Ethers, vinyl with anhydrides

A variety of trichloroethylene copolymers have been reported, none with apparent commercial significance. The alternating copolymer with vinyl acetate has been patented as an adhesive (11) and as a flame retardant (12,13). Copolymerization with 1,3-butadiene and its homologues has been reported (14—16). Other comonomers include acrylonitrile (17), isobutyl vinyl ether (18), maleic anhydride (19), and styrene (20). 

In fact, the copolymers of methacrylic acid with maleic anhydride (14) and the copolymers of vinyl alcohol with maleic anhydride (127) obtained respectively from optically active (l-methyl-benzyl)-methacrylate or (l-methyl-benzyl)-vinyl-ether and maleic anhydride, were optically active, but their rotatory power was rather small. 

The processing properties of poly(vinyl chloride) has been improved by copolymerizing vinyl chloride with a small amount of vinyl alkyl ether. Copolymers of vinyl alkyl ethers and maleic anhydride arc used as water soluble thickeners, paper additives, textile assistants and in cleaning formulations. 

Because the urea-urease interaction leads to a pH increase, a polymer that increases erosion rate with increasing pH is needed. A useful polymer for this application is a partially esterified copolymer of methyl vinyl ether and maleic anhydride. This copolymer undergoes surface erosion with an erosion rate that is extraordinarily pH-dependent (J). The polymer dissolves by ionization of the carboxylic acid groups as shown below ... 

Figure 2. Hydrocortisone release rate at 35°C from a n-hexyl half-ester of a copolymer of methyl vinyl ether and maleic anhydride at pH 6.25 in the absence and presence of external urea. No external urea IC M external urea s10 M external urea. (Reproduced with permission from Ref. 2. Copyright 1979, American Pharmaceutical Association.)...

Two examples of diene addition products have been claimed in the literature. Structures 141 and 142 were considered for a 1 1 adduct of anthranil and maleic anhydride, and since 3-phenylanthranil did not react analogously, structure 141 was preferred.271 Also, anthranil and jV-phenylmaleimide have been reported to give compound 143, which with alkali is hydrolyzed and dehydrated to give acridinic acid.272 Attempts to form Diels-Adler adducts between 3-benzoylanthranil and maleic anhydride or n-butyl vinyl ether met with no success.165... 

As can be seen from equations 2-5, the formation of A -acylenamines proceeds from derivatives of carboxylic acids (having an oxidation level equal to three ), namely anhydrides or add halides RCOX or amides RCONH2, on the one hand, and from carbonyl compounds or their derivatives (oxidation level equal to two ), namely enamines 3, acetylenes 5, or vinyl ethers 6, on the other. Indeed, the acetylenes 5, being the dehydration products of enols, may be regarded as having a masked carbonyl functionwhile the enamines 3 rank with vinyl ethers, vinyl esters and enols, as the heteroanalogs of these carbonyl derivatives (see Section IV). 

Fig. 1. Rate of polymer erosion ( ) and rate of hydrocortisone release ( ) from thin disks of an n-butyl half ester of methyl vinyl ether and maleic anhydride at pH 7.4 and 37 °C. Drug loading 10 wt% [1], Reprinted with permission...

Hydrophobic regions can be one or two small, well-defined blocks of pendant hydrophobic moieties in an otherwise water-soluble polymer (2-4). An example is a water-soluble sulfonated BAB triblock copolymer where B is hydrophobic f-butylstyrene and A is vinyltoluene (2). However, hydro-phobic regions can also be less well-defined as well as more numerous in a polymer molecule than is the case for a triblock copolymer (5-22). For example, pendant alkyl esters appear to have been randomly incorporated in styrene-maleic anhydride (5) and vinyl benzyl ether-styrene-maleic anhydride (6-ii) copolymers. Also, alkyl polyoxyethylene acrylate monomers can be copolymerized with acrylamide to yield copolymers with pendant hydrophobic chains (12-15). More recently it was found (16-22) that small amounts of water-insoluble monomers that are solubilized by surfactants into aqueous solutions of a hydrophilic monomer produce copolymers with pendant hydrophobic chains, but the size, number, and nature of the hydro-phobic regions has not been determined. 

The resins of styling or setting products are usually cationic (e.g., polyquatemium-11, a copolymer of vinyl pyrrolidone and dimethy-laminoethyl methacrylate quaternized with dimethyl sulfate, similar to the quatemized copolymer of PVP depicted in Table 7-2), anionic (e.g., butyl ester of polyvinyhnethyl ether and maleic anhydride), neutral (e.g., copolymer of polyvinyl pyrrolidone, vinyl acetate), or even polyvinyl pyrrolidone itself with polyacrylate thickeners. 

This synthetic method has two steps the first step involves synthesising the polymer and the second includes modification with active groups. Some monomers generally used to form the backbone of homopolymers or copolymers include vinyl benzyl chloride, methyl methacrylate, 2-chloroethyl vinyl ether, vinyl alcohol and maleic anhydride. The polymers are then activated by anchoring antimicrobial groups, such as phosphonium salts, ammonium salts or phenol groups, via quaternisation, chloride substitution or anhydride hydrolysis. 

Synonyms 2,5-Furandione, polymerwith methoxyethene 2,5-Furandione, polymer with methoxyethylene Methyl vinyl ether/maleic anhydride copolymer Poly (maleic anhydride-methyl vinyl ether) Poly (methyl vinyl ether-alt-maleic anhydride) Poly(methyl vinyl ether/maleic anhydride) Polyvinyl methyl ether-maleic anhydride PVM/MA Definition Copolymer of methyl vinyl ether and maleic anhydride Empirical (C4H2O3 CsHsO),... 

CAS 31307-95-6 54578-88-0 54077-45-1 56091-51-1 Synonyms 2-Butenedioic acid, polymer with methoxyethene, 1-methylethyl ester Isopropyl ester of PVM/MA copolymer (INCI) Definition Polymer consisting of the partial Isopropyl ester of the polycarboxylic resin formed from vinyl methyl ether and maleic anhydride... 

The nature and the amount of solvent can influence the yield and the composition of the copolymers in these copolymerizations. Copolymerization of phenanthrene with maleic anhydride in benzene yields a 1 2 adduct. In dioxane, however, a 1 1 adduct is obtained. In dimethyl formamide no copolymer forms at all. Another example is a terpolymerization of acrylonitrile with 2-chloroethyl vinyl ether and maleic anhydride or with p-diaxene-maleic anhydride. The amount of acrylonitrile in the teipolymer increases with an increase in the r-electron density of the solvent in the following order ... 

Definition Polymer of maleic anhydride and methyl vinyl ether crosslinked with 1,9-decadiene Uses Binder, film-former, emollient, thickener, stabilizer in detergents, cosmetics Manuf./Distrib. United-Guardian http //www.u-g.com... 

Sodium PVM/MA/decadiene crosspolymer Definition Copolymer of methyl vinyl ether and maleic anhydride crosslinked with 1,9-decadiene Uses Film-former in cosmetics, skin lightening and tanning prods. 

In subsequent developments, Eastman has reported two new alternative manufacturing routes to vinyl acetate (38). The first uses the carbonylation of dimethyl ether to acetic anhydride, followed by the reaction between acetic anhydride and acetaldehyde in a reactive distillation column to 3ueld vinyl acetate, whereas the second involves the intermediacy of ketene. Here ketene is hydrogenated to acetaldehyde, and the acetaldehyde is reacted with a second equivalent of ketene to produce vinyl acetate. Both of these routes are claimed to avoid the problematic and expensive acetic acid recycle. 

Crystallization of cis—1,4-polyisoprene from solution at -65 C has been carried out it is therefore possible that block copolymer preparation by epoxidation, bromination or some other reaction could be accomplished with lamellas of this polymer. Lamellar crystallization of cellulose, of amylose and of polyacrylic acid have been reported substitution reactions such as acetylation or ether formation with the hydroxyl groups and esterfication of the acid groups are possible reactions to carry out with lamellas of those polymers. The use of nonaqueous systems may be better suited to prevent swelling, and therefore, attack of the crystalline regions. It should also be possible to react poly(vinylalcohol) lamellas in suspension with acids or anhydrides to form vinyl-alcohol-vinyl ester block copolymers or with phosgene to obtain chloroformate groups which can undergo further reactions. 

St/N-substituted maleimides [221,230], MA/isobutene and MA isobutyl vinyl ether [236], iso-Bu vinyl ether (iBVE) with electron-withdrawing monomers such as maleic anhydride and N-substituted... 

Other monomers that copolymerize with alkyl vinyl ethers are vinyl ketones [47], acrolein diacetate [48], acrylamide [49], alkoxy 1,3-butadienes [50], butadiene [51], chloroprene [52], chlorotrifluoroethylene [53], tri-and tetrafluoroethylene [54], cyclopentadiene [55], dimethylaminoethyl acrylate [56], fluoroacrylates [57], fluoroacrylamides [58], A-vinyl car-bazole [59,60], triallyl cyanurate [59,60], vinyl chloroacetate [61,62], N-vinyl lactams [63], A-vinyl succinimide [63], vinylidene cyanide [64, 65], and others. Copolymerization is especially suitable for monomers having electron-withdrawing groups. Solution, emulsion, and suspension techniques can be used. However, in aqueous systems the pH should be buffered at about pH 8 or above to prevent hydrolysis of the vinyl ether to acetaldehyde. Charge-transfer complexes have been suggested to form between vinyl ethers and maleic anhydride, and these participate in the copolymerization [66]. Examples of the free-radical polymerization of selected vinyl ethers are shown in Table IV. 

Another route towards biomolecular functionalisation of switchable cell culture carriers was proposed by Gramm et al. (2011). The thermo-responsive polymer poly (vinyl methyl ether) was blended with a small amount of the alternating copolymer of vinyl methyl ether and maleic anhydride. After electron beam cross-linking, stable films with a dry thickness of up to 70 nm were obtained. The introduced anhydride moieties allow for subsequent protein or peptide immobilization without toxic coupling agents. This concept was applied and further developed by Teich-mann et al. (2013). The impact of different adhesion-promoting molecules immobilised in different concentrations to the thermo-responsive coating was evaluated and compared. 

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