Feb 5, You should notice that both of them have three double bonds.
Typical uses of plasticized PVC include films, sheets, tubing, coated fabrics, wire and cable insulation and jacketing, toys, flooring materials such as vinyl sheet flooring or vinyl floor tiles, adhesives, sealants, inks, and medical products such as blood bags and tubing, and the like.
Other polymer systems that use small amounts of plasticizers include polyvinyl butyral, acrylic polymers, nylon, polyolefins, polyurethanes, and certain fluoroplastics.
Plasticizers can also be used with rubber although often these materials fall under the definition of extenders for rubber rather than plasticizers. Carraher, Elsevier ; pp. Plasticizers can be characterized on the basis of their chemical structure. However, in the recent past there has been an effort to decrease the use of phthalate esters as plasticizers in PVC, particularly in end uses where the product contacts food, such as bottle cap liners and sealants, medical and food films, or for medical examination gloves, blood bags, and IV delivery systems, flexible tubing, or for toys, and the like.
For these and most other uses of plasticized polymer systems, however, a successful substitute for phthalate esters has heretofore not materialized. One such suggested substitute for phthalates are esters based on cyclohexanoic acid.
In the late 's and early 's, various compositions based on cyclohexanoate, cyclohexanedioates, and cyclohexanepolyoate esters were said to be useful for a range of goods from semi-rigid to highly flexible materials. Other suggested substitutes include esters based on benzoic acid see, for instance, U.
Provisional Patent Application No. Epoxidized soybean oil, which has much longer alkyl groups C16 to C18 has been tried as a plasticizer, but is generally used as a PVC stabilizer. Stabilizers are used in much lower concentrations than plasticizers. Co-pending and commonly-assigned U.
Alcohols useful to esterify the unsaturated cycloaliphatic acid include 2-ethylbutanol and 2-ethylhexanol, and those formed by catalytic addition of carbon monoxide and hydrogen to olefins with subsequent hydrogenation of the resulting hydrocarbons in accordance with the well-known oxo-process.
The unsaturated cycloaliphatic esters used as starting materials can be prepared by subjecting selected cyclic monounsaturated dicarboxylic acids or anhydrides to conventional esterification procedures by reacting the acid or the anhydride with at least one aliphatic monohydric alcohol in the presence of a catalyst.
The cyclic monounsaturated dicarboxylic acids or corresponding anhydrides may be synthesized by a Diels-Alder addition reaction, such as where maleic anhydride is reacted with acyclic or alicyclic dienes, including 1,3-cyclopentadiene yielding nonbridged and bridged compounds, respectively.
The alcohols used to esterify the acid anhydrides may be linear or branched alcohols having carbon atoms or oxoalcohols which are the hydroformulation products of C5 to C12 alkenes. JP discloses tetracarboxylic acid esters as plasticizers, prepared for example from di 2-ethylhexyl ester of 3,6-methylenetetrahydrophthalic acid.
JP discloses compounding a cyclopolyolefin resin with a specific ester compound described by formulae I - IV thereof. The disclosure mentions the diisononyl ester of 3,6-methylenetetrahydrophthalic acid. JP discloses compounding a resin component consisting of a polypropylene-based resin and a polyolefinic thermoplastic elastomer with one or more alicyclic dicarboxylic acid esters of the formula Awherein the ester groups are C alkyl or alkenyl.
To date, none of the prior art compounds or compositions has demonstrated satisfactory equivalence to conventional phthalate plasticizers for use with PVC polymers. Thus what is needed is a method of making a general purpose non-phthalate plasticizer having suitable melting or chemical and thermal stability, pour point, glass transition, increased compatibility, good performance and low temperature properties.The Diels–Alder reaction is an organic chemical reaction (specifically, a [4+2] cycloaddition) between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene derivative.
It was first described by Otto Diels and Kurt Alder in , for which work they were awarded the Nobel Prize in Chemistry in Maleic anhydride is probably hydrolyzed to maleic acid and then hydroxylated to malic acid, which participates in the Krebs cycle or may be excreted unchanged or in conjugated form.
Maleic acid is an antimetabolite of fumaric acid. The Diels–Alder reaction is an organic chemical reaction (specifically, a [4+2] cycloaddition) between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene derivative. It was first described by Otto Diels and Kurt Alder in , for which work they were awarded the Nobel Prize in .
CHAPTER 25 • THE CHEMISTRY OF THE AROMATIC HETEROCYCLES Pyrrole, furan, and thiophene are all much more reactive than benzene in electrophilic aro-matic substitution. Although precise reactivity ratios depend on the particular reaction, the rel-.
Show transcribed image text Cyclopentadiene and maleic acid undergo a Diels-Alder cycloaddition reaction under mild conditions. Select the major product of . Cyclopentadiene and maleic acid undergo a Diels-Alder cycloaddition reaction under mild conditions.
Select the major product of this reaction from the list of structures available%(22).