Technical documentation

Part 1. Synthesis and Properties

Twenty-six alkyl, alkenyl, cycloalkyl, and substituted alkyl 2-cyanoacrylates were synthesized in the pure state. The purity was determined by gas-liquid chromatography, and a correlation between the log retention time and the number of carbons in the compounds within the homologous series was deduced. Their physical properties such as parachor and molar refraction were determined and the data were fitted to a linear relation to the number of carbons present in the ester within a homologous series of cyanoacrylates.

The effect the curing conditions on the properties of adhesive joints formed using cyanoacrylate-based adhesives is investigated. The temperature dependences of relative rigidity and mechanical loss tangent are studied by torque analysis for poly(ethyl-, allyl-, allyloxyethyl-, allyloxyisopropyl-, propargyloxyethyl-, and propargyl-) cyanoacrylates after their thermal treatment in the temperature range of 20–250°C. The glass transition parameters of polycyanoacrylates and the dependence of the curing intensity on the structure of initial monomers and polymers are determined.

Cyanoacrylate polymers are commercially important materials as structural ad- hesives. They combine rapid curing and high strength and are widely used to bond a diverse range of substrate surfaces, including metals, ceramics, plastics, rubbers, and biologically derived materials. The corresponding monomers were first isolated in 1947 by Ardis at B. F. Goodrich (1). Subsequently, Eastman Ko- dak patented them as adhesive compositions in 1957 (2) and the first commer- cial adhesive formulation, based on methyl 2-cyanoacrylate, was introduced in 1958 (3).

Cyanoacrylate Adhesives

Instant adhesives (cyanoacrylate adhesives ) are one-part solvent-free adhesives that cure immediately at room temperature and offer strong bonding strength. Instant adhesive was first developed in 1949 by Alan E. Ardis at Goodrich Company in the U.S., and was later developed into a product by F. B. Joyner and G. F. Hawkins at Eastman Company and marketed as Eastman 910 in 1959. Since then, various adhesive manufacturers around the world have improved and modified methods of synthesizing the main components, monomer.

Cyanoacrylate-Based

Instant Adhesives (cyanoacrylate-based) sets instantly at room temperature, has powerful adhesive strength, has only one easy-to-use component, and contains no dangerous solvents. Development of the adhesive began in 1949 by Alan E. Ardis of Goodrich Corporation in the US. Then in 1959 it was introduced into the market by FB Joyner and GF Hawkins of Eastman Corporation as Eastman 910. Later improvements and modifications of the synthetic method of the major-ingredient monomer were performed by the leading adhesive manufacturers.

Cyanoacrylate Adhesives Vol 2

As already described in Three Bond Technical News 21, instant adhesives are one-part solvent-free adhesives that cure rapidly through polymerization at room temperature. These adhesives are used in a wide range of applications across various industries as a result of their strong adhesive strength. However, instant adhesives includes some disadvantages: low resistance to heat, water, and impact. Numerous patents and reports have been submitted on methods of improving these properties.

US3919083

Water-borne pollutants, particularly those of oelaginous nature, may be treated with monomers which polymerize in the presence of moisture, preferably, monomeric esters of 2-cyanoacrylic acid. Upon polymerization, significant portions of the pollutant are incorporated within a polymer matrix, thus reducing the danger to shore and marine ecology and aesthetics.

US4675273

A method for applying a polymeric resist coating of very high molecular weight to a suitable substrate without the necessity of elaborate purification steps and for ensuring adequate coverage of raised regions in three-dimensionally patterned substrates. The method comprises exposing the substrate to be coated to the vapor of an anionically polymerizable monomer of the formula: CHR=CXY where X and Y are strong electron withdrawing groups R si H or, provided that X and Y are both -CN,C1-C4 alkyl for sufficient time to deposit a polymerizable coating thereon.

Here we report the preparation of mechanically robust silica aerogel polymer nanocomposites using surface-initiated atom transfer radical polymerization. This approach was used to grow poly(methyl methacrylate) (PMMA) with low polydispersities and establish the first structure–property relationship between the grafted PMMA molecular weight and bulk physical properties of the hybrid aerogel.

Strong polymer−silica aerogel composites were prepared by chemical vapor deposition of cyanoacrylate monomers onto amine-modified aerogels. Amine-modified silica aerogels were prepared by copolymerizing small amounts of (aminopropyl)triethoxysilane with tetraethoxysilane. After silation of the aminated gels with hexamethyldisilazane, they were dried as aerogels using supercritical carbon dioxide processing.

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