Vinylether Monomer
We manufacture vinyl ether monomer using acetylene obtained from our ethylene plant as a raw material. The vinyl ether monomer is manufactured by allowing acetylene to react with alcohol under basic catalyst.
This method is generally called the Reppe reaction.
Features of vinyl ether monomer
- It has lower viscosity and lower surface tension in comparison with (meth)acrylate monomer with a similar structure.
- It has lower irritation in comparison with (meth)acrylate monomer with a similar structure.
- It has various reactivities and capable of synthesis of copolymer with various monomers.
Introduction to our products and development products
- We have achievements in the various types of synthesis, such as monovinyl ether, divinyl ether, and vinyl ether containing the hydroxyl group.
- We have achievements in the syntheses of vinyl ether monomers other than those listed in the table responding to the inquiries of customers. If you request a sample, inquire of the Chemical 2 Group for products and of the Project Development Section for development products.
E-mail：strategy@chemiway.co.jp
Expected application
- Ink, paint, and developing agents
- Adhesive tape, adhesive agents, and sheets
- Imprint, resist, optical members, and electronic material members
Materials using vinyl ether are reported in many patent gazettes, and their usefulness is verified. Click here to see a list of patent gazettes prepared by us.
Information on properties
Viscosity
- Vinyl ether monomer has lower viscosity in comparison with (meth)acrylate monomer with a structure similar to these.
- It is easy to handle because of low viscosity, and also useful as a viscosity adjusting agent.
Surface tension
- Vinyl ether monomer has lower surface tension in comparison to (meth)acrylate monomers with a structure similar to these.
- It has good wettability because of low surface tension and is expected to contribute to the improvement of adhesive strength.
Various reactivities
Although cation polymerizability of vinyl ether monomers is well known generally, a part of the vinyl ether has radical polymerizability. Since we have our unique patent technology, ask us (Project Development Section).
Vinyl ether can perform not only homopolymerization but also copolymerization with glycidyl ether monomer and acrylate/ methacrylate monomer, and it performs complete alternating copolymerization with monomers with high electron accepting property (fluoroolefin and maleic anhydride).
In addition, vinyl ether monomer has reactivity with various reactive functional groups, such as the acetalization reaction and enethiol reaction.
Example of reaction
Cation polymerization (Cooperative research with Osaka University Graduate School of Science Aoshima Laboratory) →Link to Web site of Aoshima Laboratory
Homopolymerization system: Living cation polymerization
- Since the side chain of vinyl ether has electron donating property, cation polymerizability of vinyl ether is high, and the narrowly distributed polymer where the array is controlled by living cation polymerization can be synthesized.
<Example of patent> ABA type triblock copolymer and its manufacturing method. Patent No. 5662526
Copolymerization system: Vinyl-added ring-opening cation polymerization with oxirane
- It has been said that copolymer of vinyl ether and oxirane (epoxide) is not produced.
- As a result of studying copolymers using isobutylene oxide (IBO), which is comparatively stable at ring-opening, vinyl-added ring-opening cation copolymerization was achieved.
Copolymerization system: Controlled cation alternating copolymerization with aldehydes
- Since ceiling temperature of polymerization of aldehyde is low and homopolymerizability is low, copolymers with vinyl ether and high reactivity were not obtained in cation polymerization.
- When we examined copolymerization of aromatic aldehydes and vinyl ether using a new initiator system, we discovered that an alternating copolymer was obtained.
Radical polymerization (Cooperative research with Fukui University Graduate School of Engineering Sugihara Laboratory) →Link to Sugihara Laboratory Web site
Homopolymerization system: Synthesis of radical polymer by radical stabilization
- Radical polymerizability of vinyl ether is said to be low.
- Since the electron-donating property is lowered and radicals are stabilized when the ether oxygen of vinyl ether and the substance that performs the hydrogen bond are made to coexist, acquisition of the polymer was enabled.
<Example of patent> Method for manufacturing oxyethylene chain-containing vinyl ether polymer by radical polymerization. Patent No. 7016072
Copolymerization system: Copolymerization with maleic anhydride
- Vinyl ether forms alternating copolymers by performing radical polymerization under coexistence of maleic anhydride.
- Since the vinyl group has a high electron-donating property, it forms a charge-transfer complex with the maleic anhydride monomer, which has a high electron-accepting property, and proceeds polymerization.
Copolymerization system: Copolymerization with fluorine monomer
- Vinyl ether obtains a copolymer with high alternating property by performing radical polymerization with fluoroolefin and its high electron-accepting property.
- Alternating copolymerization of the fluorine monomer and vinyl ether improves the solubility in a solvent and dispersibility of the pigment.
Low molecular reaction
Ene-thiol reaction
- In the enethiol reaction, thiyl radicals are added to the double bond of vinyl ether nucleophilicly.
- It is said that vinyl ether reacts easier than acrylic ester.
Acetalization reaction/acetal protection
- Alcohol and carboxylic acid can be protected in the form of acetal by the reaction of vinyl ether.
- Deprotection of acetal is generally performed by acid hydrolysis.
Information on Patent Gazettes
Materials using vinyl ether are reported in many patent gazettes, and their usefulness is verified.
Since they are used in various types of applications, we hope you refer to these for your application.
Ink, paint, developing agent, etc.
Adhesive tape, adhesive agents, sheets, etc.
Imprint, resist, optical member, electronic material member, etc.
Other
Vinylphosphonate Monomer
Vinyl phosphonate monomer is manufactured by the hydrophosphorylation reaction of acetylene.
Features of vinyl phosphonate monomer
- Phosphonic acid unit forms a chemical bond with metal surface.
- Aqueous treatment to titanium, aluminum, etc. can be performed.
- Surface treatment can provide functions, such as rust-preventive property and radical reactivity.
- Phosphoric acid ester is known as a phosphorous flame retardant.
- Copolymerization with a macromolecular monomer and mixing of a homopolymer can provide high flame retardancy.
- There are the phosphonic acid unit and vinyl group, as well as the substituent with two types of different reactivities.
Introduction to our development products
- If you are interested, please feel free to ask us. (Project Development Section)
- Since our products may correspond to regulated substance listed in Foreign Exchange and Foreign Trade Control Law, please inform us when you export them.
E-mail：strategy@chemiway.co.jp
Expected application
Surface treatment agent, chelating agent, detergent, adhesive property improver, dispersing agent and dental material