damage. /Acrylates/

/LABORATORY ANIMALS: Acute Exposure/ Studies with animals confirm that diacrylates, including 1,6-hexanediol diacrylate, are more irritating than dimethacrylates and the magnusson & kligman method shows that the substances induce delayed hypersensitivity.

/LABORATORY ANIMALS: Acute Exposure/ Contact sensitivity was produced in guinea pigs with mono-, di-, and tri- acrylate compounds. /Mono-, di-, and tri- acrylate compounds/

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ The pathology from single exposure is not particularly characteristic, contrary to repeated exposure effects, which include pulmonary congestion or hemorrhage and cloudy swelling and organ weight changes of the liver and kidney, reported following subchronic exposures to excessive concentrations. /Acrylates/

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Animal studies using rats revealed that some acrylates and methacrylates are embryotoxic. The doses of monomers used in the animal studies, however, were much higher than concentrations likely encountered by workers. /Acrylates and Methacrylates/

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/

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. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /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 ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

LD50 Rabbit dermal 3600 mg/kg

LD50 Rat oral 5 g/kg

Acrylates and methacrylates are detoxified predominantly via conjugation with glutathione via the Michael addition reaction or glutathione-S-transferase. They are also likely to be hydrolyzed via carboxylesterases. The lower molecular weight esters are rapidly metabolized and eliminated, therefore, will not likely cause cumulative toxicity. /Acrylates/

Chemical intermediate and curing agent for polymers; [HSDB] Used as a cross-linking agent in UV-cured inks, coatings, adhesives, and dental sealants; [AIHA] Used for synthesis in the chemical industry, in paints, lacquers, and varnishes, in photochemicals and the photographic industry, and as intermediate; [IUCLID]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

CROSSLINKING AGENT FOR UV-CURABLE POLYMERS, EG, COATINGS

CHEM INT FOR POLYMER WITH ETHANOLAMINE

CHEM INT FOR POLYMER WITH SUCCINIC ANHYDRIDE

CHEM INT FOR POLYMER WITH 4-METHOXYPHENOL

2023: 10,000,000 - <25,000,000 lb

(1979) PROBABLY GREATER THAN 4.54X10+6 G

(1981) PROBABLY GREATER THAN 4.54X10+6 G

ESTERIFICATION OF 1,6-HEXANEDIOL WITH ACRYLIC ACID

In ... propylene oxidation process acrolein is first formed by the catalytic oxidation of propylene vapor at high temp in the presence of steam. The acrolein is then oxidized to acrylic acid. ... The acrylic acid is esterified with alcohol to the ... acrylic ester in a separate process. /Acrylic ester monomers/

The acrylates can be manufactured by a number of procedures. These include dehydration of the corresponding hydroxyalkanoic acid, saponification of the alkaline nitrile, catalytic hydration of acetylene and carbon monoxide, or the reaction of acetone with hydrocyanic acid. /Acrylates/

Printing Ink Manufacturing

2-Propenoic acid, 1,1'-(1,6-hexanediyl) ester: ACTIVE