English

Disclosed are processes for sterilization of cyanoacrylate adhesive compositions, the compositions, comprising 2-cyanoacrylate ester monomers, so produced and a method for assaying the effectiveness of the sterilization process. The process comprises heating the adhesive composition to from about 70° C. to about 140° C. for an effective amount of time.

A method is provided for sterilizing materials, particularly polymers, for drug delivery and implantation, wherein the material is treated with supercritical fluid carbon dioxide at pressures in the range of 2000 to 3000 psi (140 to 210 bar) and temperatures preferably between 30 and 45.degree. C. for periods between 20 minutes and six hours, more preferably between 0.5 and 2 hours.

The concept of channels has been with us more than a century. For half a century, biologists have studied the remarkable workings of protein and peptide channels that permit various cations and small molecules to pass through the phospholipid bilayer membrane. During the past decade, attempts have been made by chemists and biochemists to examine the action of channel compounds from the chemical point of view and to model their function using synthetic structures.

Calix[4]arenes in their 1,3-alternate conformation are particularly convenient scaffolds for the construction of extended tubes. These molecules can act as polytopic cation receptors and have the fascinating property of allowing cation transport |("shuttling") along the tube by passing through the "π-basic tube" formed by the macrocyclic rings of the calixarene units. Although calix tubes can also influence anion transport, this does not appear to involve anion shuttling.

The use of CO2 under pressure (dense CO2) is one of the most promising techniques to achieve cold pasteurization and/or sterilization of liquid and solid ma- terials, and is likely to replace or partially substitute currently and widely applied thermal processes. Although the ability of CO2 to inactivate microorganisms has been known since the 1950s, only within the last 15 years it has received special attention, and the scientific and economic interest towards practical applications is presently growing more and more.

Sterility is required for medical devices use in invasive medical procedures, and for some situations in the food industry. Sterilization of heat- sensitive or porous materials or devices, such as endoscopes, porous implants, liquid foodstuff, and liquid medicine, poses a challenge to current technologies. There has been a steady interest in using high-pressure carbon dioxide as a process medium for new sterilization technology. Among the potential advantages are that CO2 may sterilize at low temperatures.

Microorganisms produce secondary metabolites like trichloroanisole (2,4,6-TCA), but also other unpleasant substances, which cause the typical “cork taint” in wine. This has led to serious problems for the cork industry in recent years and market share of cork stoppers decreased continuously. Conventional processes to reduce TCA content were only partly successful. Therefore a research program was started using supercritical CO2 in order to reduce the TCA content below the detectable limit.

A sterilized cyanoacrylate adhesive composition including a cyanoacrylate composition and a cure speed enhancer, wherein said sterilized cyanoacrylate adhesive composition does not cure upon sterilization, and wherein the composition when cured to form a film on a patient's tissue has water vapor transmission rate from about 950 to about 3000 g/m2/day.

An adhesiv ecompostion includes compounds having the following formula:

-----

wherein R1 is alkyl, alkoxy alkyl, anhydride, ether, ester, or amide, and R2 and R3 are hydrogen, alkyl, alkoxy alkyl, hydroxy, alkenyl, ester, carboxylic acid or ether and wherein R1 is optionally omitted where R2 and R3 are not both hydrogen.