Maleic acid - vinyl ether

Alkenylsuccinic anhydrides made from several linear alpha olefins are used in paper sizing, detergents, and other uses. Sulfosuccinic acid esters serve as surface active agents. Alkyd resins (qv) are used as surface coatings. Chlorendric anhydride [115-27-5] is used as a flame resistant component (see Flame retardants). Tetrahydrophthalic acid [88-98-2] and hexahydrophthalic anhydride [85-42-7] have specialty resin appHcations. Gas barrier films made by grafting maleic anhydride to polypropylene [25085-53-4] film are used in food packaging (qv). Poly(maleic anhydride) [24937-72-2] is used as a scale preventer and corrosion inhibitor (see Corrosion and corrosion control). Maleic anhydride forms copolymers with ethylene glycol methyl vinyl ethers which are partially esterified for biomedical and pharmaceutical uses (189) (see Pharmaceuticals). 

The strength of ion binding is enhanced when the arrangements of the functional groups permit chelate formation (Begala Strauss, 1972). Thus, magnesium is more firmly bound to poly(vinyl methyl ether-maleic acid) than to either poly(acrylic acid) or poly(ethylene maleic add). 

Experimental studies of the adsorption of polyelectrolyte have been reported by several authors Pefferkom, Dejardin, and Varoqui (3) measured the hydrodynamic thickness of an alternating copolymer of maleic acid and ethyl vinyl ether adsorbed on the pore walls in cellulose ester filter as a function of the molecular weight and the concentration of NaCl. Robb et al. (4) studied the adsorption of carboxy methyl cellulose and poly (acrylic acid) onto surfaces of insoluble inorganic salts. However, their studies are limited to the measurements of adsorbance and the fraction of adsorbed segments. 

St styrene, MMA methyl methacrylate, IB isobutene, VAc vinyl acetate, VC1 vinyl chloride, DiPF diisopropyl fumarate, AA acrylic acid, MAn maleic anhydride, IBVE isobutyl vinyl ether. 

Crosslinking of amine- or hydroxy-terminated PAMAM dendrimers using cyclic anhydride - amine or cyclic anhydride - hydroxy addition reactions was employed for preparation of crosslinked thin films of very low permeability [73], Polyanhydrides, such as maleic anhydride-methyl vinyl ether copolymers, were used as crosslinking components. In the case of amine-terminated PAMAM, crosslinking and chemical stability were further increased by imidization of the maleamic acid groups retro-Michael eliminations were followed by Michael additions to further crosslink the film. 

Crasto, A.S., Own, S.H. and Subramanian, R.V. (1988). The influence of the interphase on composite properties Poly(cthylene-co-acrylic acid) and poly(methyl vinyl ether-co-maleic anhydride) electrode-posited on graphite fibers. Polym. Composites 9, 78-92. 

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. 

MVE/MAN Copolymem. Various iuol wl grades of polv(melliyl vinyl ether-co-maleic anhydride) (PMVEMA) are available. PMVEMA, supplied as a white, fluffy powder, is soluble in ketones, esters, pyridine, lactams, and aldehydes, and insoluble in aliphatic, aromatic, or halogenated hydrocarbons, as well as in ethyl ether and nitroparaffins. When the copolymer dissolves in water or alcohols, the anhydride group is cleaved, forming the polymers in free acid form or the half-esters of the corresponding alcohol, respectively. 

Poly(methyl vinyl ether-co-maleic acid) (PMVEMAC)... 

Narayanan, K.S., M. Singh, and R.K. Chaudhuri (1993). The reduction of herbicide leaching using vinyl pyrrolidone copolymers and methyl vinyl ether maleic acid ester copolymers. In P.D. Berger, B.N. Devisetty, and F.R. Hall, eds., Pesticide Formulations and Application Systems, Vol. 13. Philadelphia, PA American Society for Testing and Materials, pp. 57-75. 

As pointed out by Heller (2), polymer erosion can be controlled by the following three types of mechanisms (1) water-soluble polymers insolubilized by hydrolytically unstable cross-links (2) water-insoluble polymers solubilized by hydrolysis, ionization, or protonation of pendant groups (3) hydrophobic polymers solubilized by backbone cleavage to small water soluble molecules. These mechanisms represent extreme cases the actual erosion may occur by a combination of mechanisms. In addition to poly (lactic acid), poly (glycolic acid), and lactic/glycolic acid copolymers, other commonly used bioerodible/biodegradable polymers include polyorthoesters, polycaprolactone, polyaminoacids, polyanhydrides, and half esters of methyl vinyl ether-maleic anhydride copolymers (3). 

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 ... 

Vinyl chloride can be copolymerized with a series of monomers Vinylidene chloride, trans-dichloroethylene, vinylesters of aliphatic carboxylic acid (C2-C18), acrylic acid esters, methacrylic and/or maleic acid as well as fumaric acid with mono-functional aliphatic saturated alcohols (Cj-C18), mono-functional aliphatic unsaturated alcohols (C8—C18), vinyl ethers from mono-functional aliphatic saturated alcohols (C i-Cis), propylene, butadiene, maleic acid, fumaric acid, itaconic acid, acrylic acid, methacrylic acid (total < 8 %) and N-cyclohexylmaleinimide (< 7 %). 

Several polymers were found to fit all or most of the above criteria and were used to prepare the carrier films. Many polymers have been used for this purpose, viz., ethyl cellulose, poly(y-benzyl glutamate), poly(vinyl acetate), cellulose acetate phthalate, and the copolymer of methyl vinyl ether with maleic anhydride. In addition to the base polymers, plasticizers were often needed to impart a suitable degree of flexibility. Plasticizers, which are found to be compatible with polymeric materials include, acetylated monoglycerides, esters of phthalic acid such as dibutyl tartarate, etc. An excipient was usually incorporated into the matrix of the carrier films. The excipients used were water-soluble materials, which are capable of creating channels in the polymer matrix and facilitate diffusion of the drug. PEGs of different molecular weights were used for this purpose. 

Research on nasal powder drug delivery has employed polymers such as starch, dextrans, polyacrylic acid derivatives (e.g., carbopol, polycarbophil), cellulose derivatives (microcrystalline cellulose, semicrystalline cellulose, hydroxypropylmethyl cellulose, hydroxypropyl cellulose, carboxymethyl cellulose), chitosan, sodium alginate, hyaluronans, and polyanhydrides such as poly(methyl vinyl ether-co-maleic anhydride) (PVM/MA). Many of these polymers have already been used as excipients in pharmaceutical formulations and are often referred to as first-generation bioadhesives [38-45], In nasal dry powder a single bioadhesive polymer or a... 

Poly(vinyl alcohol) is utilized as a component of starch-based adhesives.11121114 Other patents report the use of partially oxidized starch,1115 dextrins,1116 dextrins and urea,1117 borax,1118 boric acid,1119 and vinyl methyl ether-maleic acid copolymers.1120 Other patents indicate the use of poly (vinyl alcohol) with partially hydrolyzed poly(vinyl acetate),1121 nonhy-drolyzed poly(vinyl acetate),1122 and poly(vinyl chloride).1123 A few patents have reported such poly acrylic additives as poly (acrylic acid)1124 and its salts,1125 poly(acrylamide),1126 1127 A-methylacrylamide or poly(A-acryl-amide),1128 and polyethyleneimine.1129 Polystyrene has also been used,1130 as well as more complex copolymers such as a maleic acid monobutyl ester-methyl vinyl ether copolymer, together with dextrin and polyacrylamide),1131 carboxylated ethyl acrylate-styrene zinc salt copolymer,1132 ethylene-methyl acrylate-vinyl acetate copolymer,1133 vinyl acetate-vinyl pyr-rolidone copolymer,1134 and ethylene-vinyl acetate copolymer.1135 Some adhesives are compounded with SBR latex1136 1138 and phenol-formaldehyde resins.1139... 

In a very recent publication, Bergbreiter, and co-workers studied the extension of this concept using the pH value as a regulatory variable [20 b]. A phosphine-modified polyacid (a copolymer from methyl vinyl ether and maleic acid anhydride, Gantrez ) was taken as a ligand for rhodium. The rate of hydrogenation of various unsaturated substrates was reversibly modified by tuning the pH value. 

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... 

Poly(methylvinyl ether/maleic anhydride) and related free acids are hygroscopic powders and therefore excessive exposure to moisture should be avoided. Aqueous solutions exhibit decreases in viscosity upon exposure to UV light. Polyfmethyl-vinyl ether/maleic anhydride) should be stored in a cool, dry place out of direct sunlight. 

PVP forms molecular adducts with many substances. Insoluble complexes are formed when aqueous solutions of PVP are added to tannic acid, poly(acrylic acid) and methyl vinyl ether-maleic anhydride copolymer. Soluble complexes, called iodophors, are formed with iodine the solubility of iodine is increased from 0.034% in water at 25°C to 0.58% by 1% PVP. The resulting iodophor retains the germicidal properties of iodine. It is thought that the iodine is held in a PVP helix in solution. The influence of two samples of PVP on the solubility of testosterone is shown in Fig. 8.21. The PVP correspondingly increases the rate of solution of the steroid from solid dispersions. 

U.S. 5188752 (1993) [58] Prencipe et al. (Colgate-Palmolive) Crosslinked methyl vinyl ether—maleic anhydride copolymer fatty acid/salt Linear, viscoelastic... 

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