1,6-Hexanediol diacrylate

Last updated
1,6-Hexanediol diacrylate
Hexandioldiacrylat.svg
Names
Preferred IUPAC name
Hexane-1,6-diyl di(prop-2-enoate)
Other names
HDDA, HDODA
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.032.641 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 235-921-9
PubChem CID
UNII
UN number 3082
  • InChI=1S/C12H18O4/c1-3-11(13)15-9-7-5-6-8-10-16-12(14)4-2/h3-4H,1-2,5-10H2
    Key: FIHBHSQYSYVZQE-UHFFFAOYSA-N
  • C=CC(=O)OCCCCCCOC(=O)C=C
Properties
C12H18O4
Molar mass 226.272 g·mol−1
AppearanceColorless oil
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H317, H319
P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, P362, P363, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,6-Hexanediol diacrylate (HDDA or HDODA) is a difunctional acrylate ester monomer used in the manufacture of polymers. [1] [2] It is particularly useful for use in ultraviolet light cure applications. [3] Furthermore, it is also used in adhesives, sealants, alkyd coatings, elastomers, photopolymers, and inks for improved adhesion, hardness, abrasion and heat resistance. [4] Like other acrylate monomers it is usually supplied with a radical inhibitor such as hydroquinone added. [5]

Contents

Preparation

The material is prepared by acid-catalyzed esterification of 1,6-hexanediol with acrylic acid. [6]

Other uses

As the molecule has acrylic functionality, it is capable of undergoing the Michael reaction with an amine. This allows it use in epoxy chemistry where its use speeds up the cure time considerably. [7]

See also

Related Research Articles

Acrylates are the salts, esters, and conjugate bases of acrylic acid. The acrylate ion is the anion CH2=CHCO−2. Often, acrylate refers to esters of acrylic acid, the most common member being methyl acrylate. These acrylates contain vinyl groups. These compounds are of interest because they are bifunctional: the vinyl group is susceptible to polymerization and the carboxylate group carries myriad functionalities.

<span class="mw-page-title-main">Acrylic acid</span> Chemical compound

Acrylic acid (IUPAC: propenoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually.

<span class="mw-page-title-main">Trimethylolpropane triacrylate</span> Chemical compound

Trimethylolpropane triacrylate (TMPTA) is a trifunctional acrylate ester monomer derived from trimethylolpropane, used in the manufacture of plastics, adhesives, acrylic glue, anaerobic sealants, and ink. It is useful for its low volatility and fast cure response. It has the properties of weather, chemical and water resistance, as well as good abrasion resistance. End products include alkyd coatings, compact discs, hardwood floors, concrete and cementitious applications, Dental composites, photolithography, letterpress, screen printing, elastomers, automobile headlamps, acrylics and plastic components for the medical industry.

<span class="mw-page-title-main">Alkyd</span> Polyester resin modified by the addition of fatty acids and other components

An alkyd is a polyester resin modified by the addition of fatty acids and other components. Alkyds are derived from polyols and organic acids including dicarboxylic acids or carboxylic acid anhydride and triglyceride oils. The term alkyd is a modification of the original name "alcid", reflecting the fact that they are derived from alcohol and organic acids. The inclusion of a fatty acid confers a tendency to form flexible coatings. Alkyds are used in paints, varnishes and in moulds for casting. They are the dominant resin or binder in most commercial oil-based coatings. Approximately 200,000 tons of alkyd resins are produced each year. The original alkyds were compounds of glycerol and phthalic acid sold under the name Glyptal. These were sold as substitutes for the darker-colored copal resins, thus creating alkyd varnishes that were much paler in colour. From these, the alkyds that are known today were developed.

<span class="mw-page-title-main">Acrylate polymer</span> Group of polymers prepared from acrylate monomers

An acrylate polymer is any of a group of polymers prepared from acrylate monomers. These plastics are noted for their transparency, resistance to breakage, and elasticity.

<span class="mw-page-title-main">Photopolymer</span>

A photopolymer or light-activated resin is a polymer that changes its properties when exposed to light, often in the ultraviolet or visible region of the electromagnetic spectrum. These changes are often manifested structurally, for example hardening of the material occurs as a result of cross-linking when exposed to light. An example is shown below depicting a mixture of monomers, oligomers, and photoinitiators that conform into a hardened polymeric material through a process called curing.

<span class="mw-page-title-main">Acrylic resin</span> Thermoplastic or thermosetting plastic

An acrylic resin is a thermoplastic or thermosetting plastic substance typically derived from acrylic acid, methacrylic acid and acrylate monomers such as butyl acrylate and methacrylate monomers such as methyl methacrylate. Thermoplastic acrylics designate a group of acrylic resins typically containing both a high molecular weight and a high glass transition temperature which exhibit lacquer dry capability. Acrylic resins designed for use in two component systems for crosslinking with isocyanate are referred to as polyols and are made with the monomers previously mentioned as well as hydroxy monomers such as hydroxy ethyl methacrylate. Acrylic resins are produced in different liquid carriers such as a hydrocarbon solvent or water in which case they are referred to as emulsions or dispersions and they are also provided in 100% solids bead form.

Synthetic resins are industrially produced resins, typically viscous substances that convert into rigid polymers by the process of curing. In order to undergo curing, resins typically contain reactive end groups, such as acrylates or epoxides. Some synthetic resins have properties similar to natural plant resins, but many do not.

<span class="mw-page-title-main">Ethyl acrylate</span> Chemical compound

Ethyl acrylate is an organic compound with the formula CH2CHCO2CH2CH3. It is the ethyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced for paints, textiles, and non-woven fibers. It is also a reagent in the synthesis of various pharmaceutical intermediates.

<span class="mw-page-title-main">Melamine resin</span> Hard, thermosetting plastic material often used in dinnerware

Melamine resin or melamine formaldehyde is a resin with melamine rings terminated with multiple hydroxyl groups derived from formaldehyde. This thermosetting plastic material is made from melamine and formaldehyde. In its butylated form, it is dissolved in n-butanol and xylene. It is then used to cross-link with alkyd, epoxy, acrylic, and polyester resins, used in surface coatings. There are many types, varying from very slow to very fast curing.

<span class="mw-page-title-main">Methyl acrylate</span> Chemical compound

Methyl acrylate is an organic compound, more accurately the methyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced to make acrylate fiber, which is used to weave synthetic carpets. It is also a reagent in the synthesis of various pharmaceutical intermediates. Owing to the tendency of methyl acrylate to polymerize, samples typically contain an inhibitor such as hydroquinone.

A thermoset polymer matrix is a synthetic polymer reinforcement where polymers act as binder or matrix to secure in place incorporated particulates, fibres or other reinforcements. They were first developed for structural applications, such as glass-reinforced plastic radar domes on aircraft and graphite-epoxy payload bay doors on the Space Shuttle.

1,6-Hexanediol is an organic compound with the formula (CH2CH2CH2OH)2. It is a colorless water-soluble solid.

Butyl acrylate is an organic compound with the formula C4H9O2CCH=CH2. A colorless liquid, it is the butyl ester of acrylic acid. It is used commercially on a large scale as a precursor to poly(butyl acrylate). Especially as copolymers, such materials are used in paints, sealants, coatings, adhesives, fuel, textiles, plastics, and caulk.

<span class="mw-page-title-main">2-Ethylhexyl acrylate</span> Chemical compound

2-Ethylhexyl acrylate is a colorless liquid acrylate with a pleasant odor, used in the making of paints, plastics and adhesives.

<span class="mw-page-title-main">Pentaerythritol tetraacrylate</span> Chemical compound

Pentaerythritol tetraacrylate is an organic compound. It is a tetrafunctional acrylate ester used as a monomer in the manufacture of polymers. As it is a polymerizable acrylate monomer, it is nearly always supplied with an added polymerisation inhibitor, such as MEHQ.

Waterborne resins are sometimes called water-based resins. They are resins or polymeric resins that use water as the carrying medium as opposed to solvent or solvent-less. Resins are used in the production of coatings, adhesives, sealants, elastomers and composite materials. When the phrase waterborne resin is used, it usually describes all resins which have water as the main carrying solvent. The resin could be water-soluble, water reducible or water dispersed.

1,6-Hexanediol diglycidyl ether is an organic chemical in the glycidyl ether family. It is an aliphatic compound that is a colorless liquid. It has two epoxide (oxirane) groups per molecule. Its main use is in modifying epoxy resins especially viscosity reduction whilst flexibilizing. It is REACH registered.

1,4-Cyclohexanedimethanol diglycidyl ether is an organic chemical in the glycidyl ether family. Its formula is C14H24O4 and the IUPAC name is 2-[[4-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]oxirane. It has the CAS number of 14228-73-0 and is REACH registered in Europe. An industrial chemical, a key use is in the reduction of the viscosity of epoxy resin systems functioning as a reactive diluent.

<span class="mw-page-title-main">Hydroxyethyl acrylate</span> Organic chemical-monomer

Hydroxyethyl acrylate is an organic chemical and an aliphatic compound. It has the formula C5H8O3 and the CAS Registry Number 818–61–1. It is REACH registered with an EU number of 212–454–9. It has dual functionality containing a polymerizable acrylic group and a terminal hydroxy group. It is used to make emulsion polymers along with other monomers and the resultant resins are used in coatings, sealants, adhesives and elastomers and other applications.

References

  1. PubChem. "1,6-Hexanediol diacrylate". pubchem.ncbi.nlm.nih.gov. Retrieved 2020-02-12.
  2. "1,6-Hexanediol diacrylate | C12H18O4 | ChemSpider". www.chemspider.com. Retrieved 2020-02-12.
  3. Ajiboye, Gbenga (2012). "Industrially relevant epoxy-acrylate hybrid resin photopolymerizations". Archived from the original on 2013-11-25.
  4. Abrasion Resistance Testing-Vehicle Exterior Graphics and Pin Striping, SAE International, doi:10.4271/j1847_198906
  5. "13048-33-4 - 1,6-Hexanediol diacrylate, 99% (reactive esters), stab. with 90ppm hydroquinone - HDODA - 43203 - Alfa Aesar". www.alfa.com. Retrieved 2020-02-27.
  6. Ohara, Takashi; Sato, Takahisa; Shimizu, Noboru; Prescher, Günter; Schwind, Helmut; Weiberg, Otto; Marten, Klaus; Greim, Helmut (2003). "Acrylic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_161.pub2. ISBN   978-3527306732.
  7. "Epoxy Polyacrylate Resins". www.hexion.com. Retrieved 2020-02-12.